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 nearly 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.
16. In another universe, Evan Rachel Wood could’ve ended up in Lindsay Lohan’s role, Cady, in Mean Girls (she declined); Lindsay Lohan could have ended up playing Rachel McAdams’ Regina George (as initially planned), and Scarlett Johansson — who tested — could’ve ended up as Karen Smith, the role played by Amanda Seyfried.
17. Mae Whitman was John Green’s first choice to play the female lead (Shailene Woodley’s role) in Fault in our Stars, while Nat Wolff auditioned for the male lead, which went to Ansel Elgort.
18. Molly Ringwald was offered the role of Sidney (Neve Campbell) in Scream, but declined because she didn’t want to play high-schoolers anymore at the age of 27; Joaquin Phoenix turned down Skeet Ulrich’s role, Billy Loomis; and before Courtney Cox landed the role of Gale Weathers, Janeane Garofalo and Brooke Shields turned it down, and the offer to Elizabeth Berkley was pulled due to the Showgirls backlash.
19. Blake Lively turned down the role that eventually went to Megan Fox in Jennifer’s Body.
20. Henry Cavill was the first choice to play Edward (Robert Pattinson) in Twilight, but he was too old for the role by the time production began; Jennifer Lawrence was considered for the role of Bella (Kristen Stewart).
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