20 Years of Celebrity Couples

That glittering, shape-shifting phenomenon, the celebrity couple.

gwyneth paltrow and brad pitt
That glittering, shape-shifting phenomenon, the celebrity couple.
1 of 43
Celebrity Couples
Gwyneth Paltrow

1995: The toothsome twosome: with former fiancé BRAD PITT
M. Curtis/DMI/Time Life Pictures/Getty Images
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2 of 43
Celebrity Couples
Gwyneth Paltrow

1998: Perfecting the group hang with BEN AFFLECK
D. Alloca/DMI/Time Life Pictures/Getty Images
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3 of 43
Celebrity Couples
Gwyneth Paltrow

1999: GWYNETH PALTROW and SCOTT SPEEDMAN
Before going mum in London, the princess of priss was an It-boy magnet.
Everett Collection
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4 of 43
Celebrity Couples
Gwyneth Paltrow

2001: LUKE WILSON
Everett Collection
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5 of 43
Celebrity Couples
Gwyneth Paltrow

2002: Viva la Velveeta with CHRIS MARTIN
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6 of 43
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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7 of 43
Celebrity Couples
Angelina Jolie

1995: First husband JONNY LEE MILLER
FPIX/Bauer-Griffin
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8 of 43
Celebrity Couples
Angelina Jolie

1996: TIMOTHY HUTTON
R. Galella Ltd/Wire Image
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9 of 43
Angelina Jolie and Brad Pitt
2005: Angelina Jolie and BRAD PITT
George Pimentel/Wire Image
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10 of 43
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.
Duritz: Patti Ouderkirk/WireImage.com, Aniston: KMazur/WireImage.com
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11 of 43
Celebrity Couples
Jennifer Aniston

1996: TATE DONOVAN
M. Curtis/DMI/Time Life Pictures/Getty Images
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12 of 43
Celebrity Couples
Jennifer Aniston

1998: Tinseltown's prom king and queen holding court
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13 of 43
Celebrity Couples
Jennifer Aniston

2005: VINCE VAUGHN
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14 of 43
Celebrity Couples
Jennifer Aniston

2008: Round two with paparazzi pup JOHN MAYER
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15 of 43
Celebrity Couples
Cameron Diaz

1999: Special friend KELLY SLATER
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16 of 43
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.
SGranitz/Wire Image
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17 of 43
Celebrity Couples
1999: JARED LETO
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18 of 43
Celebrity Couples
Cameron Diaz

2008: Model boyfriend PAUL SCULFOR
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19 of 43
Celebrity Couples
Cameron Diaz

2003: Shoots, scores with JT
L. Blumenfeld/Getty Images
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20 of 43
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.
B. King/Wire Image
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21 of 43
Celebrity Couples
Jennifer Lopez

2001: BENNIFER heyday
K. Winter/Getty Images
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22 of 43
Celebrity Couples
Jennifer Lopez

1999: Hot shots with DIDDY
D. Alloca/DMI/Time Life Pictures/Getty Images
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23 of 43
Celebrity Couples
Jennifer Lopez

2002: With No. 2 CHRIS JUDD
K. Mazur/Wire Image
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24 of 43
Celebrity Couples
Jennifer Lopez

2004: MARC ANTHONY
Venturelli/Wire Image
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25 of 43
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.
S. Granitz/Wire Image
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26 of 43
Celebrity Couples
Drew Barrymore

1996: LUKE WILSON
M. Towski/DMI/Time Life Pictures/Getty Images
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27 of 43
Celebrity Couples
Drew Barrymore

2001: TOM GREEN
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28 of 43
Celebrity Couples
Drew Barrymore

2002: The Strokes' FABRIZIO MORETTI
K. Mazur/Wire Image
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29 of 43
Celebrity Couples
Drew Barrymore

2007: Mac'in with Apple's JUSTIN LONG
T. Williamson/WireImage
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30 of 43
Celebrity Couples
Salma Hayek

1999: SALMA HAYEK and OSCAR DE LA HOYA
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