1. Juliette Lewis — yes, that Juliette Lewis — was originally offered the lead of Mia Thermopolis in Princess Diaries, which would eventually go to the more age-appropriate Anne Hathaway, who was nine years younger.
2. Josh Hartnett and Ashton Kutcher got beat out by Heath Ledger for the role of Patrick in 10 Things I Hate About You.
3. Based on the audition process, the cast of Clueless could’ve ended up with this composition: Reese Witherspoon as Cher, Terrence Howard as Murray, Zooey Deschanel as Tosh, Seth Green as Travis and Lauryn Hill for Dionne.
4. Kirk Cameron was nearly cast as Lloyd Dobler instead of John Cusack in Say Anything. KIRK CAMERON.
5. Elijah Wood was originally cast opposite Melissa Joan Hart in Drive Me Crazy, but he was replaced by Adrian Grenier because Wood looked too young.
6. Melissa Joan Hart was originally offered the role of Julie James (Jennifer Love Hewitt) in I Know What You Did Last Summer.
7. The part of Veronica (Winona Ryder) in Heathers was written for Jennifer Connelly, but she turned it down. Likewise, Brad Pitt was rejected for the part of J.D. (Christian Slater) because he was “too nice.”
8. Gary Oldman was first offered the title role in Edward Scissorhands, while Tom Cruise, Jim Carrey and Robert Downey Jr. were all considered before Tim Burton landed on Johnny Depp, who drafted Winona Ryder away from The Godfather III, so you can blame Depp for Sofia Coppola’s appearance in Godfather III.
9. Ironically, Joshua Jackson (R.I.P.) was also considered for the role of Mox in Varsity Blues, which Jackson’s “Dawson’s Creek” co-star, James Van Der Beek, would land.
10. Logan Lerman auditioned for the role in Easy A that would go to Dan Byrd. Fortunately, Emma Stone (whose audition reel was the actual webcam footage at the beginning of the film) left Zack Snyder’s Sucker Punch to do Easy A.
11. Jim Carrey and Ally Sheedy nearled ended up in Anthony Michael Hall and Molly Ringwald’s roles in 16 Candles.
12. Clint Howard was considered for the role of Ricky in Better Off Dead, the movie that John Cusack now famously hates because John Cusack is a douche.
13. Stephen Dorff was considered for Wil Wheaton’s role in Stand by Me.
14. Rob Lowe, John Cusack, Jim Carrey, Johnny Depp, Tom Cruise, Robert Downey Jr. and Michael J. Fox were all considered for the role of Ferris Bueller while both Anthony Michael Hall and Emilio Estevez turned down the role of Cameron.
15. Paul Newman was considered for James Dean’s role in Rebel without a Cause.