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Favorite Jake Gyllenhaal Movie Moments

Did you know Jake Gyllenhaal began his movie career playing Billy Crystal's son in "City Slickers"? Here's some great movie moments from the "Prince of Persia" star's career!

Favorite Jake Gyllenhaal Movie Moments

"City Slickers"(1991)

Character: Danny Robbins

Danny:“We saw a picture of you in a newspaper in your underwear.”
Kim (Walker Brandt): “Oh, well that was an advertisement. I sometimes model ladies' underwear.”
Barbara (Patricia Wettig): “You looked great.”
Danny: “Mom, you said let's see how she looks after having two kids.”

"October Sky" (1999)

Character:Homer Hickam

Homer:“Man, we should be trying to get into that science fair instead of sitting around here like a bunch of hillbillies.”
Roy Lee (William Lee Scott):"Well, I got some real sad news for you Homer. We “are” a bunch of hillbillies."

"Donnie Darko" (2001)

Character:Donnie Darko

Donnie:“I made a new friend today.”
Dr. Thruman (Katharine Ross):“Real or imaginary?”

"Bubble Boy" (2001)

Character:Jimmy Livingston

Slim (Danny Trejo):“What are you, some kind of Astronaut?”
Jimmy:“No, I’m some kind of bubble boy.”

"Lovely & Amazing" (2001)


Jordan:“Do you have a lot of friends?”
Michelle Marks (Catherine Keener):“No, actually I think people are too self-involved.”

"The Good Girl" (2002)

Character:Holden Worther

Justine (Jennifer Aniston):“Whatcha readin’?”
Holden:“Catcher in the Rye…I’m named after it.”
Justine:“What's your name?”
[Holden stares at her blankly]

"Moonlight Mile" (2002)

Character:Joe Nast

Bertie (Ellen Pompeo):“So, did you come back for that drink?”
Joe:[chuckles] “No, the dancing, actually.”

"The Day After Tomorrow" (2004)

Character:Sam Hall

Jeremy (Tom Rooney):“I thought you said it was too dangerous to go outside.”
Sam:“I know I did.”

"Brokeback Mountain" (2005)

Character:Jack Twist

Jack:“Brokeback got us good, don’t it?”

"Proof" (2005)


Catherine (Gwyneth Paltrow):“I didn’t find it.”
Hal:“Yes, you did.”
Catherine:“No, I didn’t.”
Hal:“I didn’t find it.”
Catherine:“I didn’t find it.I wrote it.”

"Jarhead" (2005)

Character:Anthony ‘Swoff’ Swofford

Swoff:“The marine must learn to kill.He may wear a tattoo, or display his medals, or tell lies in bars.But he is not a true marine until he has seen combat.”

"Zodiac" (2007)

Character:Robert Graysmith

Robert:“I just want to help.”
Ken (Donal Logue):“What are you a boy scout?”
Robert:“Eagle Scout, actually…First class.”

"Rendition" (2007)

Character:Douglas Freeman

Douglas:“This is my first torture.”

"Brothers" (2009)

Character:Tommy Cahill

Tommy:“I’d cut my throat to bring him back.”

"Prince of Persia" (2010)


Dastan:“Never trust a man who betrays his master, or take him into your service, lest he betray you as well.”