Seal and Tyra Banks
Now known for his marriage to supermodel Heidi Klum, we always forget that Seal actually made a habit of dating Victoria’s Secret Angels. He dated Tyra Banks in 1996.
Angelina Jolie and Billy Bob
The pair met while filming Pushing Tin in 1999 and married shortly after. When they divorced in 2002, Jolie took custody of adopted son Maddox.
Sarah Jessica Parker and Robert Downey Jr.
Wild child Robert Downey Jr. and Hollywood Sweetheart Sarah Jessica Parker were an item in the 1980s. The pair eventually separated because of Downey’s partying ways.
photo: robertdowneyjuniorfoto.blogspot.com
Cindy Crawford and Richard Gere
Richard Gere was married to the supermodel from 1991 to 1995.
Ryan Gosling and Sandra Bullock
This odd couple of Hollywood’s dream man and leading comedic lady happened quietly in 2003 and stayed fairly out of the headlines.
Ryan Reynolds and Alanis Morissette
Remember when these two were engaged in 2007? Yes, it really happened. The Canadian couple dated in the early 2000s before breaking off their engagement.
photo: thesmogger.wordpress.com
Brad Pitt and Christina Applegate
Brad Pitt is no stranger to celebrity couples. Before there was Angelina Jolie and Jennifer Aniston, there was Christina Applegate. The pair went to the 1989 MTV Movie Awards together before breaking it off.
Owen Wilson and Sheryl Crow
The pair dated in the early 2000s and Crow released “Safe and Sound” about Wilson
Tara Reid and Carson Daly
This couple was the “it” couple in the late 90s but broke off their engagement in 2001.
Whitney Houston and Ray J
Perhaps the most unexpected pair on the list, Houston dated a much younger Ray J in 2008.
