Celebrity Couples From the Past They Dated?! Celebrity Couples From the Past! February 13, 2013 Share This link Celebrity Couples From the Past Source: Getty 2 / 69 by Lauren Turner 13 Save 0 Favorite 0 Angelina and Billy Bob Angelina Jolie and Billy Bob Thornton met in 1999 while filming Pushing Tin and were married in 2000. They divorced in 2002 with Angelina taking custody of their newly adopted son, Maddox. More Photos Previous 2 / 69 Next by Lauren Turner 13 What’s Your Reaction? 0 0 0 0 0 0 Angelina and Billy Bob Angelina Jolie and Billy Bob Thornton met in 1999 while filming Pushing Tin and were married in 2000. They divorced in 2002 with Angelina taking custody of their newly adopted son, Maddox. 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Create one now! ewalsh 41 weeks Great blast from the past. Juiceee 1 year I had no idea January Jones and Josh Groban ever dated. annie6417 1 year OMG!!! It's so funny and wierd as well, especially to see Brad Pitt, Matt Dammon and Heath Ledger...!!! kimmieb124 1 year I actually thought Katie Holmes and Chris Klein were a good match. Much more appropriate for who she was up until Tom Cruise came into the picture. They seemed sweet together. But Christina Applegate and Brad Pitt??? What? I missed that one. curLRocker 1 year Alanis and Ryan?! Mind BLOWN. chocolate79 1 year some of this is just very funny.... matt damon and winnona ryder! ha.. that's old school jmhendricks88 1 year I used to love Jake Gyllenhaal and Kirsten Dunst together. They were so cute! popfaninMD 1 year ahhhhhhh. Popsugar is going THERE....LOL...Madonna and Sean Penn, Crusise and Cruz....Ahhh what could have been. I'm particularly fascinated you included Garner and Varten. I thought was buried in a vault some where. LOL noonehere 1 year Colin and Busy??? ah ah ah! (terrible 90's or early 00's) ModernGraceKelly 1 year I remember Sandra and Ryan, because they did a movie together. He seems to date his leading ladies. I knew most of them, but some surprised me. I had no idea Edward Norton was engaged to Courtney Love. I just thought they went on a few dates. dreamalittledream 1 year wow brad really takes on the style of whoever he's dating! He and Gwyneth look like twins!!! (Whether he's dressing like Gwyneth, a California/beach style or motorcycle man, he always looks good though!) Allie Merriam 1 year Each couple is more surprising than the last! Anna Monette Roberts 1 year Really funny and freaky! 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