20 Years of Celebrity Couples

That glittering, shape-shifting phenomenon, the celebrity couple.
gwyneth paltrow and brad pitt
M. Curtis/DMI/Time Life Pictures/Getty Images
That glittering, shape-shifting phenomenon, the celebrity couple.
gwyneth paltrow and brad pitt
M. Curtis/DMI/Time Life Pictures/Getty Images
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Celebrity Couples
Gwyneth Paltrow

1995: The toothsome twosome: with former fiancé BRAD PITT
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gwyneth paltrow and ben affleck
D. Alloca/DMI/Time Life Pictures/Getty Images
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Celebrity Couples
Gwyneth Paltrow

1998: Perfecting the group hang with BEN AFFLECK
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angelina jolie and jenny shimizu
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Celebrity Couples
Angelina Jolie

1994: JENNY SHIMIZU
Pre-sainthood, she humped in limos, smooched her bro, and accessorized with vials of blood.
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angelina jolie and timothy hutton
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Celebrity Couples
Angelina Jolie

1996: TIMOTHY HUTTON
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angelina jolie and brad pitt
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Angelina Jolie and Brad Pitt
2005: Angelina Jolie and BRAD PITT
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jennifer aniston and adam duritz
Duritz: Patti Ouderkirk/WireImage.com, Aniston: KMazur/WireImage.com
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Celebrity Couples
Jennifer Aniston

1995: JENNIFER ANISTON and ADAM DURITZ
When not playing the third wheel (thanks, Courteney!), the hair apparent is on the hunt for love and flatirons.
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jennifer aniston and tate donovan
M. Curtis/DMI/Time Life Pictures/Getty Images
11 of 34
Celebrity Couples
Jennifer Aniston

1996: TATE DONOVAN
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jennifer aniston and brad pitt
M. Curtis/DMI/Time Life Pictures/Getty Images
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Celebrity Couples
Jennifer Aniston

1998: Tinseltown's prom king and queen holding court
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cameron diaz and matt dillon
SGranitz/Wire Image
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Celebrity Couples
Cameron Diaz

1996: THERE'S SOMETHING ABOUT MATT DILLON
Forget those insane-with-jealousy rumors: She's the quintessential guy's gal — golfing, surfing, and kicking it courtside.
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cameron diaz and jared leto
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Celebrity Couples
1999: JARED LETO
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cameron diaz and justin timberlake
L. Blumenfeld/Getty Images
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Celebrity Couples
Cameron Diaz

2003: Shoots, scores with JT
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jennifer lopez and ojani noa
B. King/Wire Image
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Celebrity Couples
Jennifer Lopez

1997: FLY GIRL WITH HUSBAND NO.1 OJANI NOA
Old-school Jenny hopped around in pairings that promised more publicity than longevity.
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jennifer lopez and ben affleck
K. Winter/Getty Images
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Celebrity Couples
Jennifer Lopez

2001: BENNIFER heyday
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jennifer lopez and diddy
D. Alloca/DMI/Time Life Pictures/Getty Images
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Celebrity Couples
Jennifer Lopez

1999: Hot shots with DIDDY
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jennifer lopez and chris judd
K. Mazur/Wire Image
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Celebrity Couples
Jennifer Lopez

2002: With No. 2 CHRIS JUDD
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jennifer lopez and marc anthony
Venturelli/Wire Image
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Celebrity Couples
Jennifer Lopez

2004: MARC ANTHONY
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drew barrymore and eric erlandson of hole
S. Granitz/Wire Image
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Celebrity Couples
Drew Barrymore

1995: DREW BARRYMORE POLLINATING WITH ERIC ERLANDSON OF HOLE
With two quickie unions and a slew of flings, the boho butterfly floats from young studs to hapless duds.
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drew barrymore and luke wilson
M. Towski/DMI/Time Life Pictures/Getty Images
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Celebrity Couples
Drew Barrymore

1996: LUKE WILSON
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drew barrymore and tom green
D.Hogan/Getty Images
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Celebrity Couples
Drew Barrymore

2001: TOM GREEN
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drew barrymore and fabrizio moretti
K. Mazur/Wire Image
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Celebrity Couples
Drew Barrymore

2002: The Strokes' FABRIZIO MORETTI
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drew barrymore and justin long
T. Williamson/WireImage
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Celebrity Couples
Drew Barrymore

2007: Mac'in with Apple's JUSTIN LONG
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salma hayek and oscar de la hoya
SGranitz/Wire Image
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Celebrity Couples
Salma Hayek

1999: SALMA HAYEK and OSCAR DE LA HOYA
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