1. Jennifer Aniston/2. Brad Pitt, Y2K: When this picture was taken in February of 2000, Pitt and Aniston had been dating for roughly two years. Just a few months later, the two were married, a union that lasted until 2005, when the couple split and Pitt moved on to Angelina Jolie. The story was a tabloid dream come true, with lurid tales of Pitt, Jolie, and Aniston creating a soap opera storyline that's still being played out, nearly 5 years later: just this week, Star Magazine ran a cover declaring that Jennifer Aniston was finally ready for baby..."with Brad's help!"















