By Wonderwall.com Editors
8:34am PST, Jan 23, 2020
The Oscars would make a perfect date night, but not everyone is lucky enough to attend with an invited guest. In celebration of the 2020 Academy Awards on Feb. 9, Wonderwall.com is taking a look back at the most memorable Oscar dates who still stand out… Starting with Cindy Crawford. You could say the model felt like a pretty woman when she attended the 63rd Annual Academy Awards in 1991 on the arm of then-boyfriend Richard Gere.
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Remember when Jennifer Aniston dated John Mayer? John even spoke to Ryan Seacrest about how he was nervous about going to the 81st Annual Academy Awards with his girlfriend. "It's not my world, the Oscar thing," he said on Ryan Seacrest's KIIS-FM radio show on Feb. 25, 2009. "You can go from a Grammy winner to a water boy when you walk in the Kodak Theatre on Oscar night," he added. "That's just like a whole different level." He also said that he went for "moral support," as Jennifer was there as a presenter.
Gwyneth Paltrow and Brad Pitt looked like Hollywood royalty when they arrived at the 68th Academy Awards in 1996 (they got engaged nine months later). In January 2015, Gwyneth reflected on the failed relationship on Howard Stern's SiriusXM radio show. "I definitely fell in love with him," she recalled. "He was so gorgeous and sweet. I mean, he was Brad Pitt!"
Angelina Jolie took brother James Haven to the 72nd Annual Academy Awards in 2000, and he was one of her most memorable dates ever: Remember when she kissed him on the lips that year?
Elizabeth Taylor walked the 1961 Academy Awards red carpet with then-husband Eddie Fisher. She took home the best actress Oscar that night and the following year started an affair with Richard Burton on the set of "Cleopatra."
In 1989, teenagers Drew Barrymore and Corey Feldman attended the 61st Annual Oscars together. It's hard to believe they briefly dated!
Arguably the world's biggest stars at the time, Madonna and Michael Jackson, caused quite a stir when they showed up at the 1991 Academy Awards together. "Michael was like, 'Well, who are you gonna go with?' I looked at him and said, 'I don't know. You wanna go?' And he said, 'Yeah, that'd be great,'" Madge told reporters. "And then, yes, he took me home. You wanna know what happened after that? I'm not gonna tell you." She later called MJ her "best date ever" in a post on Instagram.
Ellen DeGeneres and then-partner Anne Heche took their relationship public at the 71st Annual Oscars in 1999. The pair had met at an Oscar party two years earlier.
Hugh Grant brought model-actress Elizabeth Hurley to the 67th Oscars in 1995. The two had been dating since 1987 but split in 2000. "He is annoying," she told "Access Hollywood" in March 2015. "But I annoy him too. I mean, it's a mutual annoyance. But we love each other a lot."
Julia Roberts couldn't have looked happier at the 2001 Academy Awards, where she took home the best actress Oscar with then-boyfriend Benjamin Bratt by her side.
Angelina Jolie made the ultimate fashion statement (the infamous leg pose!) with then-husband Brad Pitt by her side at the 2012 Academy Awards.
Bradley Cooper isn't the only star who's brought his mom to the Academy Awards. But his mother, Gloria Campano Cooper, was certainly the most adorable mom on the red carpet at the 2013 Oscars in her pink, feathery sleeves and that look of pride on her face as she held her son's hand.
Best big sister ever? Lupita Nyong'o brought brother Peter Nyong'o Jr. to the 86th Oscars in 2014. Peter even ended up in the famous Ellen DeGeneres audience selfie that year.
Ben Affleck and Matt Damon's mothers were good luck charms at the 1998 Academy Awards. The longtime friends and first-time nominees won the best screenplay Oscar for "Good Will Hunting" with their proud moms, Chris Affleck and Nancy Carlsson-Paige, looking on.
Hollywood icons Humphrey Bogart and Lauren Bacall were inseparable at the 1952 Academy Awards, where Humphrey won for best actor. They were together until Humphrey's death in 1957.
Cher dazzled at the 1973 Academy Awards, which she attended with then-hubby Sonny Bono. The musical duo split two years later.
Joanne Woodward and Paul Newman were newlyweds when they attended the 1958 Academy Awards together. Joanne walked away with the best actress Oscar that night. They deeply devoted couple remained married for 50 years until Paul's death in 2008.
Heath Ledger and Michelle Williams looked picture perfect together at the 2006 Academy Awards, where both were nominated for their acting work in "Brokeback Mountain." The couple, who'd welcomed daughter Matilda just a few months earlier in 2005, called it quits the following year shortly before his death from an accidental drug overdose.
Laura Dern shared her red carpet spotlight with dad Bruce Dern at the 87th Annual Academy Awards in 2015. "I was 7," Laura told Ryan Seacrest of her first Oscars experience. "I came with my mother [Diane Ladd], who was nominated for [the] Scorsese film 'Alice Doesn't Live Here Anymore.' And I was as terrified as my children probably feel right now, who are here with me and their grandfather tonight." Laura was nominated in 2014 for best supporting actress for her work in "Wild," and her father was nominated the year before for his performance in "Nebraska." Between Laura and her parents, there are seven Oscar noms in the family!
Oprah Winfrey and her fiancé, Stedman Graham, looked glamorous at the 1987 Academy Awards, which they attended hand in hand. They're still together more than three decades later though never did get married.
Despite rumblings of relationship strife at the time, Bradley Cooper and Irina Shayk stepped out together at the 91st Annual Academy Awards on Feb. 24, 2019. It was a big night for Bradley's movie "A Star is Born" and his model girlfriend was along for the ride. But less than three months later, the couple called it quits.
