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18 of Hollywood's Hit and Miss May-December Marriages

On the heels of Ashton Kutcher and Demi Moore divorce announcement, THR looks back at the couples with famously wide age gaps -- including the duos still making it work (Annette Bening and Warren Beatty) and the couples who just couldn't cut it (Billy Joel and Katie Lee).

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1 17

Ashton Kutcher and Demi Moore

Ashton Kutcher and Demi Moore
2 17

Warren Beatty and Annette Bening

Warren Beatty and Annette Bening
3 17

Billy Joel and Katie Lee

Billy Joel and Katie Lee
4 17

Nicolas Cage and Alice Kim

Nicolas Cage and Alice Kim
5 17

Maxwell Caulfield and Juliet Mills

Maxwell Caulfield and Juliet Mills
6 17

Tom Cruise and Katie Holmes

Tom Cruise and Katie Holmes
7 17

Michael Douglas and Catherine Zeta-Jones

Michael Douglas and Catherine Zeta-Jones
8 17

Clint Eastwood and Diana Ruiz

Clint Eastwood and Diana Ruiz
9 17

Harrison Ford and Calista Flockhart

Harrison Ford and Calista Flockhart
10 17

Kelsey Grammer and Kayte Walsh

Kelsey Grammer and Kayte Walsh
11 17

Doug Hutchison and Courtney Stodden

Doug Hutchison and Courtney Stodden
12 17

Padma Lakshmi and Salman Rushdie

Padma Lakshmi and Salman Rushdie
13 17

Larry King and Shawn Southwick

Larry King and Shawn Southwick
14 17

Donald and Melania Trump

Donald and Melania Trump
15 17

Bruce Willis and Emma Heming

Bruce Willis and Emma Heming
16 17

Woody Allen and Soon-Yi Previn

Woody Allen and Soon-Yi Previn
17 17

Zsa Zsa Gabor and Frédéric Prinz von Anhalt

Zsa Zsa Gabor and Frédéric Prinz von Anhalt

What do you think?

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