28 Famous Couples I, For One, Cannot Believe Were Actually Together
Bradley Cooper and Renée Zellweger were so stinkin' cute!
1. Madonna and Warren Beatty

When they were together: For 15 months from 1990–1991.
2. Kate Hudson and Alex Rodriguez

When they were together: 2009.
3. Jennifer Lopez and Wesley Snipes

When they were together: 1995.
4. Brad Pitt and Robin Givens

When they were together: The late '80s.
5. Sarah Paulson and Cherry Jones

When they were together: 2005–2009.
6. Taraji P. Henson and Common

When they were together: 2005.
7. Renée Zellweger and Bradley Cooper

When they were together: 2009–2011.
8. Zooey Deschanel and Jason Schwartzman

When they were together: 2003–2005.
9. Jaden Smith and Sofia Richie

When they were together: 2012.
10. Zoë Kravitz and Penn Badgley

When they were together: 2011–2013.
11. Kristen Stewart and St. Vincent

When they were together: 2016.
12. Gwyneth Paltrow and Ben Affleck

When they were together: On-and-off from 1997–2000.
13. Rashida Jones and Mark Ronson

When they were together: They were engaged in 2003.
14. Ciara and 50 Cent

When they were together: 2007–2010.
15. Jennifer Aniston and Adam Duritz

When they were together: 1995.
16. Angelina Jolie and Jenny Shimizu

When they were together: 1996.
17. Fred Armisen and Elisabeth Moss

When they were together: 2009–2010.
18. Lenny Kravitz and Nicole Kidman

When they were together: They were briefly together (and eventually engaged) from 2002–2003.
19. Carrie Fisher and Dan Aykroyd

When they were together: They were briefly engaged while filming The Blues Brothers in 1979.
20. Diana Ross and Gene Simmons

When they were together: 1979–1984.
21. Madonna and Jean-Michel Basquiat
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When they were together: In the early '80s before Madonna made it big.
22. Linda Perry and Clementine Ford

When they were together: 2009–2010.
23. Drew Barrymore and David Arquette

When they were together: 1991.
24. Busy Philipps and Colin Hanks

When they were together: In the late '90s when they attended Loyola Marymount University.
25. Barbra Streisand and Elliott Gould

When they were together: They were married from 1963–1971.
26. Mariah Carey and Derek Jeter

When they were together: 1997–1998.
27. Carly Simon and James Taylor

When they were together: They were married from 1972–1983.
28. And Ted Danson and Whoopi Goldberg

When they were together: 1992–1993.