Did you know that, before he was married to Sarah Jessica Parker, Matthew Broderick was paired up with Helena Bonham Carter at the Oscars? How about Edward Norton's date to the 1999 Oscars, when he was nominated for best actor? The Academy Awards red carpet is always an opportunity for the brightest stars of the moment to look their best, but sometimes it's also a glimpse into surprising relationships, burgeoning friendships, or just two people you never quite expected to get so cozy in front of cameras. Whether it's power couples from the '70s you may have forgotten, or unexpected BFFs from the late '90s, these are our favorite surprising pairs from Oscars of the past.
Vanity Fair: The Surprising Oscar Couples You've Probably Forgotten
Nicholson was nominated at the 1971 Oscars for his role in Five Easy Pieces; he began dating Phillips, a member of the Mamas and the Papas, when she auditioned for a role in Mike Nichols’ Carnal Knowledge, released that year. The two remained a couple until 1974.
Reynolds and Shore met when he was a guest on her talk show in 1971, not longer after he filmed Deliverance. In a 1974 profile in People magazine Reynolds said he could be “flippant” about his career but not the “precious” relationship with Shore, who was 19 years his senior and reportedly told a friend, “I don't want to grow old in his arms." The two split in 1977. Reynolds told Larry King in 2000 “I wanted to marry her, I really did,” and that they remained close until her death in 1994.
When promoting her book in 2008 Bertinelli revealed that she met Spielberg when auditioning for Raiders of the Lost Ark, “which I was so wrong for.” In the book she continued, “We knew it was a fling. We had too many differences, including age, career status and religion. I met his mother, and I knew he wasn't going to marry someone who wasn't Jewish.” Bertinelli married Eddie van Halen the next year, in 1981, while Spielberg went on to marry his Temple of Doom star Kate Capshaw.
Shields was 15 and Jackson was 22 at the 1981 Oscars; writing about their relationship in Rolling Stone in 2009, after Jackson’s death, Shields said, “Everybody was always confused by our relationship. Nobody got it, and I didn't really care. [. . .] From the time we met when I was 13, we understood each other and became very good friends, and that was it.”
Not only was Kilmer Cher’s date to the 1985 Oscars, but it was Oscar royalty that brought them together—the couple met at a birthday party thrown for Cher by her Silkwood co-star Meryl Streep. In a People magazine profile a year before these Oscars, Cher described their first kiss: “I thought my head would shoot right off my body. I had to catch my breath."
Before they each became half of mega-famous celebrity couples, Broderick (later married to Sarah Jessica Parker) and Carter (later married to Tim Burton) teamed up to present the award for best documentary, short subject, at the 1987 Oscars. They were not, sadly, a couple in real life. Carter spoke out about her outfit in a 1999 interview: “ I remember journalists asking me who I was wearing. They wanted to know the name of the designer. I just said, 'The skirt's from my mum.'"
Slater and Ryder were iconic co-stars in 1988’s Heathers, but Slater claims he never even confessed the crush he had on her at the time. He told The Guardian in 2013, “As I've gotten to know myself over the years I realized I'm kind of a sweet, sensitive guy, a shy guy, and communication is not something I'm so good at.”
As she revealed to us recently, Parker was wearing a dress picked up from a Pittsburgh dressmaker, and even did her own makeup, for the 1989 Oscars, which she attended with Downey Jr.; in her words, “we were courting at the time.” They dated until 1991.
Roberts was celebrating her first Oscar nomination, for best supporting actress in Steel Magnolias, and dating Sutherland, her co-star in Flatliners. The two announced their engagement later that year, but broke it off the following summer.
The official archival caption for this photo describes Jackson and Madonna as “popular American singers,” which strikes us as a massive understatement—they may have been the most famous people on the planet at the time. In 2009 Madonna described their relationship in Rolling Stone: "So that's what we were doing: watching movies, having dinner, hanging out, going to the Oscars, being silly, seeing if we could work.”
Pitt and Lewis, co-stars in 1993’s Kalifornia, dated for four years. Lewis admitted in 2010 that she still gets questions about their relationship: “It amazes me that people are still fascinated that we went out for four years. I was a teenager at the time. It's a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy.”
Norton and Barrymore were close enough pals that she was picked to interview him in 1996, after they co-starred in Woody Allen’s Everybody Says I Love You. Barrymore accompanied Norton to the 1999 Oscars, when he was nominated for best actor for American History X, but if the two in fact ever dated, they never acknowledged it.
No, Liv Tyler and Drew Barrymore never dated either—Tyler was dating her future husband Royston Langdon at the time—but they were close enough pals to pose for this attention-grabbing photo at the 1999 Oscars.