56 Mindboggingly Random Celebrity Couples From The Past 40 Years You Totally Forgot Ever Dated (2025)

We have a new celebrity couple that you would have never, ever guessed would be together in a millllllllion years. I'm of course talking about Billy Ray Cyrus and Elizabeth Hurley. Like... what?!?! Because I love a random forgotten celeb couple, here are 56 celeb couples who are almost as random as them... 1. Janet Jackson and Matthew McConaughey 2. Andre Agassi and Barbra Streisand 3. Scarlett Johansson and Jack Antonoff 4. John Mayer and Jessica Simpson 5. Kristen Johnston and Ryan Reynolds 6. Corey Feldman and Drew Barrymore 7. Topher Grace and Anne Hathaway 8. Deryck Whibley and Paris Hilton 9. Carmen Electra and Fred Durst 10. Marlee Matlin and John Stamos 11. Kim Basinger and Prince 12. Blake Lively and Kelly Blatz 13. Avril Lavigne and Brody Jenner 14. Avril Lavigne and Tyga 15. Diana Ross and Gene Simmons 16. Madonna and Vanilla Ice 17. Chris Evans and Christina Ricci 18. Jessica Biel and Chris Evans 19. Alanis Morissette and Ryan Reynolds 20. Cameron Diaz and Alex Rodriguez 21. Cody Simpson and Gigi Hadid 22. Miley Cyrus and Patrick Schwarzenegger 23. Megan Fox and David Gallagher 24. Pamela Anderson and Scott Baio 25. Serena Williams and Brett Ratner 26. Emma Stone and Kieran Culkin 27. Nicolas Cage and Lisa Marie Presley 28. Florence Pugh and Zach Braff 29. LeAnn Rimes and Andrew Keegan 30. Dennis Quaid and Shanna Moakler 31. Ricky Martin and Rebecca De Alba 32. Britney Spears and Colin Farrell 33. Nicole Kidman and Lenny Kravitz 34. Josh Hutcherson and Vanessa Hudgens 35. Michael Bublé and Emily Blunt 36. Jessica Simpson and Billy Corgan 37. Billy Corgan and Tila Tequila 38. Harry Styles and Olivia Wilde 39. Simon Cowell and Carmen Electra 40. Matthew Lawrence and Chilli 41. Brenda Song and Trace Cyrus 42. Gavin Newsom and Kimberly Guilfoyle 43. Katie Holmes and Jamie Foxx 44. Pete Davidson and Kate Beckinsale 45. Mandy Moore and Andy Roddick 46. Lance Armstrong and Sheryl Crow 47. Jennifer Lawrence and Chris Martin 48. Sarah Michelle Gellar and Jerry O'Connell 49. Freddie Prinze Jr. and Kimberly McCullough 50. Madonna and Tupac 51. Sandra Bullock and Jesse James 52. George Clooney and Stacy Keibler 53. Reese Witherspoon and Jake Gyllenhaal 54. Adrianne Curry and Christopher Knight 55. Mandy Moore and Zach Braff 56. And lastly, Ryan Gosling and Sandra Bullock