Academy Award nominee Jake Gyllenhaal is an A-list actor known as much for his high caliber acting, as for his classic good looks. While the name Gyllenhaal attached to a film usually means box office gold, the actor also isn’t afraid to tackle darker, quirky characters, or independent films.

If you, like so many others, are searching for a Gyllenhaal fix before the highly anticipated release of his film Prince of Persia: The Sands of Time, then check out this list of the best movies to see starring Mr. Gyllenhaal.

Zodiac (2007)

Set against the darkness that fell over San Francisco in the 1970’s with the emergence of the infamous and never identified Zodiac killer, Jake Gyllenhaal stars as cartoonist Robert Graysmith. The film – based on a book by the real-life Graysmith – chronicles the life and work of Gyllenhaal’s character as he risks is family life and career to try and identify the Zodiac killer.

During his investigation, Graysmith comes into contact with several suspects under very tense and creepy circumstances. The film leaves you wondering whether the Zodiac Killer slipped through the authorities’ fingers, and could still be out there somewhere.

Brokeback Mountain (2005)

For his role as Jack Twist in this sweeping tale of romance and loss, Jake Gyllenhaal earned an Academy Award nomination for Best Supporting Actor. Brokeback Mountain – directed by Oscar-winner Ang Lee – is based on the short story by Annie Proulx about two Wyoming cowboys and their secret love affair.

Beginning in 1963, the tale of these two ranchers – Gyllenhaal’s Jack Twist, and Ennis Del Mar played by the late Heath Ledger – and their incredibly gripping, passionate, and heartbreaking love story, spans nearly two decades. It encompasses their family life, and their battle with societal expectations, all set against an incredible landscape.

The Good Girl (2002)

Winner of the Independent Spirit Award for “Best Screenplay,” The Good Girl features Jake Gyllenhaal in one of his most powerful roles to date. Gyllenhaal stars as Holden Worther, who believes that he is a modern day version of Holden Caufield. Worther hates the world he lives in, and finds someone who shares these same sentiments in his co-worker Justine Last, played by Jennifer Aniston.

Last, who is married, struggles with her passionate feelings for Gyllenhaal’s character, and her safe, yet, mundane existence with her husband. Their affair leads to a dramatic series of events involving betrayal, blackmail, heartbreak, loss, and new life, all packaged in a dark comedy bundle.

Moonlight Mile (2002)

For this dramatic role, Gyllenhaal stars alongside acting heavyweights like Dustin Hoffman and Susan Sarandon. Gyllenhaal plays the lead role of Joe Nast – finance to Hoffman and Sarandon’s characters’ deceased daughter – who moves into his finance’s parents’ home to help them cope with the loss of their daughter. While living there, Nast struggles with the loss of his finance, and his budding feelings for a local girl.

Donnie Darko (2001)

Gyllenhaal’s mesmerizing portrayal of Donnie Darko made this “dark” film a cult classic. Donnie is a troubled young man who doesn’t have many friends or companions, save for a girlfriend named Gretchen, and an imaginary bunny named Frank. Frank shoes Donnie that the world is going to end, and through a series of mysterious circumstances and supernatural events, one begins to wonder if Donnie is insane, or if the fate of the world truly lies in his hands.

Watching any of these Gyllenhaal films is a great way to spend a movie night with your sweetie, or just indulge in a little Jake eye candy. For more Jake Gyllenhaal movie titles, please visit his IMDb profile.