The 40 Biggest Celebrity Love Stories Of The '00s

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

celebrity best of decade

Over the last ten years, we've watched our favorite celebs hook up, break up, break down, flip out and start over. With all of its love triangles, legal battles, family dramas and political scandals, the "Naughties" certainly earned its wicked name!

1. The Jen/Brad/Angelina Triangle - Gossip bloggers should give daily thanks to the pop culture gods for Brad Pitt's and Jennifer Aniston's 2005 divorce. No other recent event has led to so much tabloid fodder. Despite their adulterous start, the tabloids quickly adopted "Brangelina" (and their million kids) as THE hip Hollywood couple, and Jennifer Aniston (against her will) became the post-child for lonely, single women everywhere.


2. Cruise and Kidman Call It Quits - Tom Cruise shocked fans—and Nicole Kidman—when he filed for divorced from his wife of ten years. Kidman revealed six weeks after the filing that she had suffered a miscarriage, fueling rumors that the baby may not have been Tom's. There were also whispers that the couple's inability to have a biological child and Kidman's unwillingness to convert to Scientology contributed to the split. Would you convert to Scientology for a man? What if it was Tom Cruise?

3. LiLo and SamRo: A Love Story - Serial man-dater Lindsay Lohan announced in a September 2008 email to the New York Post that she and DJ Samantha Ronson loved each other, and said in the December 2008 issue of Harper's Bazaar, "I think it's pretty obvious who I'm seeing." The relationship took a lot of crazy twists and turns, and finally ended in April 2009. Or did it? If rumors and Lindsay's tweets are to be believed, the two can't seem to quit each other, and have been on and off for months.


4. Kate Minus Jon Plus 8 - Before 2007 no one had heard of Jon and Kate Gosselin. Two years later, they were the tabloids' favorite train wreck. After their televised marriage hit the skids in 2009, with each one blaming the other and publicly airing all of their dirty laundry, all we could do was watch, opine and bask in the great cocktail of reality TV: a cool mix of schadenfreude and pity.

More Juicy Content From YourTango:

5. Britney and Kevin: Chaotic, Indeed - If Brad and Jen were Hollywood's Ken and Barbie, perhaps Britney and Kevin were Raggedy Ann and Andy? In 2004, Britney Spears announced that she was engaged to backup dancer-turned-rapper Kevin Federline, even though they'd only been dating for three months and Federline's ex, Shar Jackson, had just given birth to their second child. Brit-Brit and K-Fed married in September 2004, but after two years and two sons together, Spears filed for divorce. When Brit started acting crazy (remember the head-shaving incident?), Federllne won sole custody of the kids, with visitation rights for Spears.

6. Tom Cruise "Jumps the Couch" - May 23, 2005: A day that will live in infamy. Appearing on The Oprah Winfrey Show to talk about new ladylove Kaite Holmes, Tom Cruise made a scene by jumping up and down on Oprah's couch in a display that many viewers found contrived. Still, TomKat welcomed baby Suri in April 2006 and were married later that same year. So, maybe it's true love after all and the "marriage contract" rumors are just cynical gossip?


7. Anna Nicole's Baby Battle - When Anna Nicole Smith died in February 2007, several men claimed to be the father of her infant daughter Danielynn, including former bodyguard Alexander Denk, attorney/boyfriend Howard K. Stern and ex-lover Larry Birkhead (what a group of names!). Although Smith and Stern had both maintained that Stern was Danielynn's daddy, Birkhead demanded a paternity test. That April, a DNA test proved that Birkhead was the father.

8. Paul McCartney and Heather Mills Divorce - After marrying in 2002 and separating in 2006, Mills started talking crazy in 2007, saying that Paul's "evil" daughter Stella was to blame for their breakup, and that the Beatle had been emotionally and physically abusive. Things only got nastier from there, as Mills made a play for Paul's money and the tabloids gave the pair front-page press. The divorce was finalized in May 2008, at which point McCartney commented that he would have "peace at last."

9. Melissa Etheridge's Unlikely Sperm Donor - In 2000, Etheridge revealed to Rolling Stone magazine that aging rocker David Crosby was the biological father of her two children with then-partner Julie Cypher. Cypher gave birth to both babies, conceived via artificial insemination.

10. Eliot Spitzer's Sex Scandal - In 2008, we found out that New York Governor Spitzer had spent thousands of dollars on prostitues during his time as Governor and Attorney General. The disgraced "luv guv" resigned soon after the story broke. He escaped criminal charges when investigators found no evidence of misuse of public funds. Call girl Ashley Dupré, who received immunity for her testimony against Spitzer, enjoyed 15 minutes of fame, but she couldn't parlay that into a music career. Oddly enough, she recently became the New York Post's love advice columnist.


11. Britney's Quickie Marriage - In what is still possibly the shortest celebrity marriage ever, Britney Spears wed childhood friend Jason Alexander in 2004 at the Little White Wedding Chapel in Las Vegas. A mere 55 hours later, Spears annulled the marriage, citing that she and Jason didn't know each other well enough to get married.

12. Brad and Jennifer: The Perfect Couple? - In the first BIG wedding of the decade, Brad Pitt and Jennifer Anniston married on July 29, 2000 in an extravagant ceremony. Everyone thought the real-life Ken and Barbie would be together forever, but it was more like five years. Of course, in Hollywood, that's pretty close to forever.

13. John Edwards Cheats on His Wife - In 2008, the former vice presidential candidate admitted having an affair with campaign worker Rielle Hunter. Was the worst part that, at the time of the affair, Edward's wife was battling breast cancer? Or was the worst part that Edwards fathered his mistresses child, lied about it, and then spent campaign funds to cover it up?

14. Ellen DeGeneres and Anne Heche Break Up – Gossip lovers had always speculated about Heche's sexuality, so when the nutty actress split from Ellen in 2000 and married a man the following year, many believed that Heche had just been using DeGeneres to further her career.


15. Demi Moore's Happy, Extended Family - After a two-year courtship, Ashton Kutcher and Demi Moore tied the knot in 2005 surrounded by freinds and family, including Demi's ex-husband Bruce Willis, with whom she has three children. We continue to be amazed and impressed by how well the new and old husbands get along. The three stars often vacation together!

16. Angelina Jolie's Brotherly Love - Pre-Brad and Billy Bob, Angie weirded out the world at the 2000 Academy Awards when she announced in her acceptance speech that she was "so in love" with her brother Jamie Haven, whom she later was seen kissing. On the lips. For an uncomfortably long time. In fact, their kiss lasted longer than it took for the inevitable incest rumors to start.      

17. Britney, Christina and Madonna Pucker Up - Before Lindsay Lohan turned into a lipstick lesbian, before Katy Perry was kissing girls and liking it, and before Adam Lambert was simulating oral sex onstage, there was Madonna's infamous performance with Britney Spears and Christina Aguilera at the 2003 MTV VMAs. Their lingering girl-on-girl kisses had everyone else's tongues wagging too.

18. Britney and Justin Break Up - Friends since they were kids on The New Mickey Mouse Club, Britney Spears and Justin Timberlake ended their three-year, high-profile teen romance in 2002. Spears claimed she was devastated, but rumors of her infidelity abounded after the public saw Timberlake's video for "Cry Me a River."


19. Bennifer - When Jennifer Lopez left husband Cris Judd in 2002, she immediately began dating Ben Affleck. There wasn't a news program or tabloid that didn't analyze the glitzy relationship, and the intense media scrutinty may have caused their breakup. Just hours before their September 2003 wedding was to take place, Bennifer was no more. Both Jen and Ben went on to have successful marriages—and they'll always have Gigli.

20. Ellen DeGeneres Gets Married - When California's same-sex wedding ban was overturned in 2008, Ellen and her partner of four years, actress Portia de Rossi, got hitched that same summer. Since their wedding took place before the passing of Prop 8 in November, the union is still valid.

21. Rihanna Speaks Out Against Domestic Violence  - In June of 2009, R&B singer Chris Brown was sentenced to community service and five years' probation for assaulting his then-girlfriend Rihanna. Brown appeared on several news programs to express his regret over the incident, and Rihanna finally broke her silence on the issue in November, prior to releasing her successful new album, Rated R, in which she sings about the traumatic events. 

22. One Night in Paris - Previously famous for absolutely nothing, Paris Hillton reached mega-celebrity status when her night-vision sex tape with then-boyfriend Rick Salomon was leaked to the Internet in 2003. Hilton eventually won a percentage of the tape's sales profits, but she has claimed that she didn't keep any of the "dirty money."


23. Whitney Houston Gets Past Her Past - Married to bad boy Bobby Brown since the early '90s, good girl Whitney began the Naughties amid rumors of a drug addiction. The couple stayed together through Bobby's 2003 arrest for assaulting Whitney and the circus of their 2005 reality show, Being Bobby Brown, but Whitney finally filed for divorce in 2006. With her relatioship problems in her past, Houston has recently staged a musical comeback.

24. Four Is The Magic Number For Renee Zellweger And Kenny Chesney - After a four-month courtship, the actress and country singer married in May, 2005, only to split four months later. Zellweger filed for an annulment, citing "fraud" as the reason, which opened up the floodgates of speculation about Chesney's character and sexuality—because really, who wouldn't love Bridget Jones?

25. NASA Love Triangle - Former astronaut Lisa Marie Nowak was thrust into the international spotlight when she was arrested in 2007 for the attempted kidnapping of US Air Force Captain Colleen Shipman, the girlfriend of her former lover and fellow astronaut. Late night shows had a field day with the bizarre detail that Nowak wore adult diapers during her long drive from Houston to Orlando, even though Nowak denied that claim. What's the craziest thing you would do for love?

26. Girls Gone Wild - Teen pregnancy went under the microscope in 2008, when Britney Spears' 16-year-old sister Jamie Lynn had a baby. But the bigger shock was the discovery that Republican vice presidential candidate Sarah Palin's daughter Bristol was also with child. Although Sarah insisted that Bristol and her baby daddy Levi Johnston would marry, the two broke up a few months after the election. Levi and his "Johnston" went on to pose in "Playgirl". 


27. Robsten Mania - Teens and tweens (and some adults, if we're telling the truth) went nuts for Twilight in 2008, and gossip columnists' favorite pastime became speculating whether on-screen loves Robert Pattinson and Kristen Stewart were an off-screen couple. The Robsten rumors continue to this day, as does the Twilight hysteria.

28. David Letterman Extortion Attempt - On the October 1, 2009 episode of The Late Show, Letterman announced that someone tried to blackmail him with information that he'd had sex with female staff members. The gap-toothed funnyman admitted to the affairs, including one with former assistant Stephanie Birkitt, the ex-girlfriend of the extortionist, Joe Halderman. Letterman's on-screen apology diffused what could have been a much larger scandal, proving Letterman a savvy media-man—though not the savviest ladies man.

29. Call Tom Cruise Gay, He'll Make You Pay - In 2001, gay porn star Kyle Bradford (aka Chad Slater) allegedly told French magazine Actustar that he had an affair with Tom Cruise during his marriage to Nicole Kidman, and that her discovery of the relationship led to their divorce. Cruise ultimately won a $10M defamation suit against Bradford, who claimed that he never even gave the interview. Nonetheless, Cruse hasn't been able to shake the gay rumors—perhaps this has something to do with item six on this list?

30. Corey Clark, Fallen Idol - On this special 2005 edition of ABC's Primetime Live, former American Idol contestant Clark alleged that he had a three-month affair with kooky judge Paula Abdul during the 2003 season. Although the singer seemed to have quite a bit of evidence and witnesses to back up his claims, FOX stood behind Paula and the scandal quickly went away, as did Clark's album.


31. The Real Runaway Bride - In April 2005, Jennifer Wilbanks became an overnight celebrity when she claimed that she'd been kidnapped a few days before her wedding. It turned out that Wilbanks concocted the whole story, and that she had just run away due to cold feet. 

32. Tiger Woods: Golf's Biggest Womanizer - In November of this year, Tiger Woods suffered minor injuries in a car accident, amid rumors of marital problems. Speculation over Woods' wife's involvement in the wreck grew when it was discovered that Tiger had been having an affair  with at least one woman. Last time we checked, Tiger's mistress count was up to a whopping 13.

33. Madonna and Guy Ritchie End Marriage - The Material Girl surprised everyone when she wed director Guy Richie at the beginning of the decade. Eight years later, the pair divorced. Although Guy was set to receive something in the neighborhood of $80M in the settlement, he declined money in favor of shared custody of the couple's two children. Guy, you're not such a bad guy!


34. From Newlyweds To Newly Single - Soon after Jessica Simpson and Nick Lachey married, they starred in the MTV series Newlyweds: Nick and Jessica, which chronicled their life together, much of which included Nick's exasperation with his "dumb blonde" wife, a role that Jessica seemed to enjoy. The series ended in 2005, and the couple announced their separation soon after.

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.