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

Mar. 15, 2025

Haley Joel Osment in 1999, 2006 and 2024.Photo:Ron Galella, Ltd./Ron Galella Collection/Getty; E. Charbonneau/WireImage; Unique Nicole/Getty

Ron Galella, Ltd./Ron Galella Collection/Getty; E. Charbonneau/WireImage; Unique Nicole/Getty

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

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.

01of 12Adorable PairHaley Joel Osment with Sparky the dog in 1997.Barry King/LiaisonIn 1997, Haley Joel Osment hit the red carpet with a furry friend named Sparky at the Genesis Awards in L.A.02of 12Denim DaysHaley Joel Osment in 1999.Ron Galella, Ltd./Ron Galella Collection/GettyMonths after the young actor became a household name with his performance inThe Sixth Sense, Haley Joel Osment looked adorable in a very ’90s denim look for the 1999 premiere ofBicentennial Man.03of 12Dynamic DuoM. Night Shyamalan and Haley Joel Osment in 2000.Ron Galella, Ltd./Ron Galella Collection/GettyHaley Joel Osment reunited with hisThe Sixth Sensedirector M. Night Shyamalan for the People’s Choice Awards in 2000. The young actor looked sharp for the occasion, sporting a full-on tuxedo.04of 12Supporting SisterEmily Osment and Haley Joel Osment in 2002.Gregg DeGuire/WireImageHaley Joel Osment supported his little sister, actressEmily 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.05of 12Sweet ReunionHaley Joel Osment in 2006.E. Charbonneau/WireImageHaley Joel Osment stepped out for the 2006Little Miss Sunshinepremiere, which starred his onscreen mom fromThe Sixth Sense,Toni Collette.06of 12Stage StarHaley Joel Osment in 2008.JONATHON ZIEGLER/Patrick McMullan/GettyIn 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 ofAmerican Buffalo.07of 12Clean CutHaley Joel Osment in 2013.Cindy Ord/GettyThe actor was clean shaven for the 2013Anchorman 2: The Legend Continuespremiere in New York City.08of 12Shades OnHaley Joel Osment in 2015.Eric Charbonneau/GettyHaley 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 ofEntouragein 2015.09of 12New LookHaley Joel Osment in 2017.Jesse Grant/GettyThe star rocked a full beard for thePreacherseason 2 premiere in 2017.10of 12Sibling BondingHaley Joel Osment and Emily Osment in 2022.Frazer Harrison/GettyThe Osment siblings were dressed to the nines for the Screen Actors Guild Awards in 2022.11of 12Pop of ColorHaley Joel Osment in 2023.Steve Granitz/FilmMagicIn 2023, Haley Joel Osment sported an all-black look, topped off with a red skinny tie, for the premiere ofSomebody I Used to Know,which he starred in with Alison Brie and Jay Ellis.12of 12A Good CauseHaley Joel Osment in 2024.Unique Nicole/GettyWeeks before he’ll hit the red carpet for the premiere ofBlink Twice, Haley Joel Osment made time for the Children’s Charity of Southern CA Poker and Casino Night on July 24, 2024.

01of 12Adorable PairHaley Joel Osment with Sparky the dog in 1997.Barry King/LiaisonIn 1997, Haley Joel Osment hit the red carpet with a furry friend named Sparky at the Genesis Awards in L.A.

01of 12

Adorable Pair

Haley Joel Osment with Sparky the dog in 1997.Barry King/Liaison

Actor Haley Joel Osment pets Sparky the dog at the Genesis Awards April 5, 1997 in Los Angeles, CA. The Genesis Award is presented by the Ark Trust to honor individuals in the major media and artistic community who have successfully communicated animal-rights issues.

Barry King/Liaison

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

02of 12Denim DaysHaley Joel Osment in 1999.Ron Galella, Ltd./Ron Galella Collection/GettyMonths after the young actor became a household name with his performance inThe Sixth Sense, Haley Joel Osment looked adorable in a very ’90s denim look for the 1999 premiere ofBicentennial Man.

02of 12

Denim Days

Haley Joel Osment in 1999.Ron Galella, Ltd./Ron Galella Collection/Getty

Actor Haley Joel Osment attends the “Bicentennial Man” Hollywood Premiere on December 13, 1999 at the El Capitan Theatre in Hollywood, California

Ron Galella, Ltd./Ron Galella Collection/Getty

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

03of 12Dynamic DuoM. Night Shyamalan and Haley Joel Osment in 2000.Ron Galella, Ltd./Ron Galella Collection/GettyHaley Joel Osment reunited with hisThe Sixth Sensedirector M. Night Shyamalan for the People’s Choice Awards in 2000. The young actor looked sharp for the occasion, sporting a full-on tuxedo.

03of 12

Dynamic Duo

M. Night Shyamalan and Haley Joel Osment in 2000.Ron Galella, Ltd./Ron Galella Collection/Getty

Director M. Night Shyamalan and actor Haley Joel Osment attend the 26th Annual People’s Choice Awards on January 9, 2000 at the Pasadena Civic Auditorium in Pasadena, California

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

04of 12Supporting SisterEmily Osment and Haley Joel Osment in 2002.Gregg DeGuire/WireImageHaley Joel Osment supported his little sister, actressEmily 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.

04of 12

Supporting Sister

Emily Osment and Haley Joel Osment in 2002.Gregg DeGuire/WireImage

Emily Osment & Haley Joel Osment during “Spy Kids 2: The Island Of Lost Dreams” Premiere at Grauman’s Chinese Theatre in Hollywood, California, United States

Gregg DeGuire/WireImage

Haley Joel Osment supported his little sister, actressEmily 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.

05of 12Sweet ReunionHaley Joel Osment in 2006.E. Charbonneau/WireImageHaley Joel Osment stepped out for the 2006Little Miss Sunshinepremiere, which starred his onscreen mom fromThe Sixth Sense,Toni Collette.

05of 12

Sweet Reunion

Haley Joel Osment in 2006.E. Charbonneau/WireImage

Haley Joel Osment during Fox Searchlight Pictures Premiere of “Little Miss Sunshine” at the Closing Night Celebration of The Los Angeles Film Festival at Wadsworth Theater in Brentwood, CA, United States.

E. Charbonneau/WireImage

Haley Joel Osment stepped out for the 2006Little Miss Sunshinepremiere, which starred his onscreen mom fromThe Sixth Sense,Toni Collette.

06of 12Stage StarHaley Joel Osment in 2008.JONATHON ZIEGLER/Patrick McMullan/GettyIn 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 ofAmerican Buffalo.

06of 12

Stage Star

Haley Joel Osment in 2008.JONATHON ZIEGLER/Patrick McMullan/Getty

Haley Joel Osment attends Opening Night of AMERICAN BUFFALO Party Arrivals at 230 Fifth Avenue on November 17, 2008 in New York City

JONATHON ZIEGLER/Patrick McMullan/Getty

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 ofAmerican Buffalo.

07of 12Clean CutHaley Joel Osment in 2013.Cindy Ord/GettyThe actor was clean shaven for the 2013Anchorman 2: The Legend Continuespremiere in New York City.

07of 12

Clean Cut

Haley Joel Osment in 2013.Cindy Ord/Getty

Actor Haley Joel Osment attends the Anchorman 2: The Legend Continues Premiere, Sponsored by Buffalo David Bitton on December 15, 2013 in New York City

Cindy Ord/Getty

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

08of 12Shades OnHaley Joel Osment in 2015.Eric Charbonneau/GettyHaley 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 ofEntouragein 2015.

08of 12

Shades On

Haley Joel Osment in 2015.Eric Charbonneau/Getty

Haley Joel Osment seen at Warner Bros. Premiere of “Entourage” held at Regency Village Theatre on Monday, June 1, 2015, in Westwood, Calif.

Eric Charbonneau/Getty

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 ofEntouragein 2015.

09of 12New LookHaley Joel Osment in 2017.Jesse Grant/GettyThe star rocked a full beard for thePreacherseason 2 premiere in 2017.

09of 12

New Look

Haley Joel Osment in 2017.Jesse Grant/Getty

Actor Haley Joel Osment attends AMC’s “Preacher” Season 2 Premiere at the Theater at the Ace Hotel on June 20, 2017 in Los Angeles, California

Jesse Grant/Getty

The star rocked a full beard for thePreacherseason 2 premiere in 2017.

10of 12Sibling BondingHaley Joel Osment and Emily Osment in 2022.Frazer Harrison/GettyThe Osment siblings were dressed to the nines for the Screen Actors Guild Awards in 2022.

10of 12

Sibling Bonding

Haley Joel Osment and Emily Osment in 2022.Frazer Harrison/Getty

Haley Joel Osment and Emily Osment attend the 28th Annual Screen Actors Guild Awards at Barker Hangar on February 27, 2022 in Santa Monica, California

Frazer Harrison/Getty

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

11of 12Pop of ColorHaley Joel Osment in 2023.Steve Granitz/FilmMagicIn 2023, Haley Joel Osment sported an all-black look, topped off with a red skinny tie, for the premiere ofSomebody I Used to Know,which he starred in with Alison Brie and Jay Ellis.

11of 12

Pop of Color

Haley Joel Osment in 2023.Steve Granitz/FilmMagic

Haley Joel Osment arrives at the Los Angeles Premiere Of Prime Video’s “Somebody I Used To Know” at Culver Theater on February 01, 2023 in Culver City, California

Steve Granitz/FilmMagic

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

12of 12A Good CauseHaley Joel Osment in 2024.Unique Nicole/GettyWeeks before he’ll hit the red carpet for the premiere ofBlink Twice, Haley Joel Osment made time for the Children’s Charity of Southern CA Poker and Casino Night on July 24, 2024.

12of 12

A Good Cause

Haley Joel Osment in 2024.Unique Nicole/Getty

Haley Joel Osment attends the 12th Annual Variety - The Children’s Charity Of Southern CA Poker And Casino Night at Paramount Pictures Studios on July 24, 2024 in Los Angeles, California.

Unique Nicole/Getty

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

source: people.com