Jennifer Aniston

In the late '90s, she also began dating actor Brad Pitt. Talk of Pitt's recently ended engagement to actress Gwyneth Paltrow quickly dissipated as "Gwen and Brad" turned to "Jen and Brad." The two young stars became the ultimate Hollywood power couple and celebrated with a star-studded wedding in July of 2000. The new millennium found Aniston at the top of her game. Raking in a million dollars an episode for her role on the still popular Friends and married to one of the hottest men in Hollywood, she seemed to have it all. Secure in her A-List position, she took the opportunity to work on low-profile films and cult hits, such as 1999's Office Space, and 2000's Rock Star. Aniston's talent for dramatic roles was finally given a proper outlet when she played the lead in 2002's The Good Girl, which found critics surprised and impressed with her range. She made no attempt to shy away from comedy, however, starring alongside Jim Carrey in Bruce Almighty, and Ben Stiller in 2004's Along Came Polly. In 2004, as Friends began what would be its final season, Aniston's immediate future was filled with tremendous turmoil and change. Only a week into 2005, she and husband Brad Pitt legally separated, surrounded by rumors that Pitt had sparked a serious romantic connection with his Mr. and Mrs. Smith co-star Angelina Jolie. The media leapt onto the story, desperate to sate the public's curiosity about how such a seemingly perfect union could come to an end. Rumors swilled about the circumstances of their break-up, citing everything from disagreements over children to taste in interior decorating. Aniston's steady poise and willowy figure created a division in the public perception between herself and the more curvaceous and risqué Jolie.
Media frenzy buzzed around the breakup long after she and Pitt officially filed for divorce in March. Vendors even started selling T-shirts reading "Team Aniston" and "Team Jolie," though most of the public seemed to side with the slighted Aniston. The actress plowed ahead, however, marking 2005 by starring with Clive Owen in the gritty thriller Derailed and with Shirley MacLaine and Kevin Costner in the comedy Rumor Has It.... 2006 brought the ensemble film Friends With Money, as well as another movie that would help put her divorce in the past...in more ways then one. While Pitt made headlines by becoming legal guardian of Jolie's adopted children and father to a baby Jolie gave birth to in Namibia, Aniston starred alongside comedy and character actor extraordinaire Vince Vaughn in The Break-Up. The comedy cast the two as an ex-couple going to war over which of them should keep their beloved condo, but the real life connection between the actors was quite the opposite. Though reluctant to speak about their relationship publicly, Aniston and Vaughn appeared quite clearly to have become a couple, bolstering the success of The Break-Up and pleasing fans who were relieved to see her happy. ~ Cammila Albertson, All Movie Guide