1991

Jake Gyllenhaal

June 07

City Boy

At 11, Gyllenhaal gets his first taste of the big screen with a small role as Billy Crystal's son, Danny, in the summer hit City Slickers. The movie grabs more than $124 million at the domestic box office.

1999

February 19

Rocket Man

In October Sky, the actor plays NASA engineer Homer Hickman Jr., one of several young men trying to become rocket scientists to avoid mining. Entertainment Weekly credits Gyllenhaal for saving "the film from two-dimensionality" with his "passionate performance."

2001

Jake Gyllenhaal

August 24

First Flop

Gyllenhaal stars in the comedy Bubble Boy about a teen with a deficient immune system. Although the film is a commercial flop, earning just over $5 million, Gyllenhaal never regrets starring in the film. "Know what's interesting about that movie? The result just wasn't the process. The process of that movie was wonderful!" he tells GQ in 2007. "A lot of people talk about other movies I've done as being very courageous – but I want to go to more places with that intention. To me, that's a success."

Jake Gyllenhaal

October 26

Becoming a Cult Hero

Gyllenhaal stars in Donnie Darko. His portrayal of a sullen, schizophrenic teenager who hears voices in his head from a man-size rabbit with a twisted-mask, makes him a cult superhero. Although the film flops at the box-office, it becomes "the trippy underground hit of a generation," according to Entertainment Weekly. "Every day someone comes up and is like, 'Donnie Darko man...f---! We gotta talk about it,'" he tells EW.

2002

March

Big Thespian

Gyllenhaal tries his hand at theatre in the London production of This is Our Youth with Hayden Christensen and Anna Paquin. The performance leads to a role in director Sam Mendes' Jarhead. "I don't think I had realized until I saw him onstage how masculine he was," Mendes tells Premiere magazine. "He's a big guy and he has a combination of soulfulness and 'man of action' I was looking for."

Jake Gyllenhaal

September

Love Connection

After Gyllenhaal lends his support to sister Maggie at the September 18 premiere of her movie Secretary, she helps her brother in return, introducing him to her pal Kirsten Dunst, who becomes his girlfriend.

September 27

Hunk on the Set

While shooting the romantic drama Moonlight Mile, Gyllenhaal sets hearts ablaze behind the scenes: "Everyone had crushes on him – wardrobe, makeup, everybody," his costar Aleksia Landeau tells PEOPLE. "He's not like those actors who are like, 'Look at me!' He has a poetic soul. He lets people come to him."

Jake Gyllenhaal

December 02

Making the Cut

Gyllenhaal wins a spot in PEOPLE's Sexiest Man Alive issue. "He's gorgeous, and he's got those big dreamy eyes," his Moonlight Mile costar Susan Sarandon tells the magazine. "A lot of eyes can't offer 'I love you' in a convincing way. With Jake, you believe he has the capability and the depth to love. That's awesomely attractive." Gyllenhaal will make another appearance in the issue in 2006.

2004

Jake Gyllenhaal

March

Puppy Love

Gyllenhaal and girlfriend Dunst adopt a 6-month-old German shepherd mix they name Atticus after the main character in Gyllenhaal's favorite book To Kill A Mockingbird.

Jake Gyllenhaal

May 28

Action!

Gyllenhaal stars in The Day After Tomorrow. The action blockbuster adventure is a transition for the indie film star, who doesn't apologize for taking the role. "Choices are choices. I had done five movies in a row that asked a lot of me, and just wanted to run around," Gyllenhaal tells Entertainment Weekly. "It wasn't necessarily realistic, but I liked that it said something relevant."

Photo Credits

BIOGRAPHY (top to bottom): CASTLE ROCK; touchstone; Kobal Collection/Wireimage; Eric Charbonneau/BEImages; Armando Gallo/Retna; STEVE KONDILIS/BAUER-GRIFFIN; 20th Century FOX/Everett

Edited by Julia Wang

Jake Gyllenhaal

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