Jake Gyllenhaal has consistently worked in the biz since his first film at age 10. With so many movies to his credit, let's view his career standouts up to his latest, 'Demolition,' in which he portrays a man grieving the loss of his wife in a very unusual way.

Few might remember 'Demolition' star 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. View his career in pictures.

City Slickers (1991)

Then 9, Gyllenhaal took a small role as Billy Crystal's son in this hit comedy. After that, he had a couple of other bit parts, but his parents made him focus on school throughout his childhood, postponing showbiz until after graduation.

October Sky (1999)

This nostalgic drama about a coal miner's son with a love for rocketry put Jake Gyllenhaal on the map. After the film won over both critics and audiences, nobody could argue that the young actor was unable to hold a movie.

Donnie Darko (2001)

With this cult film about a disturbed high school student, Gyllenhaal revealed an eagerness to take on darker material. Even if 'Donnie Darko' failed to make a splash in theaters, its following grew quickly – as did its star's.

Moonlight Mile (2002)

Gyllenhaal made several interesting movies in the wake of 'Donnie Darko,' but this tearjerker about a man coping with his fiancée's death proved he could hold his own against such stars as Dustin Hoffman and Susan Sarandon.

The Day After Tomorrow (2004)

Even serious thespians find it hard to resist the lure of the big-budget blockbuster, and the environmentally conscious Gyllenhaal chose this eco-disaster film for his own.

Brokeback Mountain (2005)

Gyllenhaal received his first Oscar nomination (for Best Supporting Actor) alongside the late Heath Ledger in this instant classic about two closeted gay cowboys and their stormy relationship.

Jarhead (2005)

A bulked-up Gyllenhaal is at the center of this bleakly comic look at Gulf War Marines who have to contend more with boredom, desert heat and their own dwindling sanity than with the enemy.

Zodiac (2007)

David Fincher's chilly procedural about murder and obsession stars the actor as real-life newspaper cartoonist Robert Graysmith, who spends decades trying to identify San Francisco's mysterious Zodiac Killer.

Prince of Persia: The Sands of Time (2010)

An action flick based on a video game does seem a little beneath this actor's talent. Yet the star approaches the material with his trademark earnestness, even performing many of his own stunts.

Love & Other Drugs (2010)

Anne Hathaway played Gyllenhaal's lonely wife in 'Brokeback Mountain,' and the two stars reunite for this unconventional -- and very adult -- romantic comedy about a Viagra salesman and a woman stricken with early onset Parkinson's.

Source Code (2011)

This intelligent sci-fi thriller is the perfect vehicle for Gyllenhaal, who portrays a soldier assigned to stop a bomb on a Chicago-bound train – over and over again, in a twisty plot that presages 'Edge of Tomorrow.'

End of Watch (2012)

Gyllenhaal's recent run of strong parts in smaller, high quality films is exemplified by this realistic drama. He plays an L.A. cop who, with his partner (Michael Peña), is just trying to do his job while being targeted by vindictive gangsters.

Enemy (2013)

Gyllenhaal made two back-to-back thrillers with Canadian director Denis Villeneuve. The first, 'Prisoners,' was a solid hit. The more challenging 'Enemy' is the second film, with the actor playing doppelgängers. Some say this, and his performance in 'Nightcrawler,' represent his best work.

Nightcrawler (2014)

Many thought Gyllenhaal was robbed by not getting an Oscar nomination (he did get a Golden Globe nod) for his role as a bottom-feeding pseudo journalist who chases graphic news stories, and in doing so becomes one of them himself.

Southpaw (2015)

Not just another genre movie, this boxing drama sees Gyllenhaal fully inhabit former champ Billy, who must fight back from the depths and earn back his daughter's respect.