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Luke Wilson: Drew Barrymore
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Fresh off the success of their indie family flick, Wilson went on to play a co-worker with romantic designs on Calista Flockhart in "Telling Lies in America" (1997). That same year he completed a memorable cameo appearance in "Stab," the film-within-a-film of "Scream 2,†impersonating Skeet Ulrich's character from the original "Scream" (1996) to great comedic effect. Wilson found himself a viable leading man after appearing in "Best Men" and "Home Fries" in 1998 – two back-to-back romantic capers opposite Drew Barrymore, who became his real-life love in the midst of filming the latter. Both films were the kind of odd independents for which Wilson would become known. "Best Men" chronicled a heist that is performed on the way to a wedding, while "Home Fries" told the story of a man (Wilson) who falls for his late stepfather's pregnant girlfriend (Barrymore), whom he is meant to kill. Neither was a hit, with the Barrymore-Wilson coupling earning more notice than the films themselves.
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After large roles in three 1998 comedies, Bongwater, Home Fries, and Best Men (the latter two co-starring Barrymore), Wilson went on to star in another three comedies the following year. The first, Dog Park, was a Canadian film directed by Kids in the Hall alum Bruce McCulloch and featured Wilson as one of a group of twenty-somethings undergoing the trials and tribulations of love. Blue Streak starred the actor as the sidekick of robber-turned-policeman Martin Lawrence, while Kill the Man (which premiered at the 1999 Sundance Festival) cast him as the owner of a small copy center competing with a large chain store across the street.
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Despite the fact that Luke was a relative unknown at this point, he still managed to snag a famous girlfriend, Drew Barrymore. The two dated in 1997 and 1998, and they were co-stars in two movies during that time -- Best Men and Home Fries.
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Breaking up is hard to do for Luke Wilson. According to Page Six, the My Super Ex-Girlfriend star recently told Howard Stern: “Even if I want out, I don’t have the guts to just leave.†The actor, who was a guest on Stern’s Sirius Satellite Radio show, has a roster of exes that includes Gwyneth Paltrow, and Drew Barrymore.
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