Drew Barrymore became a Guess Girl right around the time she was reviving her career as an actress. The then-18-year-old former child star appeared in a series of ads shot in 1993 by Wayne Maser. A few years later, she starred in "Boys on the Side" and "Mad Love," and she hasn't had much trouble since then. Barrymore, a fan of the romantic comedy, has added several to her résumé, including "The Wedding Singer," "Ever After," Woody Allen's "Everyone Says I Love You" and this year's "Music & Lyrics." With her production company, Flower Films, Barrymore has produced and starred in "Never Been Kissed," "50 First Dates" and the movie remake and sequel to the Seventies TV show "Charlie's Angels."

Claudia Schiffer first appeared in a Guess campaign in 1989. The sexy photographs, shot by Ellen von Unwerth, catapulted Schiffer's career and was a key step in her becoming a supermodel. She has more than 700 magazine covers under her belt and reportedly once appeared on five U.S. and seven European magazine covers simultaneously.

After the Guess campaign, she was chosen by Karl Lagerfeld to be the new face of Chanel, and she has landed in a slew of feature films, including "Love Actually," "Life Without Dick," "Black and White" and "Friends and Lovers." She has two children, Caspar and Clementine, with her husband of five years, film producer Matthew Vaughn.

Paris Hilton, the hotel heiress, posed for Ellen von Unwerth in 2004. Prior to the campaign, Hilton became a household name overnight after a sex tape was leaked on the Internet. Hilton went on to star in the movie "House of Wax" and the Fox reality TV show "The Simple Life," with Nicole Richie. Hilton is the founder of Heiress Records, a sublabel of Warner Bros. Records. Her album was released in August 2006 and made its debut at number six on the Billboard 200. Hilton's other business dealings include fragrances with Parlux, handbags with Samantha Thavasa, jewelry with Amazon.com, and the Club Paris chain of nightclubs.

Naomi Campbell was already an accomplished model when she became a Guess Girl. After landing on the covers of American, French and British Vogue and Time magazine, she signed on with Guess in 1991. Ellen von Unwerth shot Campbell with Eva Herzigova in Guess' signature black and white. Campbell has also appeared on the catwalk for virtually every major designer. She has acted in the films "Miami Rhapsody," "Girl 6" by Spike Lee and "Invasion of Privacy."

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