According to Van Sant, a number of actors—including Leonardo DiCaprio and Brad Pitt—passed on the lead roles, which ultimately went to Heath Ledger and Jake Gyllenhaal. "Nobody wanted to do it," Van Sant, who nearly directed the Oscar-winning film, said. "I was working on it, and I felt like we needed a really strong cast, like a famous cast. That wasn't working out. I asked the usual suspects: Leonardo DiCaprio, Brad Pitt, Matt Damon, Ryan Phillippe. They all said no."
Looking back, Van Sant now thinks taking the unknown-actors approach might have helped him retain his excitement about the project. "I was not ready," he said. "I'm not sure why. There was just sort of a hiccup on my part. There was something off with myself, I guess, whatever was going on."
DiCaprio and Pitt will connect in Quentin Tarantino's upcoming star-stacked Once Upon a Time in Hollywood, which focuses on the 1969 Manson Family murders. "It's very hush-hush and top secret," Tarantino told CinemaCon attendees back in April. "But I can tell you that Once Upon a Time in Hollywood takes place in 1969, at the height of the counterculture hippie revolution and the height of new Hollywood." The surely great film opens July 26 of next year.