The aughts were a different time, so much so that apparently many actors passed on the 2005 film and what ended up being two of the most iconic roles of all times. Brokeback Mountain, starring Jake Gyllenhaal and the late Heath Ledger , explores a 20-year affair between two characters Jack Twist and Ennis Del Mar (a groundbreaking story for its time considering it was ten years before same-sex marriage was made legal in the United States). In an interview with Indiewire , Don’t Worry, He Won’t Get Far on Foot director Gus Van Sant opened up about the difficulties of Brokeback Mountain, which he was originally slated to direct before it eventually went to Ang Lee.