The 96th Annual Academy Awards are right around the corner, and we’re looking back on the red carpet tradition we’ve always loved most: the chance for couples to take their highly photographed stroll down the red carpet. There’s so much we can read into who our favorite celebrities have chosen to take to the Oscars over the years, as it’s usually not an honor bestowed lightly and is often saved for fiancés, spouses, or in some cases relatives.
To give you a modern-day example: It’s a no-brainer that we have pics of Ben Affleck with his wife Jennifer Lopez and ex-wife Jennifer Garner on the red carpet over the years. But if Affleck had attended this year’s Oscars with ex-girlfriend Ana de Armas? That would have been a major, major moment in that couple’s history — and a sign that things were getting really serious.
While it’s easy to think of recent splits that broke our hearts, like still-fresh Jodie Turner-Smith and Joshua Jackson, there are so many all-time favorite former couples who have stunned at the Oscars over the years. It’s not just go-to “it” couples like Brad Pitt and Angelina Jolie hiding out in photos from the 1980s through the 2000s, but couples we honestly forgot ever dated: Salma Hayek and Ed Norton, anyone?
Whether you’re a fan of these stars’ current partners or wish celebs would just go back to their ’90s pairings, there’s no denying these actors have evolved in more ways than one in their Academy Awards photos over the years. See our favorite exes to attend the Oscars together as a couple below.
A version of this article was originally published in 2021.
Robert Downey Jr. & Sarah Jessica Parker
Sarah Jessica Parker and Robert Downey Jr. looked so cute as they cuddled up at the 61st Annual Academy Awards in 1988. The pair dated for seven years from 1984 to 1991.
Cindy Crawford & Richard Gere
Richard Gere and Cindy Crawford wowed in black and white looks at the 65th Annual Academy Awards in 1993. The pair, who tied the knot in 1991, broke things off four years later in 1995.
Madonna & Michael Jackson
Michael Jackson and Madonna looked giddy as they attended Swifty Lazar’s Academy Awards after-party in 1991. The pair only dated for a brief period in the 90s.
Julia Roberts & Kiefer Sutherland
Exes Julia Roberts and Kiefer Sutherland looked so happy together at the 63rd Annual Academy Awards in 1991. The pair, who began dating in 1988, was set to walk down the aisle in 1991. That is, however, until Roberts called it quits before the ceremony even took place.
Brad Pitt & Juliette Lewis
Brad Pitt took a special plus one with him to the 64th Annual Academy Awards in 1992: his girlfriend Juliette Lewis. The pair dated from 1989 to 1993.
Hugh Grant & Elizabeth Hurley
Hugh Grant and Elizabeth Hurley looked like a true Hollywood power couple at the 67th Annual Oscars in 1995. The duo dated for 13 years before splitting up in 2000.
Brad Pitt & Gwyneth Paltrow
Brad Pitt and Gweneth Paltrow were all smiles at the 68th Annual Academy Awards in 1996.
The stylish former couple dated from 1994 to 1997.
Patricia Arquette & Nicholas Cage
Patricia Arquette and Nicholas Cage arrived in style at the 69th Annual Academy Awards back in 1997. The two married in April 1995 and their divorce was finalized in 2001.
Jack Nicholson & Rebecca Broussard
At the 1993 Oscars, Jack Nicholson was joined by his girlfriend Rebecca Broussard at the 65th Annual Academy Awards. The pair were together from 1989 to 1994 and share kids Lorraine and son Ray Nicholson.
Matt Dillon & Cameron Diaz
Matt Dillon and Cameron Diaz looked like 1990s perfection at the 70th Annual Academy Awards in 1998. The pair broke things off a few months later after three years of dating.
Billy Bob Thornton & Laura Dern
Former lovebirds Billy Bob Thornton and Laura Dern looked so chic at the 1999 Oscars. The pair, who had been together since 1997, broke things off when Thornton left Dern to pursue a relationship with Angelina Jolie in 1999.
Ellen DeGeneres & Anne Heche
The late Anne Heche and Ellen DeGeneres looked so happy as they proudly walked the carpet for the 71st Annual Academy Awards in 1999. As one of Hollywood’s first openly gay couples, the two made history, despite only dating for three years from 1997 to 2000.
Tom Cruise & Nicole Kidman
Tom Cruise has never looked happier than when he attended the 72nd Annual Academy Awards with his then-wife Nicole Kidman. The pair, who share kids Isabella and Connor, were married from 1990 to 2001.
Marc Anthony & Jennifer Lopez
Marc Anthony and Jennifer Lopez were all smiles at the 78th Academy Awards in 2006.
The former couple, who share twins children Emme and Max, were married from 2004 to 2011.
Heather Graham & Edward Burns
Heather Graham and Ed Burns looked like on powerful couple at the 2000 Oscars. The pair split later than year after two years of dating.
Jennifer Aniston & Brad Pitt
All eyes were on Jennifer Aniston and Brad Pitt when they attended the 2000 Oscars. The pair were married from 2000 to their shocking split in 2005.
Julia Roberts & Benjamin Bratt
Benjamin Bratt was right by his girlfriend Julia Roberts’ side when she won the Best Actress in a Leading Role award at the 2001 Oscars. The pair dated from 1997 to 2001.
Kate Hudson & Chris Robinson
Kate Hudson and her husband at the time Chris Robinson attended the 75th Annual Academy Awards right beside each other in 2003. The pair were married from 2000 to 2007 and share 20-year-old son Ryder Robinson.
Salma Hayek & Edward Norton
As one of the couples we most forget even existed, Salma Hayek and Edward Norton walked the red carpet together at the 75th Annual Academy Awards in 2003. The pair dated for four years until their split in 2003.
Jennifer Lopez & Ben Affleck
They may no longer be exes, but we couldn’t resist including them on this list: Jennifer Lopez and Ben Affleck looked like Hollywood royalty at the 75th annual Academy Awards in 2003.
As we know, the two broke off their first engagement in 2004. Years later, in 2021, the pair reunited and happy been happily in love ever since.
Jude Law & Sienna Miller
Jude Law looked so in love with Sienna Miller at the 76th annual Academy Awards Vanity Fair Oscar Party in 2004.
The pair eventually broke up in 2005 after Miller found out about Law’s affair with their nanny.
Leonardo DiCaprio & Gisele Bündchen
Leonardo DiCaprio and Gisele Bündchen proved they were one of the most beautiful couples Hollywood has ever seen as they walked the carpet at the 2005 Oscars together.
The pair dated on and off for five years until they split in 2005.
Reese Witherspoon & Ryan Phillippe
Reese Witherspoon and Ryan Phillippe looked like an IRL fairytale at the 78th Annual Academy Awards in 2006. The former couple, who got married in 1999 and split in 2006, share kids Ava and Deacon.
Heath Ledger & Michelle Williams
The late Heath Ledger was all smiles when he walked the carpet at the 78th Annual Academy Awards in 2006 with his girlfriend Michelle Williams. The pair, who shared one child together, dated for three years before separating in 2007 just months before Ledger’s death.
Johnny Depp & Vanessa Paradis
Johnny Depp and Vanessa Paradis looked both cool and mysterious on the carpet at the 80th Annual Academy Awards in 2008. The pair, who share kids Lily-Rose and Jack, were together for 14 years before their split in 2012.
Heidi Klum & Seal
Heidi Klum and Seal were among our most fashionable couples at the 2008 Oscars. The former pair were married for seven years before separating in 2012.
Vanessa Hudgens & Zac Efron
Back in 2009, High School Musical alums Vanessa Hudgens and Zac Efron arrived in style at the Oscars. The pair broke things off in 2010 after four years of dating.
Jennifer Aniston & John Mayer
Jennifer Aniston and John Mayer made their Oscars debut at the Vanity Fair Oscar party in 2009. The pair dated for a year before their 2009 split.
Tom Cruise & Katie Holmes
Tom Cruise and Katie Holmes looked chic at the 2012 Vanity Fair Academy Awards Oscars Party.
The pair, who first started dating in 2005, got married in 2006 but announced their split years later in 2012.
George Clooney & Stacy Keibler
George Clooney and Stacy Keibler attended the 2013 Oscars hand in hand.
After two years of dating, Clooney and Keibler called it quits in July 2013.
Jennifer Garner & Ben Affleck
Jennifer Garner and Ben Affleck looked so sweet as they held hands at the 2013 Oscars red carpet.
The former duo, who tied the knot in 2005 and share three children together, called it quits in 2015.
Brad Pitt & Angelina Jolie
Brad Pitt and Angelina Jolie looked beautiful at the Oscars together in 2014.
In 2016, Jolie filed for divorce after only two years of marriage. The two share six kids together.
Diane Kruger & Joshua Jackson
Diane Kruger and Joshua Jackson arrived at the 2015 Vanity Fair Oscar Party in style. Less than a year later, however, the pair announced their split after ten years together.
Jennifer Aniston & Justin Theroux
Justin Theroux and Jennifer Aniston looked like the ultimate power couple at the 2015 Oscars. The exes ended up splitting in February 2018.
Jennifer Lopez & Alex Rodriguez
Jennifer Lopez and Alex Rodriguez looked so in love at the 2019 Academy Awards.
Sadly, however, the pair, who became engaged in March 2019, announced their split in March 2020.
Jason Momoa & Lisa Bonet
Jason Momoa and Lisa Bonet, who had been married since 2017, were one of our favorite couples on the 2019 Oscars red carpet before they announced their split in early 2022.
Bradley Cooper & Irina Shayk
At the 2019 Oscars, Bradley Cooper and Irina Shayk couldn’t keep their eyes off of one another.
Cooper and Shayk, who share 6-year-old daughter Lea, were together from 2015 to 2019.
Kim Kardashian & Kanye West
Kim Kardashian and Kanye West never made their way to the Oscars red carpet, but they did have this memorable photo opp at the Vanity Fair afterparty in 2020. The pair, who tied the knot in 2014, split in early 2021.
Paulina Porizkova & Aaron Sorkin
The short-lived but buzzy pairing of supermodel Paulina Porizkova and director Aaron Sorkin made their red carpet debut at the 2021 Oscars. The pair split up only a few months later in July.
Jodie Turner-Smith & Joshua Jackson
Joshua Jackson proved he was the perfect gentleman as he held his ex-wife Jodie Turner-Smith’s hand at the 2023 Vanity Fair Oscar Party. Despite the sweet PDA, however, the pair called it quits a few months later.
The pair, who started dating in 2018, share one daughter named Juno Rose Diana Jackson, born in April 2020.
Joe Jonas & Sophie Turner
In another one of last year’s shocking splits, Joe Jonas and Sophie Turner also attended the 2023 Vanity Fair Oscar. Jonas filed for divorce in September 2023 after four years of marriage. During their marriage, the pair welcomed two children together, daughters Willa and Delphine.
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