POPSUGAR Celebrity

33 Sweet, Sexy Jake Gyllenhaal Moments

Dec 19 2013 - 4:05pm

Today is Jake Gyllenhaal [1]'s 33rd birthday! He's been in the spotlight for almost 20 years, and since his debut in 1991's City Slickers, Jake has grown into major leading-man material. Take a look back at some of his sexiest and sweetest pictures through the years — happy birthday, Jake!

Jake Gyllenhaal [2] wore a sleek, sexy tuxedo to the Oscars in 2011.

Kirsten Dunst [3] and Jake stuck close at the 2004 Vanity Fair Oscar party in LA.

Jake did his best "hey, girl" while arriving for an appearance on the Late Show in NYC in May 2010.

Jennifer Aniston [4] shared a congratulatory kiss with Jake at the 2007 GLAAD Media Awards in LA.

Jake put his buff body on display during a July 2011 vacation in Hawaii.

Jake stopped to sign autographs for fans in the bleachers at the Screen Actors Guild Awards in January 2006.

Jake shared a sweet moment with his mom, Naomi Foner, at the Sundance Film Festival in January 2013.

Jake and his then-girlfriend Kirsten Dunst [5] made a cute couple at the London afterparty for The Day After Tomorrow in May 2004.

George Clooney [6] chatted with Jake between commercials at the 78th Annual Academy Awards in March 2006.

He perfected his horse-riding during a Summer trip to London in 2008.

Jake was one of the hot, up-and-coming actors in attendance at Teen Vogue's September 2003 Young Hollywood Party.

He bared his body while enjoying a Hawaiian getaway in June 2005.

Jake shared a cute onstage moment with Justin Timberlake [7] as he presented Jake the best kiss award for his role in Brokeback Mountain at the 2006 MTV Movie Awards.

Jake and his sister Maggie Gyllenhaal [8] were in stitches at the 2005 Vanity Fair Oscars party in LA.

Jake stepped out to support his sister, Maggie, at the Toronto Film Festival screening of her movie Secretary in 2002.

He couldn't stop laughing during a screening of Prisoners in Hollywood in November 2013.

He and Zooey Deschanel [9] performed a silly skit together during the 2004 Sundance Film Festival Awards.

Jake joined his Brokeback Mountain costars — Heath Ledger [10], Michelle Williams [11], and Anne Hathaway [12] — for the film's premiere at the 2005 Toronto Film Festival.

He got cute with family and friends during his dad's Hawaiian wedding [13] in July 2011.

He and his Love and Other Drugs costar Anne Hathaway [14] posed together in Sydney, Australia in December 2010.

Susan Sarandon and Dustin Hoffman [15] wanted to see more of Jake's six-pack at the Toronto Film Festival in September 2002 — we don't blame them!

Jake and Jennifer Aniston [16] walked the red carpet together at the August 2002 premiere of their film, The Good Girl, in LA.

Jake hosted an LA screening of Blue Valentine for friends Ryan Gosling [17] and Michelle Williams [18] in December 2010.

Jake sported a sleek suit and sexy scruff at the LA premiere of Prisoners in September 2013.

Jake and his Brothers costar Tobey Maguire [19] cracked up during the LA Variety screening of the film in December 2009.

He was all smiles at the New Orleans Jazz Festival in April 2011.

Jake celebrated Bastille Day in Paris with then-girlfriend Reese Witherspoon [20] and her daughter, Ava Phillippe, in July 2008.

Jake took his dog for a walk around LA's Runyon Canyon in September 2011.

Jake shed his shirt and took off running during a friendly softball game in August 2005.

Jake got scruffy at an event in NYC in November 2011.

He spent time with his niece, Ramona Sarsgaard, around NYC in November 2011.

Jake couldn't help but laugh while presenting onstage with Heath Ledger [21] at the SAG Awards in January 2006.

Jake was all smiles on the sidelines with then-girlfriend Reese Witherspoon [22] — the couple took in an LA Lakers game in January 2009.

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