Look Back at Jake Gyllenhaal’s Fresh-Faced Moments in Hollywood

Since his childhood acting days, Jake Gyllenhaal has captured Hollywood's attention. Look back at the star's young years on his birthday.

Photo: Getty Images.

Jake Gyllenhaal has always been a big name in Hollywood. As a child actor, he was destined to be a star along with his older sister Maggie Gyllenhaal from a young age. A ‘90s heartthrob by the end of the decade, the Oscar-nominated actor has a legacy of notable roles in Donnie Darko, Brokeback Mountain, and more, along with on and off-screen romances with fellow co-stars.

Impressive at any age, L’OFFICIEL looks back at the actor’s most memorable young roles and romances in honor of his 42nd birthday today.

1 / 12

Gyllenhaal stars as Billy Crystal’s son in the movie “City Slickers.” It was his debut film role at age 10, but he didn’t begin acting full-time until his teen years.

In the ‘90s, his father, director Stephen Gyllenhaal, cast the young actor in his films “A Dangerous Woman” and “Homegrown.”

A 13-year-old Gyllenhaal appears in the fantasy-adventure film “Josh and S.A.M.” as Leon, a friend of the film’s main character. The child actor’s floppy hair and polka-dotted button down scream of a ‘90s childhood look.

A teen Gyllenhaal sports spiky hair in the '90s.

Close with his sister Maggie, the two Gyllenhaal siblings collaborated often in their youth, co-starring in films like 2001’s “Donnie Darko.”

Growing into a cult classic, Disney’s “Bubble Boy” features Gyllenhaal as a spiky-haired immuno-compromised boy. The film was meant to make Gyllenhaal, then age 21, a star, but was largely considered a controversial comedy at the time of its release.

“October Sky” is based on the real childhood experiences of Homer Hickam, a NASA engineer from Coalwood, West Virginia. The actor plays the young engineer alongside Laura Dern and Chris Cooper.

Gyllenhaal plays the titular character Donnie Darko in 2001’s cult classic movie of the same name. The film premiered at Sundance Film Festival, and follows Gyllenhaal’s Donnie as he experiences visions of monstrous Frank who tells him the world is ending.

In “The Good Girl,” Gyllenhaal stars opposite a young Jennifer Aniston. The hyper-realistic film shows the heart wrenching romantic journey of the two characters who meet while working at a Texas discount store.

A youthful Gyllenhaal and Ellen Pompeo (“Grey’s Anatomy”) feature in the 2002 drama “Moonlight Mile” alongside Dustin Hoffman and Susan Sarandon.

Who can forget the famous image of It couple Kirsten Dunst and Gyllenhaal eating together in Paris? The two stars dated in the early 2000s after being set up by Gyllenhaal’s sister.

Gyllenhaal remains good friends with actress Natalie Portman, who he also dated in the early 2000s.