Most Buzzed-About Oscar Dates of All Time

From Angelina and Cher to Natalie and Ben, see who floored Hollywood with their memorable plus-ones

01 of 10


Chris Carlson/AP

YEAR: 2009
When and Mayer showed up at the post-Oscars Vanity Fair party together, they finally confirmed what everyone already knew: They were a couple. But was this “outing” a coincidence or calculated move? That same night, Aniston’s ex, , would be making his first Oscar appearance with new flame (and Mr. and Mrs. Smith costar) .

Stay in the know about Jennifer Aniston by subscribing now.

02 of 10


Hector Mata/Reuters/Landov

YEAR: 2007
Someone couldn’t keep a secret. When BFFs and went to the Oscars together that year, both women looked stunning. Watts, wearing a buttercup yellow Escada empire-waist gown, was keeping mum about being five months pregnant with her and Liev Schreiber’s first baby. But in a major “oops” moment, the designer’s rep had spilled the beans in a pre-show press release, causing lots of “is she or isn’t she?” stares at Naomi’s belly.

Stay in the know about Nicole Kidman by subscribing now.

03 of 10


Kevin Mazur/WireImage

YEAR: 2005
For the ultra-private couple (who even kept their wedding a secret!), these two knew how to make a grand entrance! Looking like a throwback to old Hollywood glamour, dazzled in a slinky black velvet Versace gown and diamonds, while her debonair beau wore a classic tux for their Oscar red carpet debut.

Stay in the know about Beyoncé by subscribing now.

04 of 10


Bob Riha Jr/WireImage

YEAR: 2004
The normally reclusive turned up in a tux (!) and with Vanessa Paradis, his French actress-girlfriend, when he received his first Oscar nod, for Pirates of the Caribbean: The Curse of the Black Pearl. Seems that Depp was “double-dating” that night – he also brought along Betty Sue Palmer, his mom!

Stay in the know about Johnny Depp by subscribing now.

05 of 10


Kevin Winter/Getty

YEAR: 2003
By the time and , who met on the set of future bomb Gigli, walked the red carpet together, they were such a hot commodity, the press had dubbed them “Bennifer,” the first uni-name for a Hollywood supercouple. Though they broke off their engagement the following year, the glam duo kissed, cuddled and looked very much in love, much to the delight of fans on this Oscar night.

Stay in the know about Ben Affleck by subscribing now.

06 of 10


Gary Boas/Retna

YEAR: 2000
A kiss is just a kiss – unless it involves your brother. When – in Goth-inspired garb – planted one on the lips of bro James Haven during the Oscars pre-show, she cemented her reputation as a Hollywood wild card. Later, during her Best Supporting Actress acceptance speech for Girl, Interrupted, she went on to declare to him, “I’m so in love with you right now.”

Stay in the know about Angelina Jolie by subscribing now.

07 of 10


Time Life Pictures/Getty

YEAR: 1991
Tongues were wagging when , coming off her Blond Ambition tour and channeling Marilyn Monroe in Harry Winston diamonds and a white ermine stole, walked the red carpet with an equally flashy King of Pop dressed in a beaded jacket and crystal armband. Madge would later abandon her one-date wonder to work the stage and croon “Sooner or Later” from , which won for Best Song.

Stay in the know about Madonna by subscribing now.

08 of 10


Barry King/WireImage

YEAR: 1984
Before “cougar” referred to anything other than a jungle animal, 37-year-old Cher was sinking her teeth into 24-year-old unknown Val Kilmer. When he walked into the Dorothy Chandler Pavilion on the arm of the flamboyant singer, who was up for a Best Supporting Actress award for Silkwood, people noticed. The very next year he would film Top Gun.

Stay in the know about Cher by subscribing now.

09 of 10


Hulton Archive/Getty

YEAR: 1962
Considered one of Hollywood’s reigning beauties, Oscar nominee Natalie Wood brought her Splendor in the Grass costar (and notorious ladies’ man) Warren Beatty to the 1962 ceremony. The two were photographed laughing and looking happy. Shortly afterward, the actress filed for divorce from Robert Wagner, her husband of five years, and took up with her hunky costar.

Stay in the know about Warren Beatty by subscribing now.

10 of 10


Darlene Hammond/Getty

YEAR: 1961Theirs was the scandal heard ‘round the world. In 1958 Taylor’s then-husband, Mike Todd, was killed in a plane crash. His best friend, actor Eddie Fisher, comforted the grieving widow and, before long, left his wife Debbie Reynolds to marry Taylor. Fans were still in shock and awe at the sight of the new couple together at the 1961 Oscars, but Fisher proved to be Taylor’s good-luck charm: After three previous nominations, she finally won her first Academy Award, for Butterfield 8, that night.

Stay in the know about Elizabeth Taylor by subscribing now.

Related Articles