Madonna & Michael Jackson
The King and Queen of Pop stunned on the red carpet at the 1991 Academy Awards. The gloved one was strictly Madge's plus-one, denying all rumors they were the next power couple.
Drew Barrymore & Edward Norton
The blonde pair dated briefly after filming Everyone Says I Love You. And they looked very in love when Barrymore accompanied Edward to the Oscars in 1999 when he was nominated for American History X.
Leonardo DiCaprio & Gisele Bündchen
Remember they dated? This gorgeous couple attended the 77th Academy Awards in 2005 just as their on-again, off-again love affair that began in 2000 was about to hit the skids.
Jennifer Aniston & John Mayer
The rumored duo put the speculation surrounding their coupling to rest when they finally made it official at the 2009 Oscars.
Jennifer Lopez & Ben Affleck
Bennifer was a dazzling duo at the 2003 Oscars, but their love affair soon ended when their wedding was postponed and eventually called off completely.
Gwyneth Paltrow & Brad Pitt
These Hollywood darlings met in 1995 on the set of Seven and although they walked the 1996 Oscars red carpet hand-in-hand, his asking for her hand in marriage never turned into wedded bliss.
Winona Ryder & Dave Pirner
The actress moved on from Slater to ex-fiancé Johnny Depp (who thought they'd be forever) before winding up with her Soul Asylum frontman boyfriend, who she brought to the 1995 Oscars.
Lauren Bacall & Humphrey Bogart
These legends of the big screen were a happily married couple with a 25 year age difference, but their love affair remained a secret at first. By the time the 1952 Academy Awards rolled around, the couple's high-profile romance was in full swing.
Diane Keaton & Steve Martin
The legendary actress paid controversy-stirring homage to Woody Allen at the 2014 Golden Globes, but in 1995 she showed up to the Oscars with her Father of the Bride funnyman costar.
Drew Barrymore & Tom Green
The unlikely couple married in 2000 and rocked the red carpet together that same year at the Oscars. They divorced the following year, but Barrymore has more than moved on and is now a new mom!
Winona Ryder & Christian Slater
The 80s megastars briefly dated after starring in Heathers together and made an appearance on the 1989 Academy Awards red carpet.
Angelina Jolie & James Haven
Jaws droppped when Angie and her brother kissed at the 2000 Academy Awards. She later said of the passionate PDA, "It was disappointing that something so beautiful and pure could be turned into a circus."
Ellen DeGeneres & Anne Heche
This year's Academy Award's host once walked the 1999 Oscars red carpet with her then girlfriend, who is now into men.
MORE PHOTOS: Check out Oscar gowns throughout the years!