1/27Sarah Jessica Parker and Robert Downey Jr. at the Oscars in 1989. The duo dated for around seven years but broke it off due to Downy Jr’s drug addiction. Picture: Getty
Oscars’ oddest couples
DATE night at the Oscars has never been so awkward, check out all the surprising Oscars pairings you’ve forgot were ever a thing.
2/27Madonna and Michael Jackson at the Oscars in 1991. Picture: Getty
3/27Cher, son Elijah Blue Allman and Val Kilmer at the Oscars in 1980. Picture: Getty
4/27Cindy Crawford and Richard Gere at the Oscars in 1991. Picture: Getty
5/27Tom Green and Drew Barrymore at the Oscars in 2000. Picture: Getty
6/27Ferris Matthew Broderick and Jennifer Grey at the Oscars in 1987. The pair starred as siblings in classic 1986 film Ferris Bueller’s Day Off. Picture: Getty
7/27Naomi Watts and Heath Ledger at the Oscars in 2004. Picture: Getty
8/27Ellen DeGeneres and Anne Heche at the Oscars in 1999. Picture: AAP
9/27Jack Nicholson and Anjelica Huston at the Oscars in 1975. Picture: Getty
10/27Brad Pitt and Gwyneth Paltrow at the Oscars in 1996. Picture: AAP
11/27Angelina Jolie and brother James Haven at the Oscars in 2000. Picture: Getty/Corbis
12/27Brad Pitt and Juliette Lewis at the Oscars in 1992. Picture: AAP
13/27Jennifer Aniston and John Mayer at the Vanity Fair Oscar party in 2009. Picture: AAP
14/27Jude Law and Sienna Miller at the Oscars in 2004. Picture: Getty
15/27Michael Jackson and Brooke Shields at the Oscars in 1981. Picture: Getty
16/27Julia Roberts and Kiefer Sutherland at the Oscars in 1991. Picture: Getty
17/27Matt Dillon And Cameron Diaz at the Oscars in 1998. Picture: Getty
18/27Leonardo DiCaprio and Gisele Bündchen at the Oscars in 2005. Picture: Getty
19/27Jennifer Lopez and actor Ben Affleck at the Oscars in 2003. Picture: Getty
20/27Drew Barrymore, Edward Norton and Liv Tyler at the Oscars in 1999. Picture: Getty
21/27Kirsten Dunst and Jake Gyllenhaal at the Vanity Fair Oscar Party in 2004. Picture: AAP
22/27Winona Ryder and Christian Slater at the Oscars in 1989. Picture: Getty
23/27Paul McCartney and Heather Mills at the Oscars in 2002. Picture: AAP
24/27MUST CREDIT GETTY WEB RIGHTS ONLY Drew Barrymore & Liv Tyler (Photo by SGranitz/WireImage)
25/27HOLLYWOOD, CA - FEBRUARY 29: Actress Naomi Watts, nominated for Best Actress for her performance in "21 Grams" (L) and Actor Heath Ledger attend the 76th Annual Academy Awards at the Kodak Theater on February 29, 2004 in Hollywood, California. (Photo by Carlo Allegri/Getty Images)
26/27Michael Jackson and Brooke Shields (Photo by Ron Galella/WireImage)
27/27Michael Jackson and Brooke Shields (Photo by Ron Galella/WireImage)
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