Few might remember Jake Gyllenhaal’s early start as a child actor, but he’s actually been in the biz since age 10—practically two decades. Over the last 20 years, he’s gone from boy to—ahem—quite a man, as these pics show. We look back on the recently-beefed-up Prince of Persia star’s career (did we say look? Now! Do It!) in this photo retrospective.
City Slickers (1991)
Jake was 10 when he made his acting debut as Billy Crystal’s son in this comedy about three city-dwelling buddies who head off to a two-week cattle drive to get away from it all. In one scene, he embarrassedly introduces his ad-exec dad speaker to a disappointed and bored class, in another he pulls faces and shows off in front of guests at a party.
Homicide: Life on the Street (1994)
Jake appeared in the second season’s first episode, which to this date remains the NBC series’ most-watched episode most likely because Robin Williams was in it as a man whose wife is killed in front of the family. Jake played his angry son.
An early promo shot.
October Sky (1999)
After graduating from Los Angeles’ Harvard-Westlake School in 1998, Jake appeared in his first leading role as a young West Virginia man hoping to avoid his destiny as a coal miner by attempting to win a science scholarship. It was known as his first breakout role, one that landed his next major film…
Donnie Darko (2001)
This cult favorite starred Jake as a troubled kid who has visions of a giant rabbit named Frank who warns him of the world’s end. Though not a success when it was released, it became known as a benchmark in Jake’s career and he established himself as a bona fide member of Young Hollywood.
Jake in 2001
Jake, at about 20-21 years old.
Lovely & Amazing (2001)
Still often cast as a teenager, here Jake plays Jordan, who becomes the object of affection for his much-older photomat coworker with a troubled marriage.
The Good Girl (2002)
Though it might be best known for showcasing Jennifer Aniston's first respected screen role, Jake played a big part as the deep-thinking, depressive Holden, who basically hates his mundane life and meets a tragic end.
Bubble Boy (2001)
This rom-com based on the life of a sick boy who has to live life sealed in a sterile environment was generally panned by critics, and is probably one Jake would like to leave behind in the annals of forgotten films.
Jake in 2002
Slowly the teen years are falling away...
An early 2000's promo pic
Another critically disappointing effort was this film, in which Jake starred opposite Jared Leto as a screwed-up drug dealer. What's with the spider tattoo?
Moonlight Mile (2002)
Though critics were divided on the film's story, about a man dealing with his fiancee's death and her grieving family, most recognized Jake's performance as outstanding.
The Day After Tomorrow (2004)
He may have lost Spider-man to Tobey Maguire, but no big deal--he made this one directed by Roland Emmerich his first blockbuster action film. Critics were lukewarm, but audiences loved it.
OK, we just threw this one in there. Bonus!
Brokeback Mountain (2005)
Jake and the late Heath Ledger played young sheepherders in the '60s who embark on a forbidden relationship in this, commonly referred to as "the gay cowboy movie" even though the characters' true sexuality wasn't defined. The role got him a Supporting Actor Oscar nomination.
This time, Jake played not a sensitive, brooding type, but a manly, violent Marine in the first Gulf War.
We just liked this shot. Maybe it's the blue eyes...
He starred in David Fincher's tale based on the real life Zodiac killer as an intrepid reporter hot on the case. The killer was never found--but did destroy Jake's character's marriage.
In this remake of a Danish film, he plays the brother of a disturbed vet who returns from Afghanistan to suspicions that his wife has been cheating--with Jake's character.
Jake in 2010
Now 29, Jake has established himself as one of Hollywood's foremost young stars. After Persia, look out for him to star in the rom-com Nailed with Jessica Alba, the Viagra comedy Love and Other Drugs, and the sci-fi actioner Source Code, all in the next year or so.