As the process of making low-budget digital-video movies keeps getting easier, the old song from Gypsy keeps getting truer: Would-be directors gotta have a gimmick if they're going to stand out in an increasingly crowded field. As trivial as the micro-budget documentary My Date With Drew may seem, it has novelty on its side, and even when that flags, it coasts along on sheer personality. In a gimmick every bit as goofy as Morgan Spurlock's fast-food binge in the stylistically similar Super Size Me, unemployed 27-year-old "ordinary guy" Brian Herzlinger decides to spike $1,100 in game-show winnings into his lifelong dream: scoring a date with Drew Barrymore. ("Why Drew Barrymore?" he asks early on. "Because it's Drew Barrymore.") Using a single DV camera purchased from Circuit City, he and his friends begin documenting his efforts to meet Barrymore within 30 days, so they can return the camera before the refund window expires.
Like Spurlock with Super Size Me, or Paul Provenza with The Aristocrats, Herzlinger and his co-director buddies keep My Date With Drew light and lively with self-effacing, unselfconscious humor and creative variations on the central theme. Herzlinger visits a psychic for predictions about his success, and he enlists a Barrymore look-alike for a videotaped "test date," so his buddies can mercilessly dissect his dinner behavior. He seeks out advice from any available source, getting encouragement and discouragement along the way: His mom steadfastly declares that he'll probably succeed, but he shouldn't start a long-term relationship, because Barrymore is a slut, while TV director Bill D'Elia tells him that with this project, "the dumbing of America is complete," and jovially wishes him failure.
But mostly, Herzlinger just tries to climb the shaky "six degrees of separation" ladder, pursuing Barrymore through such comically tenuous connections as Corey Feldman, who dated her for a couple of months in the '80s. In the process, Herzlinger comes across as kind of a nebbishy Everyman, except funnier, luckier, and in possession of the most tolerant, supportive friends on the planet. His quest is amateurishly filmed (though slickly assembled) and self-indulgent, devoid of the larger perspective Michael Moore brought to bear on his similar efforts to meet GM CEO Roger Smith in Roger & Me, but Herzlinger doesn't seem to care. He's having fun, and he's willing to let the whole world play the game with him. My Date With Drew opens with a quote from Barrymore: "If you don't take risks, you'll have a wasted soul." Ultimately, though, the film says less about the veracity of this vague fortune-cookie motto than it says about how much America loves celebrity, chutzpah, and a good underdog story. In the right combination, those elements may always be a winning novelty.