Hollywood is full of hits and misses — and none of them are more fascinating than the personal relationships celebrities engage in. Let’s travel back to the late ‘90s and ‘00s when celebrity trainwreck relationships were the dreams tabloid headlines were made of.
Pamela Anderson and Tommy Lee
John Mayer and Jessica Simpson
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Whoopi Goldberg and Ted Danson
Drew Barrymore and Tom Green
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Jude Law and Sienna Miller
Sandra Bullock and Jesse James
Carson Daly and Tara Reid
Ben Affleck and Jennifer Lopez
Kevin Federline and Britney Spears
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Tori Spelling and Dean McDermott
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Sammi Giancola and Ronnie Ortiz-Magro
Elin Nordegren and Tiger Woods
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Denise Richards and Charlie Sheen
Amy Winehouse and Blake Fielder-Civil
Lindsay Lohan and Samantha Ronson
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Sophia Bush and Chad Michael Murray
Nick Carter and Paris Hilton
Angelina Jolie and Billy Bob Thornton
Heidi Montag and Spencer Pratt
Aaron Carter and Hilary Duff
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