37. Brokeback Mountain (2005)
Director: Ang Lee
Stars: Heath Ledger, Jake Gyllenhaal, Michelle Williams, Anne Hathaway, Randy Quaid, Linda Cardellini, Anna Faris, David Harbour, Kate Mara
If you're the type who can't watch a single moment of Ang Lee's superb and heartbreaking love story Brokeback Mountain without uttering the words “pause” or “a-yo,” then we suggest you click on over to Grandma's Boy (which, yes, is also on this list—how's that for open-mindedness?). For those able to exude maturity and appreciate stellar storytelling and tremendous, Brokeback Mountain, led by Jake Gyllenhaal's and the late Heath Ledger's magnificent performances as gay cowboys, is one of the Complex decade's strongest romances, and, most importantly, emotionally affecting movies.