64 Of The Best Movies To Stream On Amazon Prime Video In October
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1.(500) Days of Summer (2009)
Perhaps the most outstanding thing about (500) Days of Summer — more so than the incredible indie soundtrack, Zooey Deschanel's "manic pixie dream girl" rise to fame, and that it makes every person walking through Ikea pretend that it is their dream house — is that every time you watch it, a different member of the romantic couple is the villain. Is Joseph Gordon-Levitt's Tom too idealistic, clingy, controlling, and unrealistic? Is Deschanel's Summer leading him on, afraid of commitment, and toying with his feelings? Everyone you ask has a different (VERY STRONG) opinion. The beauty of the script and performances, however, is that it accurately portrays an ill-fated relationship where neither party is the hero or the villain. They're just both people who at that time are not compatible, for whatever reason. You've just never seen it on film before.
Watch it now on Amazon Prime.
2.Anaconda (1997)
Jennifer Lopez is having a moment. She’s back with Ben Affleck. She’s looking younger than ever. And we can’t forget the Super Bowl halftime show and award-winning performance in Hustlers from the prepandemic days. I’d therefore like to take this opportunity to highlight a cult classic B-movie gem starring Ms. Lopez. In Anaconda, J.Lo stars as a documentary filmmaker searching for an Indigenous tribe in the Amazon, only to stumble upon a massive killer anaconda. The horror film is a schlocky romp with Ice Cube, Owen Wilson, and Danny Trejo all making appearances as well. I’d highly recommend watching this in a group setting because screaming and laughing while watching an anaconda digest a human is always more fun with others.
Watch it on Amazon Prime.
3.Annette (2021)
Let me say right off the bat that this is NOT a film for everyone. The rock opera musical from French auteur Leos Carax (Holy Motors) performed well among the elite cinephiles present at its Cannes Film Festival premiere, but its polarizing, slightly obtuse nature will make it a difficult sit for many. Adam Driver plays an edgy stand-up comedian who falls in love with Marion Cotillard’s opera singer. While Driver and Cotillard throw the full force of their acting powers into the roles, to mesmerizing effect, the structure of the movie, mimicking that of an opera, is much slower than a traditional movie musical. For those in love with French cinema and looking for a challenge, however, this could be a rewarding way to spend an evening.
Watch it on Amazon Prime.
4.Arrival (2016)
It is still difficult for me to think of Arrival without thinking of Amy Adams’ egregious Oscar snub for the role. Should have won the category but wasn’t even nominated. But I’m getting sidetracked. This Best Picture nominee directed by Denis Villeneuve (whose Dune comes out this fall) focuses on a linguist (Adams) who is asked to help communicate with aliens, using their inkblot language, when giant spaceships touch down on Earth. The grounded sci-fi film is exquisitely shot and features an entrancing score. This is also the film that gave us the classic Amy Adams–with–a–whiteboard meme.
Watch it on Amazon Prime.
5.*Atonement (2006)
I'd like to start by saying that Keira Knightley's green dress in Atonement is one of the greatest pieces of modern cinematic costume design ever. To watch her float around that mansion in the film's early scenes is better than anything going on at Paris Fashion Week — and the costumes deservedly scored the film one of its seven Oscar nominations. This epic romance, based on the bestselling Ian McEwan novel, details one tragic dinner party and how the events that transpire haunt those present for decades to follow. Saoirse Ronan makes her splashy Oscar-nominated breakthrough on the world stage, James McAvoy is looking as dapper as ever, and that sex scene in the library! My god, what else can you ask for from a film?
Watch it on Amazon Prime.
6.*The Best Exotic Marigold Hotel (2012)
If Dame Maggie Smith decides she's going to India, then by golly, I'm going to India with her. In this delightful romantic comedy aimed at a more, shall we say mature, audience, Smith's Muriel moves to a retirement home in India along with a posse of fellow British pensioners (that is a UK phrase if I've ever heard one). The ragtag group is, of course, full of English acting royalty, including Old Deuteronomy herself Dame Judi Dench, Davy Jones sans tentacle beard Bill Nighy, and feisty Cousin Isabel Penelope Winton. The titular hotel is, of course, run by the dreamy Dev Patel, who fosters the group's various romances and adventures. Don't let the cast's average age fool you — this is a romp for the whole family if you can swallow a few jokes about taking pills.
Watch it on Amazon Prime.
7.The Big Sick (2017)
So let’s say you dated a girl for five months and then she broke up with you. And then she went to the hospital and was put into a coma. And then her parents came and they knew you broke up. And then you just had to sit with them awkwardly in the waiting room because you did still care about the girl. Thus is the premise of The Big Sick, and also the real-life events surrounding the romance of the film's writers, Emily V. Gordon and Kumail Nanjiani (who is also the star). One of the best romantic comedies of the past decade, this film also examines interracial dating in a smart, nuanced way and is stacked with your comedy faves, including Holly Hunter, Ray Romano, and Bo Burnham (whose recent comedy special Inside is a masterpiece). Now is also a great time to watch The Big Sick, as ripped Nanjiani will be in Marvel’s Eternals this fall.
Watch it on Amazon Prime.
8.Bottle Shock (2008)
Once upon a time, I was home for the summer from college and rented this film from the library because I love Alan Rickman (Harry Potter, Robin Hood: Prince of Thieves, Sense and Sensibility; I could go on). I found the movie captivating and demanded the DVD for Christmas. Rickman stars as a snobbish connoisseur of French wine who decides to throw a competition between the lauded French wineries and the looked-down-upon Californian upstarts (the leads of whom are Bill Pullman and Chris Pine). Rickman is an absolute delight, and I (someone who buys $4 watermelon rosé from Trader Joes) was mesmerized by the true story that put Napa Valley on the map in the ’70s. Perhaps uncork a bottle of wine and settle in for the evening?
Watch it on Amazon Prime.
9.Brittany Runs a Marathon (2019)
As somewhat of a marathon expert (I’ve written a whole book about the sport), I can personally attest to the tremendous amount of work that goes into running 26.2 miles, as well as the euphoric emotional payoff of finishing. This Jillian Bell film (based on a true story) follows Brittany as she signs up for the New York City Marathon in an attempt to get her life back on track. The heartwarming comedy also stars Michaela Watkins (Search Party) and Utkarsh Ambudkar (Pitch Perfect) and is the first feature film to actually shoot on location during the marathon. Watching Brittany finish her race is incredibly inspiring and will make you want to sign up for a marathon as well.
Watch it on Amazon Prime.
10.Burn After Reading (2008)
The Coen Brothers know how to perfectly entangle in-over-their-heads yokels into a high-stakes crime plot. And reminiscent of Fargo or No Country for Old Men (although much less serious than the latter), here they focus on a pair of dunderheaded gym employees — the gun-chomping Chad Feldheimer (Brad Pitt) and the plastic surgery–obsessed Linda Litzke (three-time Oscar winner Frances McDormand) — into a CIA conspiracy. George Clooney, John Malkovich, and Tilda Swinton are also quickly caught up in the drama, and before you know it, there’s a dead body in the closet and a government cover-up. I’m still slightly infuriated that this film didn’t get more awards-season love. Pitt should have landed at least a nom for this GIF alone.
Watch it on Amazon Prime.
11.Burning (2018)
Yes, this is a two-and-a-half-hour Korean film with subtitles, but BOY OH BOY, is it worth it. Watching Burning, which is based on the short story “Barn Burning” by Haruki Murakami, was one of the most enjoyable viewing experiences I’ve had in recent memory. The film (which the Oscars snubbed) begins as a lyrical love story between Jong-Su (Yoo Ah-in) and Hae-mi (Jeon Jong-seo), but just as the two seem to have found a rhythm, they are interrupted by the suave, charismatic Ben (Minari’s Oscar-nominated Steven Yeun). Not knowing what will happen is the beauty of this film, so I won’t say more, but like Parasite, it pivots into something more mysterious, subverting expectations repeatedly along the way. Please do yourself a favor and go stream it.
Watch it on Amazon Prime.
12.*Butch Cassidy and the Sundance Kid (1969)
If you're looking to cross another classic off your to-watch list, then this Western is ripe for the taking. The film, which consistently shows up on "Best Movies Ever" lists, stars Hollywood legends Paul Newman and Robert Redford as outlaws Butch Cassidy and the Sundance Kid. After a string of train robberies leaves them in the crosshairs of the authorities, the pair go on the run, outwitting and outshooting the investigators hot on their trail. The film was nominated for seven Oscars (including Best Picture) and remains a watchable caper to this day.
Watch it now on Amazon Prime.
13.Climax (2018)
Let’s just say this: If you’re having a rave in a secluded old schoolhouse in the middle of winter, PRAY that the punch is not spiked with LSD. This psychological horror film, starring Miss Blades-for-Legs from Kingsman herself, Sofia Boutella, begins innocent enough when a French dance troupe gathers for a party post-rehearsal. As the effects of the drugs take hold, however, the night speeds into a dark and bloody haze set to the pulsing beats of house music. The opening dance sequence is something to behold, whether or not you have the stomach for where the film ventures later. The cast are all trained dancers rather than actors, and the long takes allow them to fully showcase their moves…before they die.
Watch it on Amazon Prime.
14.Clockwatchers (1998)
Not to be confused with Clockstoppers, the 2002 film about teens with magic watches, Clockwatchers is a ’90s comedy about four women who become friends working as temps together at an office. Parker Posey is the feisty ringleader of the group, which also includes Phoebe Buffay herself, Lisa Kudrow; Euphoria’s Alanna Ubach; and the world’s greatest living actor, Toni Collette. When a string of office thefts throws suspicion onto the women, they must band together, forming new bonds, overcoming obstacles, and solving the workplace mystery in the process. This list is basically just your syllabus for watching Toni Collette films, and this is a great place to start.
Watch it on Amazon Prime.
15.Closer (2004)
Oh, what a tangled web this movie is. Jude Law falls in love with Natalie Portman. But then also Julia Roberts. But then Julia Roberts is with Clive Owen. Until she leaves him for Jude Law. Who leaves Natalie Portman. Who then sleeps with Clive Owen. Who wants to get back with Julia Roberts. Basically, this foursome is a HORNY MESS of beautiful people trying to figure out their lives and relationships, and we're just along for the ride. All four of these Oscar-nominated actors are at the peak of their game, with Portman shining especially bright. A fascinating character study with juicy dialogue and exquisite early-aughts fashion, this is a film not nearly enough people are talking about.
Watch it now on Amazon Prime.
16.Cold War (2018)
The first time I tried to see Cold War in theaters, I had to leave 10 minutes in because the man sitting behind me said he’d found bedbugs in his chair. Nevertheless! I had such high hopes for the movie that I booked a ticket at a different theater the next day (after nuking my clothes in the dryer and scrubbing down in the shower), and I was not disappointed. This Oscar-nominated Polish film from Pawel Pawlikowski follows the star-crossed 20-year romantic saga of Zula and Wiktor during the Cold War. Shot in stark black-and-white, the story is as beautiful as it is heartbreaking. A romance for the ages.
Watch it on Amazon Prime.
17.*Die Hard (1988)
Please weigh in on the cultural debate. Is Die Hard a Christmas movie? Every year when the holidays roll around and new lists of best Christmas movies arrive, the issue is drudged back up. Is the Bruce Willis–helmed action film about a cop stopping a terrorist attack on Christmas Eve technically a "Christmas movie" or a "movie set on Christmas"? The debate rages on. Either way, the caper, which sees Willis crawling around in air ducts and Alan Rickman pontificating as iconic villain Hans Gruber, is extremely watchable. There are bona fide Christmas films *cough* It's a Wonderful Life *cough* that are much more of a slog to get through. Christmas films would be lucky to have Die Hard. So "Yippee ki-yay" to that, Mother Marys.
Watch it on Amazon Prime.
18.Do the Right Thing (1989)
Many films begin to lose cultural relevance the moment they leave the theater (if they ever even had any to begin with), but Spike Lee's early masterpiece only seems to gain relevance with each passing day. Lee stars in the film — which he also wrote, directed, and produced — as Mookie, who wanders around Bed-Stuy, Brooklyn, on a blistering-hot summer day. He shows us the neighborhood and its eclectic inhabitants as the heat and tension between the Black and Italian community members rise. The way the film stares racial violence square in the face made many people uncomfortable when it was released, leading to its largely being snubbed at awards shows. The film has only grown in stature over the years, however, as the problems addressed in 1989 continue to plague the nation. Do the Right Thing is more than just a great film — it is a necessary indictment of the world we live in.
Watch it now on Amazon Prime.
19.*Duplicity (2009)
A film about two cosmetics companies racing to find the cure for balding doesn't sound all that interesting. But what if we took two government spies with a romantic past, put them into the private sector as corporate agents of espionage, and had them battle it out to steal the opposing brand's hair loss miracle treatment? Sound more interesting? Or at least camp enough that you want in? The pair of romantic spies are played by Julia Roberts and Clive Owen, with the never disappointing Paul Giamatti as the head of one of the corporate brands. The fizzy, twisty film is an entertaining puzzle for viewers to piece together, and if you're not into that, you can at least watch spies fall in love.
Watch it on Amazon Prime.
20.Everybody's Talking About Jamie (2021)
If you're a musical and you can get me listening to your song on repeat for a week, then you've got my support. And my Spotify certainly knows I've been jamming to "And You Don't Even Know It" nonstop. The film, based on the smash hit, Olivier Award–nominated West End musical, follows a teenage boy named Jamie (newcomer Max Harwood) who dreams of becoming a drag queen. The songs are certified bops, and the glitzy choreography is a joy to watch. The supporting cast — including the never-bad Richard E. Grant as his drag mentor, Sarah Lancashire as the supportive mother every queer kid wishes they had, and Lauren Patel as Jamie's peppy best friend — also bolsters the film. Inject this kind of pure, wholesome, LGBTQ fun straight into my arm, please.
Watch it now on Amazon Prime.
21.The Farewell (2019)
Apparently, in China it is not an uncommon practice to hide death prognoses from patients in hopes that they will have a higher quality of life as they near life’s end. In this film, directed by Lulu Wang and based on her life, the Wang family receive news that the matriarch, Nai Nai, has terminal lung cancer. Instead of sharing that news, they decide to stage a wedding as an excuse to bring the whole family to China to see their grandmother one final time. Billi (Awkwafina) tags along but is extremely uneasy about lying to her grandmother so excessively. What transpires will make you not only laugh but also cry, sigh, smile, and feel a gamut of other emotions as the film looks at the importance of family and the ends we’ll go to to protect the ones we love.
Watch it on Amazon Prime.
22.Fast Times at Ridgemont High (1982)
You can never have enough ’80s high school comedies, and Fast Times at Ridgemont High fits in perfectly with the Ferris Buellers and Bill & Teds of the world. The coming-of-age comedy was written by Cameron Crowe (who would go on to write/direct a string of successes, like Jerry Maguire and Say Anything) and directed by Amy Heckerling (Clueless), so you’re in good hands. While Sean Penn’s stoner character at war with his history teacher is perhaps the most memorable p(l)ot of the movie, the main focus is on Stacy and Mark (Jennifer Jason Leigh and Brian Backer), who are trying to find their way romantically with the help of some older students. One of those meandering films that seemingly go everywhere and nowhere at the same time, this 90-minute film is a quick treat. It’s also Nicolas Cage’s film debut!
Watch it on Amazon Prime.
23.*Fight Club (1999)
The first rule of Fight Club may be "Do not talk about Fight Club," but here I am talking about it anyway. The cult classic David Fincher film, based on a Chuck Palahniuk novel, is a must-watch, if only to know all of the references people constantly make to this film. The rules. The soap. Brad Pitt's sweaty abs. This trippy film about a straitlaced man's crisis and descent into insomniac madness has become a favorite among those dissatisfied by consumerism, complacency, and the corporate machine. The film is also filled with endless Easter eggs and hidden references so that even those who have seen it a dozen times will still pick up on something new. And like I said, Brad Pitt's sweaty abs.
Watch it on Amazon Prime.
24.Forgetting Sarah Marshall (2008)
Yeah, yeah, yeah. Jason Segel, Mila Kunis, and Kristen Bell are great in this comedy about a man who goes on vacation to forget his ex-girlfriend, only to find her at the same Hawaiian resort with her new boyfriend. What kicks this gut buster into overdrive, however, is the scene-stealing turns from the supporting cast. This is, of course, the movie that launched Russell Brand (albeit with a rapid meteoric rise and fall) to American stardom as Bell's new rock star boyfriend. But we've also got Paul Rudd's dumb surf instructor, Jonah Hill's pothead waiter, and Bill Hader as the advice-hocking brother. My favorite addition to the vacation, however, are Jack McBrayer and Maria Thayer as the virgin newlyweds experiencing sex for the first time. "If God was a city planner, he would not put a playground next to a sewage system." A classic line.
Watch it now on Amazon Prime.
25.*Get Shorty (1995)
We saw in The Godfather that the mob and the film industry do not always go hand in hand. Occasionally, when the two worlds touch, you end up with a horse head in your bed. In Get Shorty, however, the merger of cinema and "construction" leads to a more pleasant effect. John Travolta's Chili heads from Miami to LA to settle a debt with a B-movie director (Gene Hackman) and somehow manages to find himself as the newest member of a production team. The gangster comedy sends its lead down an increasingly absurd and humorous path as he's tasked with casting an aging scream queen (Rene Russo) and her Oscar-winning ex (Danny DeVito) in the new film. The whole film is like one of Donkey Kong's mine cars, bouncing down a path of messy, chaotic fun — but we're enjoying every single minute of it.
Watch it on Amazon Prime.
26.The Girl With the Dragon Tattoo (2011)
I swear there will be things on this list aside from snowy thrillers, but here’s another one, just in case. Back in the ’00s, Stieg Larsson’s trilogy of Swedish psychological crime thrillers sold like gangbusters and were then adapted into a trio of Swedish-language films starring Noomi Rapace. Fresh off their success, David Fincher (Mank) decided to adapt the books for an American film starring Rooney Mara as the punk cyberhacker Lisbeth Salander and Daniel Craig as journalist Mikael Blomkvist. The unlikely pair team up to investigate the missing person case of a girl who disappeared 40 years earlier. While this Part 1 of the trilogy never received its sequels, it is a harrowing and captivating mystery, and Mara’s Best Actress–nominated performance is worth a watch in and of itself.
Watch it on Amazon Prime.
27.*The Graduate (1967)
If you've ever heard the phrase "Mrs. Robinson" used for an older woman seducing a younger man, this is where the term came from. Anne Bancroft played the OG Mrs. Robinson (in an Oscar-nominated performance, I might add) in this '60s romantic dramedy. A very young Dustin Hoffman is the titular graduate, done with college and adrift in the world, unsure what to do with his life. Then he meets Mrs. Robinson, who has some ideas as to what/whom he should do. The film, directed by the legendary Oscar-winning Mike Nichols, scooped up seven Oscar nominations on its way to becoming a cultural touchstone and launching Hoffman's career. This is also the film we have to thank for the great Simon & Garfunkel song.
Watch it on Amazon Prime.
28.The House Bunny (2008)
What a delightfully bonkers premise for a movie. A Playboy bunny gets kicked out of the Playboy mansion but doesn’t know what to do with herself while living alone, and so decides to be the house mother to a dorky sorority of misfits. Anna Faris gives a career-best performance as the ditzy and earnestly lovable Shelley Darlingson, and you can’t help but root for her, her romance with the nerdy Colin Hanks, and her attempts to empower the Zetas to get out of their shells. The sorority girls are expertly cast — from Emma Stone, in one of her earlier film performances, and WandaVision’s Kat Dennings to American Idol runner-up Katharine McPhee and Cheetah Girl, Cheetah Sister Kiely Williams. It may have a 43% on Rotten Tomatoes, but clearly, film critics in 2008 were just not up to the task of recognizing art.
Watch it on Amazon Prime.
29.In Bruges (2008)
Colin Farrell’s character, Ray, may want nothing to do with Bruges, Belgium, but this film had the opposite effect on me. I have a very intense desire to visit the little town full of cafés and canals, so if you want to be my travel buddy, let me know. Martin McDonagh’s crime comedy follows Ray and Brendan Gleeson’s Ken, both hit men, as they hide out in Bruges until their recent kills blow over. The sleepy exile turns chaotic, however, when Ken is instructed to murder Ray. Ralph Fiennes plays their profanity-prone boss, and the Academy of Motion Picture Arts and Sciences must have liked the curse words because the screenplay was nominated for an Oscar. I will say that this film has left me terrified of bell towers, though, so that’s a potentially negative side effect.
Watch it on Amazon Prime.
30.In Her Shoes (2005)
It’s impossible to have too much Toni Collette, so here’s another great T.C. choice for you, adapted from Jennifer Weiner’s book. In Her Shoes follows a pair of sisters, Rose (Collette) and Maggie (Cameron Diaz), who are polar opposites. Obviously, Rose is the uptight serious one, and Maggie is the alcoholic free spirit. After the two have a falling out because Maggie sleeps with Rose’s boyfriend, Maggie flees to Florida to connect with her estranged grandmother (Oscar winner Shirley MacLaine). A dramedy about sisterhood, motherhood, and understanding those who are different from you, it’s the perfect ratio of laugh-out-loud to tearfully-call-your-sister-and-tell-her-how-much-you-love-her.
Watch it on Amazon Prime.
31.Inside Llewyn Davis (2013)
I would like to begin this section with a direct appeal to Spotify: Dear Spotify executives, please put the entire Inside Llewyn Davis soundtrack on your site. Why do we get only three songs? I know it’s probably got something to do with legal things, but it’s rude nonetheless. Thank you. If, however, you would like to hear the entire soundtrack from this Coen Brothers folk musical, you can watch it on Amazon Prime. Oscar Isaac plays the titular struggling folk singer as he tries to make sense of his life, and sings haunting melodies in the process. My beloved Carey Mulligan and the scandal-shrouded Justin Timberlake also make appearances (although their song isn’t on Spotify). This underappreciated, lyrical film should have been showered with more awards and praise than it was. Sometimes the people just get it wrong.
Watch it on Amazon Prime.
32.Jack and Jill (2011)
I will not be reading the comments for this article, because I KNOW you all are going to rake me over the coals for this one, but this is actually an incredible film. Does it have a 3% on Rotten Tomatoes? Yes. Did it win every single Razzie the year it came out? Yes. But those folks are not watching this film from the perspective that it's a masterpiece of camp. Send this film to the 2019 Met Gala! Adam Sandler (whose recent Hubie Halloween is also a winner) plays both Jack and Jill, fraternal twins, in this truly bonkers affair. It’s stuffed to bursting with product placement (Dunkin' Donuts, anyone?), Sandler is bouncing off the walls as Jill, and the writing often borders on nonsensical. And yet SOMEHOW, Sandler convinced Al Pacino to play himself in this film as the third-billed actor, AND convinced him to fall in love with Jill! Insane. Honestly, I have no idea how this fever dream of a film got made, but I’ve watched it several times, and I will watch it again. (Oh, and the Survivors loved it.)
Watch it on Amazon Prime.
33.Jennifer's Body (2009)
When Jennifer's Body came out over a decade ago, is was panned by (mostly male) critics and marketed largely as the latest film in which to ogle Megan Fox straight off her stint in the Transformers franchise. However, in a post–#MeToo world, and especially after this summer, as society relitigates the way Fox was treated during her rise, this horror comedy has become a feminist cult classic. The film was written by female screenwriter and Oscar winner Diablo Cody, directed by female director Karyn Kusama, stars women, and yet is miraculously not either a romance or about motherhood (try finding films from before 2018 that fit those qualifications). It's also about a (female) succubus who can survive only by killing and eating men (an urge that seems oddly relatable sometimes). Let's get the team on the phone because this is set up nicely for a sequel, and we'd like to see it.
Watch it now on Amazon Prime.
34.The Kids Are All Right (2010)
I'd like to start the coverage of this film by saying that Josh Hutcherson's character is named "Laser," which is the kind of chaotic naming of fictional characters you've got to get behind. But that is neither here nor there. This Best Picture–nominated family drama about a pair of lesbians raising two teenagers is exquisite and a massive push for representation, since same-sex couples with kids are still rarely seen in the media. The film focuses on the family once Laser brings his sperm donor (played by Mark Ruffalo) into the lives of his mothers (played by Annette Bening and Julianne Moore in award-winning turns). Small and intimate in some ways and yet bombastic in the stories it is trying to tell and the force of the performances, The Kids Are All Right is a necessary watch.
Watch it now on Amazon Prime.
35.Knives Out (2019)
You’ve got to love a classic whodunit, especially with an ensemble cast of the caliber of this one. Rian Johnson’s mystery (so well written, its screenplay landed an Oscar nom) focuses on the death of Harlan Thrombey, a famous novelist, and the family desperate to scoop up his inheritance. I know that listing actors is boring, but just go with me here. We’ve got James Bond himself, Daniel Craig, and his future Bond girl/Ben Affleck’s former coffee-walks partner, Ana de Armas. America’s Ass Chris Evans is there in a beautiful cable-knit sweater. Halloween badass/yogurt guru Jamie Lee Curtis is a suspect, as is two-time Oscar nominee Michael Shannon. Lime enthusiast Dakota Johnson’s dad, Don, is here, and so is perhaps the world's greatest living actor, Toni Collette. LaKeith Stanfield is here without his straw hat from Get Out, and so is 13 Reasons Why’s ghostly Katherine Langford. And just as a final flex, the casting director secured Pennywise’s favorite victim, Jaeden Martell, and the legendary Christopher Plummer, may he rest in peace. Like, really. It’s an all-star lineup, and there's something similar planned for the sequel.
Watch it on Amazon Prime.
36.The Last Black Man in San Francisco (2019)
In case you haven’t checked the news in the last decade, San Francisco is in the midst of (or perhaps ending) a MASSIVE wave of gentrification, thanks to the explosion of Silicon Valley, and the area’s been flooded by affluent white tech moguls. As a result, streets previously occupied by Black families are now almost entirely white. Thus is the story of Jimmie Fails, who wrote this film based partly on his life. He plays a man set on reclaiming his childhood Victorian home from a gentrified neighborhood, lovingly taking care of the beautiful house behind its owners’ backs. Hauntingly poignant and tragically melancholy, the film, an indictment of gentrification, also engages with the pains of growing up, of change, and of having to say goodbye.
Watch it on Amazon Prime.
37.*The Life Aquatic With Steve Zissou (2004)
With the wide release of The French Dispatch rapidly approaching, perhaps now is a good time to revisit some of Wes Anderson's older titles, including this maritime comedy starring Bill Murray. Murray plays Zissou, a Jacques Cousteau–like figure intent on getting revenge on the jaguar shark for killing his former partner. In classic Wes Anderson fashion, the film is beautifully shot in brightly colored, immaculately constructed, symmetrical frames. Also in classic Wes Anderson fashion, the film stars a sprawling cast of A-listers, including Anderson regulars Owen Wilson, Willem Dafoe, Anjelica Huston, and Jeff Goldblum. Beware, however — watching Steve Zissou could give you the urge to buy a red beanie.
Watch it on Amazon Prime.
38.The Lighthouse (2019)
Robert Eggers’ follow-up to The Witch (where we all learned to live deliciously) is a claustrophobic psychological nightmare and anything but delicious (unless dead seagulls and farting whet your appetite). Shot in black-and-white with a nearly square aspect ratio, the film resembles an 1800s home video as it tracks Willem Dafoe and Robert Pattinson’s characters to a rocky island lighthouse. Fueled by alcohol and cut off from society, the pair descend into a salty, windswept madness. This is certainly not for everyone, but those of you with a strong constitution and love of psychological horror will find this a riveting exploration of the untethered mind. Watch it while we anxiously await The Northman, Eggers’ next film.
Watch it on Amazon Prime.
39.Manchester by the Sea (2016)
Manchester by the Sea is a beautiful, if disastrously depressing film written and directed by Kenneth Lonergan. Michelle Williams and Casey Affleck both give incredible performances (even if Casey’s more recent controversies have detracted from his star power). But what I’d like to discuss is the birth of Lucas Hedges into the American consciousness. Hedges plays Patrick, a 16-year-old with a THICK Boston accent, who goes to live with his depressed uncle (Affleck) after the death of his father. His performance is so strong that it nabbed him a rare young male Oscar nomination and launched him into lead roles in subsequent films like Ben Is Back and Boy Erased. He would also go on to become an A24 darling in films like Lady Bird and Waves. Just as I couldn’t stop looking at this recent photo of him, I was transfixed by his presence here and have loved watching his journey to stardom.
Watch it on Amazon Prime.
40.Midsommar (2019)
Where do I even begin to describe my love for this horror film? Directed by Ari Aster (whose Hereditary is somehow even better), Midsommar follows a group of friends who travel to Sweden for a folk festival. Only, instead of a normal village, there's something menacing and mysterious at play. Aster does the seemingly impossible job of making a field in broad daylight scarier than the dark, and the dread he creates in these scenes is palpable. At the center of this detailed masterpiece is Florence Pugh’s breakout performance as a grieving woman, whose family just died, on vacation with a boyfriend. It’s terrifying. It’s beautiful. It’s oddly cathartic. Although I will never forgive it for teaching me what a blood eagle is.
Watch it on Amazon Prime.
41.*My Name Is Pauli Murray (2021)
I am ashamed to say that prior to watching this documentary, I had no idea who Pauli Murray was. If you, too, have never heard of this fascinating, groundbreaking, trailblazing individual, then you need to hustle right on over to Amazon and give this a watch. A civil rights activist who refused to give up her seat on the bus before Rosa Parks. An African American lawyer whose work paved the way for Ruth Bader Ginsburg's landmark cases on sexism. A queer intellectual who sought to understand gender and sexuality in a time before modern labels. Murray is an icon we should be learning about in school, so if you're a schoolteacher and you're reading this article, wheel that TV into the classroom and press play.
Watch it on Amazon Prime.
42.One Night in Miami (2020)
In 1964, famed African American civil rights activist Malcolm X, boxer Muhammad Ali, football star Jim Brown, and singer Sam Cooke all spent an evening together in a hotel room in Miami. That historic meeting serves as the basis for this film, directed by Regina King (a previously Oscar-winning actor herself) and adapted by Kemp Powers, who also wrote the play and Pixar's Soul (big year for him!). Focused on the relationships between these four great men, the film creates fictional dialogue that aims to unpack race, privilege, and the responsibility that comes with fame. Hamilton’s Leslie Odom Jr. plays Cooke (a performance for which he was Oscar-nominated), but it's Kingsley Ben-Adir’s take on Malcolm X that is most captivating. Never has such a long stay in a hotel room been so interesting.
Watch it on Amazon Prime.
43.Pride (2014)
I LOVE to promote a good LGBTQ film, and this funny little historical British dramedy is a fantastic one. Back in 1984, during a British miners' strike, gay activist Mark Ashton (Ben Schnetzer) realized that the police were too busy focusing on the miners to focus on their usual harassment of the gay community, and so he started Lesbians and Gays Support the Miners to help a fellow group of oppressed folks. It’s this fight by the LGBTQ community on behalf of the labor class that serves as the plot here. Hot priest Andrew Scott is here, along with 1917’s George MacKay and Professor Umbridge, aka Imelda Staunton. The film is charming and uplifting and shows you how underdogs helping underdogs can do a lot of good for everyone.
Watch it on Amazon Prime.
44.*Prometheus (2012)
Before the xenomorphs were chasing Sigourney Weaver & Co. around the Nostromo, they were wreaking havoc on the crew of Prometheus in this prequel to Alien. Noomi Rapace (pre–lamb mom days) and Michael Fassbender lead this new (although, technically speaking, older) cohort as they search for human ancestors in space. What they find, however, is a violent alien life form that ends up impregnating Rapace's Shaw, leading to a disgusting birthing scene and a baby alien ready to cause trouble for countless future generations. Moral of the story: Don't mess with aliens.
Watch it on Amazon Prime.
45.*Raising Arizona (1987)
There's nothing I love more than a ridiculous crime film from the Coen Brothers, and Raising Arizona is certainly ridiculous. Holly Hunter plays a cop who falls in love with a convict played by Nicolas Cage (I mean, that casting alone is gold). The two can't have a kid, so they decide to steal a quintuplet from a furniture tycoon. Then a competing set of criminals steal the baby from Hunter and Cage — pure lunacy in the best possible way. The crime comedy is a bit lighter than the Coens' usual fare, but the ingenuity is all there, and you've got supporting performances from Frances McDormand and John Goodman to boot. If The Tragedy of Macbeth strikes you as a bit too somber, this might be the Coen film for you.
Watch it on Amazon Prime.
46.Rear Window (1954)
We’ve had a lot of “I saw a murder out my window” movies recently, from The Woman in the Window to The Girl on the Train, but this Alfred Hitchcock classic is the original. Jimmy Stewart’s Jeff is laid up in a Greenwich Village apartment with a broken leg and has nothing to do to amuse himself but look out his window. When he believes he’s seen one of his neighbors murder his wife, however, Jeff and his girlfriend, played by Grace Kelly, set out to investigate. What starts as curiosity quickly leads them in over their head. The film is a staple in the American canon and is CONSTANTLY referred to or riffed on, so really, you owe it to yourself to see the original.
Watch it on Amazon Prime.
47.Revolutionary Road (2008)
Titanic stars Leonardo DiCaprio and Kate Winslet, forever forged together through the press surrounding that mega-blockbuster, have famously remained friends. So it was not particularly surprising, then, when the two reunited to costar in this romantic drama from Sam Mendes (1917). The pair play the Wheelers, a '50s couple living what is seemingly the perfect suburban Connecticut life, only to be suffocated under malaise, boredom, and the breakdown of their marriage. As with Titanic, this is a romantic tragedy, and also as with Titanic, Kathy Bates is there. It’s not a happy movie, but it’s fascinating to watch these two great actors do their thing. If only there were a Celine Dion song thrown in.
Watch it on Amazon Prime.
48.Romeo + Juliet (1996)
Thank god for Baz Luhrmann, because without this version of Shakespeare's Romeo and Juliet, high school English classes everywhere would be forced to watch much stuffier renditions of the famed romantic tragedy. Luhrmann took the play, reset it in a glitzy, fictionalized Miami, cast teenage heartthrobs Leonardo DiCaprio and Claire Danes as the leads, and injected the whole thing with a level of eye-popping fun that Marlon Brando and Kenneth Branagh could never. The scene where Rom and Julie lock eyes through a fish tank? Genius. The whole pool encounter? Swoonworthy. And the SOUNDTRACK. DO NOT EVEN GET ME STARTED ON THAT SOUNDTRACK, BABY. Obviously, one of the best in film history. "Young Hearts Run Free" by Kym Mazelle is the boppiest of bops. Makes me want to put on drag and dance down a staircase.
Watch it now on Amazon Prime.
49.*Rugrats Go Wild (2003)
If there are two iconic badass Nickelodeon women we should all aspire to be, they are the megalomaniacal toddler Angelica Pickles from The Rugrats and the too-cool-for-school, blasé Debbi Thornberry from The Wild Thornberrys. The beauty of this crossover animated film is that the two sassy villains get to go on a trip together. Finally, instead of stupid babies and gorillas, these women get to interact with someone on their own intellectual level, and there is magic to behold. ALSO, this has nothing to do with watching this on Amazon, because sadly, the tech is not here yet, but when I saw this movie in theaters, I watched it with an Odorama scratch-and-sniff card from Burger King, so I got to smell the action. Never has there been a more magical theatergoing experience.
Watch it on Amazon Prime.
50.Shooter (2007)
Apparently, it is possible to shoot a gun and hit a target from a mile away. A MILE! And Mark Wahlberg’s character in Shooter has that ability. He’s that good. And because of this fact, the bad guys are both very smart and very dumb. Smart because he’s an easy scapegoat for a presidential assassination attempt. But when he escapes arrest and starts searching for revenge, he is an enemy you REALLY don’t want to have. Shooter is certainly not an Oscar nominee, but it is a fun action movie to watch while munching on popcorn. Who doesn’t love a good revenge plotline? And if you sprinkle in a little government conspiracy and a few great action sequences, I’m fully there. It’s also a good reminder to keep your curtains closed.
Watch it on Amazon Prime.
51.Short Term 12 (2013)
I don’t know what was happening on the set of Short Term 12, but someone had a rabbit's foot or made a deal with the Illuminati, because truly, everyone in this tiny indie drama has gone on to have their careers BLOW UP! There’s Captain Marvel herself, Brie Larson. There’s Booksmart’s scene-stealer Kaitlyn Dever. There’s Best Actor/Freddie Mercury impersonator Rami Malek. There’s Brooklyn Nine-Nine star Stephanie Beatriz. And of course, there is the very recent Oscar nominee for Judas and the Black Messiah, LaKeith Stanfield. This film, which focuses on a group home for troubled teenagers, is funny, sad, and heartwarming in its own right, but watching all your current faves’ younger selves is a trip.
Watch it on Amazon Prime.
52.Sideways (2004)
Some would say (and by “some,” I mean "I") that Paul Giamatti’s best work is in Big Fat Liar. Far more would say he shines in this Best Picture nominee. The dramedy follows Giamatti’s depressed, unsuccessful writer, Miles, and his friend, has-been soap opera star Jack (Thomas Haden Church in an Oscar-nominated role), as the pair take a trip to wine country before Jack’s wedding. What follows is a chaotic, rambling film that is somehow cheerful, depressing, inspiring, and hilarious all in one swoop. It’s a rumination on aging and friendship that snatched five Oscar nominations and took home the trophy for the screenplay. And since Big Fat Liar is not streaming on Amazon, this is your next-best bet.
Watch it on Amazon Prime.
53.The Social Network (2010)
Where does one even begin when trying to nail down the greatness of the film? Perhaps it's in the Aaron Sorkin script that so aptly gives life to the chaos of Facebook's creation. Perhaps it's in Jesse Eisenberg's star-making turn as founder Mark Zuckerberg, in which he chews up and spits out Sorkin's dialogue as few others have been able to. Perhaps it's in the pitch-perfect casting of Andrew Garfield as the sympathetic elitist Eduardo Saverin, or Justin Timberlake as the slimy Sean Parker. Perhaps it's in David Fincher's masterful directing or in the haunting, soft, Oscar-winning score. While each of these aspects is masterful, however, I'm going to give the edge to Rooney Mara's brief performance in the film's opening scene, where she dumps Eisenberg. It launches the film to a high-octane propulsion that it will maintain until the credits, and perfectly frames how even something as massive as Facebook can really just be a means of compensating for a bruised ego.
Watch it now on Amazon Prime.
54.Sound of Metal (2019)
One of this year’s freshly minted Best Picture nominees, Sound of Metal follows Ruben, a heavy metal drummer who comes to the (at first) horrifying realization that he is losing his hearing. The indie drama, which continued to pick up more steam and accolades through the awards season, stars Riz Ahmed in the lead as he mourns his hearing and struggles to find ways to cope. Both he and Paul Raci, who plays the deaf leader of a shelter for recovering addicts, landed Oscar noms for their performances, and Olivia Cooke, who plays Ruben’s girlfriend, rightfully should have received one as well. This fascinating film also substantiates my mom’s claim that "you are going to lose your hearing from turning the radio up too loud."
Watch it on Amazon Prime.
55.The Souvenir (2019)
With The Souvenir Part II fresh off its well-received premiere at the Cannes Film Festival and headed to theaters in the fall, there is no time like the present to catch up on the first installment of Joanna Hogg’s autobiographical film duology. The Souvenir Part I stars Honor Swinton Byrne (the daughter of Tilda Swinton, who also appears in the film) playing a version of Hogg through her encounters at film school. Byrne’s Julie meets Anthony (Tom Burke), and the two have a whirlwind romance that is cut short when some details of Anthony’s unsavory past float to the surface. The quiet, lyrical film is a sad little treat (like so many A24 titles), and the performances shine. I can’t wait to see round two.
Watch it on Amazon Prime.
56.Stop Making Sense (1984)
As someone with particularly bad musical taste, I will take this moment to admit that I had no idea who the Talking Heads were until this summer, when I watched David Byrne’s American Utopia, a filmed version of the Broadway performance. Byrne, for the uninformed, was the lead singer of a new wave band called the Talking Heads (the one song I knew by them was used in the trailer for the horrid Matt Damon film Downsizing). American Utopia, however, gave me an appreciation for the Talking Heads, and so I naturally stumbled upon Stop Making Sense, which is a filmed version of their live performances at the Pantages Theater in 1983. It is an exquisite concert film. The music is wonderful. The concert is theatrical. And the whole thing jumps off the screen in a way that concert videos don’t often manage to do. So everyone follow my lead and become a Talking Heads fan. Better three decades late than never.
Watch it on Amazon Prime.
57.Sunset Boulevard (1950)
We start with a mansion on Sunset Boulevard. And oh look, there is a body floating facedown in the swimming pool. Whose body is it? How did it get there? You’ll have to watch to find out. The black-and-white Hollywood classic tracks the events leading up to the mysterious death, as William Holden plays a young screenwriter who is slowly sucked into the web of the reclusive former silent-film star Norma Desmond (Gloria Swanson). The iconic film, which gave us lines like “Mr. DeMille, I’m ready for my close-up,” was nominated for 11 Oscars and holds an ironclad spot in the film canon. A perfect film, it feels startlingly modern even as it is a ’50s noir, and it packs just as much punch today as it did at its release.
Watch it on Amazon Prime.
58.*Taken (2008)
The influence of Taken on our cinematic landscape cannot be overstated. In 2008, when it was released, the whole thing was seen as an anomaly. An action film starring a nearly 60-year-old actor most notable for dramas like Schindler's List? Who would go and see that? Well, apparently, a lot of people (and a lot of dads). The film was so successful, it launched a whole genre of old-man action films, including a dozen for Liam Neeson himself. Now Sylvester Stallone, Bruce Willis, and Mel Gibson are all talking up their "very particular sets of skills." Despite all of the flawed follow-ups, however, Taken still stands as the exemplar of the genre, and far be it from me to pass up an evening of Neeson taking out 50 baddies, all half his age.
Watch it on Amazon Prime.
59.*Thank You for Smoking (2006)
Oh, the joys of watching the mental gymnastics involved in marketing cigarettes as a "good life decision." And yet there is a whole multimillion-dollar industry dedicated to enticing people to inhale fumes they know could give them cancer. Thus is the premise of this satirical comedy in which Aaron Eckhart works as the chief spokesperson for the tobacco industry. The darkly funny film follows Eckhart as he employs all manner of spin tactics to assure the public that smoking isn't that bad, all while trying to maintain his status as a good guy in the eyes of his family. I 10/10 wouldn't recommend smoking, but I would recommend this film.
Watch it on Amazon Prime.
60.Time (2020)
Rarely do we get a documentary as raw and moving as Time. The film follows Fox Rich, using over 25 years’ worth of home videos as she fights tirelessly for her husband, Rob, who is serving time in prison for his participation in an armed bank robbery, to be granted clemency. What filmmaker Garrett Bradley thought would be a short film turned into a feature when Fox handed her over 100 hours' worth of home video footage taken while her husband was in prison. Bradley then took the home videos and her own footage, converted it all to stunning black-and-white, and built the moving, 81-minute-long final product. The documentary, which was nominated for an Oscar, vividly shows the flaws of the criminal justice system and how that can deeply affect the families of those struggling through it. It’s a beautiful statement as to what can be accomplished if you try hard enough, and how important it is to have someone tirelessly in your corner.
Watch it on Amazon Prime.
61.The Tomorrow War (2021)
A recent 2021 release, this Chris Pratt sci-fi film is set in a world in which aliens overrun the planet in 30 years. The future, therefore, is drafting humans from the present to time-travel to the future to fight off the aliens in order to save humanity. Pratt, playing a former Green Beret, is drafted alongside a ragtag crew including Sam Richardson (Veep) and Mary Lynn Rajskub (aka Gail the Snail from It's Always Sunny in Philadelphia). While the time-travel logistics are a bit murky, the action sequences (especially on a giant, oil rig–style military base) are incredible, and the monsters will give you nightmares.
Watch it on Amazon Prime.
62.Traffic (2000)
First, I'd like to say that this movie is not Crash, a distinction that took me many years to realize, as they are both one-word, car-related titles with ensemble casts from the early aughts that did well at the Oscars. But while Crash is a very problematic film about racism, a car crash, and Sandra Bullock just being angry and not knowing why, Traffic is a Steven Soderbergh film about the illegal drug trade. The ensemble cast features Don Cheadle (who is trying to forget he was in Space Jam 2), Benicio Del Toro (who won an Oscar for the role), Michael Douglas and Catherine Zeta-Jones (who were dating at the time and are still together), and not–Tad Hamilton Topher Grace. The way the storylines tie together perfectly is a testament to the Oscar-winning screenplay, and the film is as suspenseful and riveting as it is well-done. Should it have beat Gladiator for the Oscar? Probably.
Watch it now on Amazon Prime.
63.Vertigo (1958)
Alfred Hitchcock is a master of the psychological thriller, and nowhere is that made more apparent than in Vertigo. Starring Jimmy Stewart, the film focuses on a former police officer who was pulled from the line of duty after a rooftop chase leads him to develop a fear of heights as well as vertigo. In retirement, however, he is called upon by a friend from college to investigate his wife (played by Kim Novak), who is behaving oddly. What follows is a twisty cat-and-mouse game of identity and fear, culminating in a bell tower scene that is one for the ages. And don’t let its age fool you — this movie is just as suspenseful as anything being made today. Don’t trust me? Give it a try.
Watch it on Amazon Prime.
64.*Wanderlust (2012)
By most accounts, this movie barely exists. When it came out, it made virtually no money and was unceremoniously swept out of theaters after just six weeks with average ratings from critics. That, however, is unfair because this is a funny movie, y'all, with an unimpeachable cast. The premise: Jennifer Aniston and Paul Rudd accidentally find themselves on a hippie commune in Georgia after their big-shot New York City dreams are killed in the recession. And so now they get to spend an entire film on a farm with kooky individuals played by Jordan Peele, Justin Theroux, Malin Akerman, Alan Alda, and, of course, the brilliant Kathryn Hahn. Yet no one has ever heard of this movie, for some reason. Be the hero to your friend group. Go watch this, tell everyone you know about it, and then bask in their praise for having found this hidden gem.
Watch it now on Amazon Prime.
* Denotes title that has been newly added to Amazon Prime for October.
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