Watch Haley Joel Osment Grow Up on the Red Carpet Through the Years, in Photos

Ahead of the former child star's appearance in Zo? Kravitz's 'Blink Twice,' here's a look back at his numerous red carpet appearances over the years

Haley Joel Osment's career in Hollywood dates back 30 years!

The actor, 36, became a household name in 1999 after starring in M. Night Shyamalan's The Sixth Sense and from there secured several roles on film and TV, and in 2008 made his Broadway debut in American Buffalo. This summer, he is set to star in the Zo? Kravitz-directed Blink Twice  alongside Channing Tatum and Alia Shawkat.

From hitting awards shows in a pint-sized tux to sporting a full beard and flowing hair, take a look back at Osment's red carpet appearances over the last three decades.

Adorable Pair

In 1997, Haley Joel Osment hit the red carpet with a furry friend named Sparky at the Genesis Awards in L.A.

Denim Days

Months after the young actor became a household name with his performance in The Sixth Sense, Haley Joel Osment looked adorable in a very '90s denim look for the 1999 premiere of Bicentennial Man.

Dynamic Duo

Haley Joel Osment reunited with his The Sixth Sense director M. Night Shyamalan for the People's Choice Awards in 2000. The young actor looked sharp for the occasion, sporting a full-on tuxedo.

Supporting Sister

Haley Joel Osment supported his little sister, actress Emily Osment, at the premiere of her 2002 movie, Spy Kids 2: The Island of Lost Dreams. The two looked extra cute with their arms wrapped around each other, both sporting sunglasses.

Sweet Reunion

Haley Joel Osment stepped out for the 2006 Little Miss Sunshine premiere, which starred his onscreen mom from The Sixth Sense, Toni Collette.

Stage Star

In 2008, not long after the actor's 20th birthday, Haley Joel Osment hit the red carpet to celebrate his Broadway debut at the opening night of American Buffalo.

Clean Cut

The actor was clean shaven for the 2013 Anchorman 2: The Legend Continues premiere in New York City.

Shades On

Haley Joel Osment took a note from his younger self's style when he pulled out a pair of round sunglasses with dark lenses at the L.A. premiere of Entourage in 2015.

New Look

The star rocked a full beard for the Preacher season 2 premiere in 2017.

Sibling Bonding

The Osment siblings were dressed to the nines for the Screen Actors Guild Awards in 2022.

Pop of Color

In 2023, Haley Joel Osment sported an all-black look, topped off with a red skinny tie, for the premiere of Somebody I Used to Know, which he starred in with Alison Brie and Jay Ellis.

A Good Cause

Weeks before he'll hit the red carpet for the premiere of Blink Twice, Haley Joel Osment made time for the Children's Charity of Southern CA Poker and Casino Night on July 24, 2024.

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