The 30 most outrageous celebrity feuds appeared in the show are these: 30. Heidi Kum vs. Elle McPherson. 29. Lindsay Lohan vs. Hilary Duff. 28. Paul McCartney vs. Heather Mills. 27. Christina Aguilera vs. Mariah Carey. 26. Madonna vs. Elton John. 25. Denise Richards vs. Charlie Sheen. 24. David Letterman vs. Oprah Winfrey. 23. Tom Cruise vs. Sumner Redstone. 22. Kimberly Stewart vs. Cisco Adler. 21. Stephen Dorff vs. Jeremy Piven. 20. Shanna Travis Barker vs. Paris Hilton. 19. Bill O'Reilly vs. George Clooney. 18. Kelly Osbourne vs. Christina Aguilera. 17. Shannen Doherty vs. Jennie Garth. 16. Kim Cattrall vs. Sex and the City (1998). 15. Josh Duhamel vs. Tommy Lee. 14. Toby Keith vs. The Dixie Chicks. 13. Matt Stone & Trey Parker vs. Comedy Central. 12. Patrick Dempsey vs. Isaiah Washington. 11. Naomi Campbell vs. Tyra Banks. 10. Britney Spears vs. Justin Timberlake. 9. Eminem vs. the world. 8. Anna Nicole Smith vs. Pierce Marhsall. 7. Heather Locklear vs. Denise Richards. 6. Donald Trump vs. Martha Stewart. 5. Tom Cruise vs. Brooke Shields. 4. Rosie O'Donnell vs. Star Jones Reynolds. 3. Lindsay Lohan vs. Brandon Davis. 2. Tori Spelling vs. Candy Spelling. 1. Paris Hilton vs. Nicole Ritchie.