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Jake Gyllenhaal has been in the spotlight for over 20 years, and since his debut in 1991's City Slickers, he's grown into major leading-man material. His breadth of work in films like Donnie Darko, Love & Other Drugs, Brokeback Mountain, and the new biopic Stronger prove Jake's ability to go from sweet to sexy to slightly scary in no time. We've rounded up the photos of him that show off his many (handsome) facets.

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Jake was suited up for the NYC premiere of Nightcrawler in October 2014.
Jake looked hot in his shades while attending the Dubai Film Festival in December 2015.
Jake and his sister, Maggie Gyllenhaal, were in stitches at the 2005 Vanity Fair Oscars party in LA.
He shed his shirt and took off running during a friendly softball game in August 2005.
Jake joined his Brokeback Mountain costars — Heath Ledger, Michelle Williams, and Anne Hathaway — for the film's premiere at the 2005 Toronto Film Festival.
He 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.
He wore a sleek, sexy tuxedo to the Oscars in 2011.
He cracked up on the red carpet with Life costar Ryan Reynolds at SXSW in March 2017.
Jake suited up for the Cannes Film Festival in May 2017.
Jake shared a cute onstage moment with Justin Timberlake as he presented Jake the best kiss award for his role in Brokeback Mountain at the 2006 MTV Movie Awards.
Susan Sarandon and Dustin Hoffman wanted to see more of Jake's six-pack at the Toronto Film Festival in September 2002 — we don't blame them!
He showed off facial scruff and slicked-back hair at the Toronto International Film Festival in September 2013.
Jake worked on his fitness in a behind-the-scenes video for the boxing movie Southpaw in July 2015.
He looked devilishly handsome at the Toronto Film Festival in September 2017.
Jake was all laughs while answering phones during Annual Charity Day in September 2017.
Jake sported a sleek suit and sexy scruff at the LA premiere of Prisoners in September 2013.
He gave a steely look in Paris in March 2017.
Jake and his then-girlfriend Kirsten Dunst made a cute couple at the London afterparty for The Day After Tomorrow in May 2004.
He shared a sweet moment with his mom, Naomi Foner, at the Sundance Film Festival in January 2013.
He bared his body while enjoying a Hawaiian getaway in June 2005.
Jake looked adorable at a Nightcrawler photocall in Toronto in September 2014.
Jake got scruffy at an event in NYC in November 2011.
Jake and Jennifer Aniston walked the red carpet together at the August 2002 premiere of their film, The Good Girl, in LA.
He hosted an LA screening of Blue Valentine for friends Ryan Gosling and Michelle Williams in December 2010.
George Clooney chatted with Jake between commercials at the 78th annual Academy Awards in March 2006.
Jake was all smiles on the sidelines with then-girlfriend Reese Witherspoon — the couple took in an LA Lakers game in January 2009.
Jake was one of the hot, up-and-coming actors in attendance at Teen Vogue's September 2003 Young Hollywood Party.
He couldn't stop laughing during a screening of Prisoners in Hollywood in November 2013.
Jake took his dog for a walk around LA's Runyon Canyon in September 2011.
He cut a handsome figure at the Everest premiere in Spetember 2015.
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