Peter Segal remembers how 'happy' a sober Chris Farley was making 'Tommy Boy': 'It was a really nice time'

As Tommy Boy turns 30, director Peter Segal feels a “mix of emotions” about the odd-couple buddy comedy starring Chris Farley and David Spade.

“It warms my heart and sometimes makes me sad,” Segal tells Yahoo Entertainment about seeing Farley, who died in 1997 at age 33, on the big screen again. “It brings me right back to those days.”

Tommy Boy — which is getting a new 4K ultrahigh definition release from Paramount in honor of its anniversary — was the second film Segal directed, after 1994’s Naked Gun 33?: The Final Insult. It was also “definitely the hardest production I've done” out of his 12 movies.

The film, produced by Saturday Night Live’s Lorne Michaels, had an incomplete script — just 66 pages — that was rewritten on the fly throughout production. They ran behind schedule, which meant Farley and Spade had to pull double-duty filming, in Toronto and flying back to New York to shoot SNL.

“When I look back … it looks so nice and sweet and innocent on the big screen, but it wasn't getting there,” he said. “I think it was the most chaotic [film] that I worked on and I hope I never have a process that difficult again. I don't recommend it.”

Segal added, “It's a mix of emotions looking at it now.”

Segal, who went on to direct The Longest Yard, 50 First Dates and Anger Management, had previously worked on a Farley comedy special and was excited to helm his first leading film role — about lovable but dim-witted nepo baby Tommy Callahan III, who inherits his dad’s auto parts business in Sandusky, Ohio — amid his breakout success from SNL.

Farley had already been dealing with substance use disorder at that point but was sober while making this film. Segal remembers how happy Farley was while filming and how the star’s biggest vice at the time was drinking 27 coffees a day on set.

“I was fortunate to have worked with Chris both when he was not clean and sober and then during this movie where he was,” Segal said. “He replaced his other substances with caffeine. So, yeah, he drank a lot of coffee. Too much. But that was his process. Seeing how happy [Farley] was during filming, even though it was a hard shoot, it was a really nice time. So I was like: Fine by me if you want your 28th cup. All good.”

While the film is a comedy — with the still hilarious sparring between Tommy and his father’s overlooked assistant Richard Hayden (Spade) — it also showed Farley’s range. The film ends with him in a sailboat, talking to the spirit of his late dad. Segal said that scene, like the rest of the film, wasn’t easy either.

The film “didn't have an ending," Segal said, and it was a last-minute suggestion by Stripes screenwriter Len Blum to shoot the final scene back at the lake. They had to scramble to get back to that set and hope for calm winds that day, and they shot the scene.

“Chris was on his way home and there was an accident with the film and it got ruined,” Segal said. “We had to have Chris make a U-turn, come back and do that emotional scene a second time,” adding to the "arduous process” of completing the film.

Bo Derek played Farley’s deceitful stepmother in the film and Rob Lowe his conniving stepbrother. While Lowe played the role to a tee, it was almost a very different actor in that role: Matthew McConaughey.

“Matthew had just done [1993’s] Dazed and Confused, so he was very young in his career,” Segal said. “He's awesome — it's just as casting goes, you’re looking for certain things and Rob seemed to fit that. Now, you can almost never imagine anybody but Rob in the role. But that's usually how it goes when you realize how close someone else was to that role.”

Meanwhile, Derek and Lowe, who turned out to be a money-hungry couple in the film, made for a fetching pair — even with Lowe’s character getting beaten up throughout the movie.

“Let me just tell you that when you go to dinner with Rob Lowe and Bo Derek, I could be on fire and no one would notice me,” Segal said. “But we struggled through that.”

Paramount’s 30th Anniversary Tommy Boy 4K UHD is now available.