Owen Wilson, Sheryl Crow(01 of40)
Open Image ModalJohnny Depp, Ellen Barkin(02 of40)
Open Image ModalLance Armstrong, Ashley Olsen(03 of40)
Open Image ModalRyan Gosling, Sandra Bullock(04 of40)
Open Image ModalRoger Ebert, Oprah Winfrey(05 of40)
Open Image ModalAndre Agassi, Brooke Shields(06 of40)
Open Image ModalNowadays, it's hard to imagine that one of the most high-profile couples in the '90s was tennis star Andre Agassi and actress Brooke Shields. The couple dated for six years before marrying in 1999; they divorced just two years later. (credit:Getty)
George Clooney, Talia Balsam(07 of40)
Open Image ModalWinona Ryder, Jimmy Fallon(08 of40)
Open Image ModalCourteney Cox, Michael Keaton(09 of40)
Open Image ModalHelen Hunt, Matthew Broderick(10 of40)
Open Image ModalConan O'Brien, Lisa Kudrow(11 of40)
Open Image ModalSarah Jessica Parker, Robert Downey Jr.(12 of40)
Open Image ModalDrew Barrymore, David Arquette(13 of40)
Open Image ModalThese two Hollywood staples were briefly linked in 1991 -- eight years before they starred together in 1999's "Never Been Kissed." (credit:Getty)
Carson Daly, Tara Reid; Katie Holmes, Chris Klein(14 of40)
Open Image ModalCutest -- and weirdest -- double date ever? Carson Daly/Tara Reid and Katie Holmes/Chris Klein are the epitome of the '90s here. (credit:Getty)
Moby, Natalie Portman(15 of40)
Open Image ModalAshton Kutcher, January Jones(16 of40)
Open Image ModalJack Nicholson, Lara Flynn Boyle(17 of40)
Open Image ModalGary Oldman, Uma Thurman(18 of40)
Open Image ModalJennifer Love Hewitt, Joey Lawrence(19 of40)
Open Image ModalScott Baio, Pamela Anderson (20 of40)
Open Image ModalEmilio Estevez, Demi Moore(21 of40)
Open Image ModalCameron Diaz, Matt Dillon(22 of40)
Open Image ModalThe telegenic "There's Something About Mary" co-stars dated for three years before splitting in 1998 -- the same year the hit comedy hit the big screen. (credit:Getty)
Macaulay Culkin, Mila Kunis(23 of40)
Open Image ModalMadonna, Dennis Rodman(24 of40)
Open Image ModalBilly Corgan, Tila Tequila(25 of40)
Open Image ModalThe romance between the Smashing Pumpkins frontman and the reality star came out of nowhere, and left just as quickly as it arrived. (credit:Getty)
Shia LaBeouf, Hilary Duff(26 of40)
Open Image ModalEmma Stone, Kieran Culkin(27 of40)
Open Image ModalJohn Stamos, Marlee Matlin(28 of40)
Open Image ModalWhoopi Goldberg, Ted Danson(29 of40)
Open Image ModalSean Lennon, Leelee Sobieski(30 of40)
Open Image ModalJohn Lennon's son and Sobieski were spotted canoodling during a Rock & Roll Hall Of Fame induction in 2004, when the former teen star was just 20 years old. (credit:Getty)
Jake Gyllenhaal, Natalie Portman(31 of40)
Open Image ModalRyan Reynolds, Kristen Johnson(32 of40)
Open Image ModalBefore Blake, before Scarlett, before Alanis, Reynolds dated yet another famous face: Kristen Johnston, of "Third Rock from the Sun" fame (pictured together here, in 1999). (credit:Getty)
Matthew Morrison, Kristen Bell(33 of40)
Open Image ModalEdward Norton, Courtney Love(34 of40)
Open Image ModalMinka Kelly, Donald Faison(35 of40)
Open Image ModalBefore she got together with Yankees star Derek Jeter, Kelly dated the "Clueless" actor for a year, from 2004-2005. (credit:Getty)
Brad Pitt, Robin Givens(36 of40)
Open Image ModalAl Pacino, Diane Keaton(37 of40)
Open Image ModalKeaton dated her "Godfather" co-star Al Pacino in the '80s; the relationship dissolved after Keaton pushed a marriage ultimatum on Pacino. She told People: "He's charming, hilarious, a nonstop talker. There was an aspect of him that was like a lost orphan, like this kind of crazy idiot savant. And oh, gorgeous! I was mad for him. I worked hard on that one." (credit:Getty)
Meg Ryan, Russell Crowe(38 of40)
Open Image ModalSeal, Tyra Banks(39 of40)
Open Image ModalSeal sure has a thing for telegenic supermodels! Seal and Tyra confirmed their budding romance when they stepped out to the Essence Awards in 1996, but broke up shortly thereafter. (credit:Getty)
Enrique Iglesias, Sofia Vergara(40 of40)
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