1 Thank God for Shakespeare In Love. Because until it came along, Gwyneth's biggest claim to fame was being known as Brad Pitt's ex. As for why they broke up, Gwyneth chalks it up to her youth. "He's sweet," she recently told Premiere magazine. "But when you're 22 years old... I didn't know anything about anything." 2 Another important benefit to making Shakespeare In Love… Gwyneth met and started going out with Ben Affleck. Their subsequent parting was so amicable, people doubted they ever really broke up. In fact, even though she began dating another eligible bachelor (see No. 3), Ben and Gwyn were very recently spotted once again acting, well… not like friends, but something a little more intimate. 3 Guy Oseary is one of the brains behind Madonna's Maverick record label, and her movie company, Mad Guy. He has also been linked with Fran Drescher and Renée Zellweger. 4 Jennifer Aniston and Brad Pitt seem to be edging closer to the altar. The two recently finished second on a list of the world's sexiest couples. The winners? Tom Cruise and Nicole Kidman. 5 Shoshanna created a stir when she began dating Jerry Seinfeld at age 18. (Jerry was 39.) After they split up, Shoshanna made a name for herself with her own brand of designer lingerie. Rumor has it that the vivacious beauty is now seeing Ben Affleck. 6 No, Madonna and Guy Oseary have never really been romantically linked. Their connection is purely professional. She's just his boss. 7 Ethan Hawke and Uma Thurman have been married since May of 1998. They have an 18 month-old daughter, Maya Ray. 8 Although rich beyond his dreams, Jim Carrey recently told Vanity Fair that he's quite lonely. He was said to be seeing actress Renée Zellweger, his costar in the upcoming comedy, Me, Myself and Irene. He's also been linked to Courtney Love, his costar in the Andy Kaufman bio, Man on the Moon. 9 Julia Roberts, the highest-paid woman in Hollywood, seems to have finally found her man - the very handsome Benjamin Bratt, ex of TV's Law & Order. But the number of Julia's former boyfriends makes forming this list a lot easier. 10 When Lara Flynn Boyle (29) and her boyfriend Jack Nicholson (62) were dining recently at a chic restaurant, a flower seller asked if Jack would like to buy a flower for his "granddaughter." The ruse got a big laugh, especially when it was learned that Danny DeVito put the flower girl up to it. 11 Matthew McConaughey loves women and loves to party. He was recently arrested for marijuana possession when a neighbor complained that he was playing his bongo drums naked with the windows open. No charges were laid. 12 Although Ed Burns is a movie director, his biggest claim to fame has come for his work as an actor - specifically his role in Saving Private Ryan. Ed's first notable flick, The Brothers McMullen, starred girlfriend Maxine Bahns. Then he was rumored to be dating his No Looking Back costar Lauren Holly. Lately, he's been linked with Heather Graham, star of The Spy Who Shagged Me. 13 Kyle McLachlan and Lara Flynn Boyle met on the set of the very strange early '90s TV hit, Twin Peaks. 14 Ashley Judd says the reason she doesn't date more is simply because she doesn't get asked. She's currently seeing race car driver Dario Franchitti. 15 Canadian-born supermodel Linda Evangelista and Kyle McLachlan were an item for some six years before their split last year.