The 40 Biggest Celebrity Love Stories Of The '00s

celebrity best of decade

We take a look back at Brangelina, Bennifer, and the 00s' most unforgettable celebrity love stories.


35. Who Wants To Marry A Multi-Millionaire? - Darva Conger did...until she got to know her new husband, Rick Rockwell, whom she married on the February, 2000 FOX special. After discovering that Rockwell had been accused of domestic violence and was more of a multi-thousandaire, Conger had the marriage annulled in April 2000. And then, of course, she posed for Playboy.

36. Alec Baldwin and Kim Basinger Get Dirty - After an eight-year marriage, the two actors filed for divorce in 2001. Their nasty custody battle over daughter Ireland became public in 2007, when the media released a taped voicemail message (possibly leaked by Basinger) in which the irate Alec bashed Kim and called his 11-year-old child a "thoughtless little pig."

37. Laying Down With Jude Law - In 2005, Jude publicly apologized for cheating on fiancée Sienna Miller with his children's nanny. Jude and Sienna tried to maintain their relationship, but ended things in 2006. Jude found himself the subject of gossip again in 2009, after it was reported that he fathered a child with a one-night stand. Sienna made headlines also as Balthazar Getty's "other woman", but she and Jude seem to have found thier way back to eachother.

38. Angelina Jolie and Billy Bob Thornton's Weird Relationship - The two actors met while filming 1999's Pushing Tin and married in 2000. Angelina and Billy Bob quickly became tabloid favorites due to their odd behavior, including wearing vials of each other's blood around their necks and sexing it up in a limo on the way to an awards show. But not even blood and sex could keep them together; the pair divorced in 2003.

39. Elizabeth Hurley's Baby Daddy Woes - After giving birth to a son in spring 2002, Liz revealed that the father was British producer Stephen Bing. Bing denied paternity, stating that the couple's relationship was "non-exclusive," but a DNA test soon proved that Bing was the father. Although Bing agreed to take financial responsibility for his son, Hurley said his money was "not wanted or welcome." You go, girl.

40. Tom Green and Drew Barrymore's Five-Month Marriage - This unlikely pair got engaged in 2001, and when Green hosted Saturday Night Live that November, he told the audience that they would get married at the end of the show. When Barrymore decided not to go through with it, fans began to wonder if the whole relationship was one big prank. The couple finally tied the knot in July of 2001, but divorced that December.