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After top-rated TV talk show host Bobby Bishop (Vincent Gallo) suffers a meltdown on the air, he leaves his show and heads to New York City to find his ex-girlfriend, Lily (Courteney Cox). But Lily isn't thrilled that Bobby gained fame and fortune without her, and she goes to great lengths to keep him at a distance. Director Justin McCarthy's independent romantic comedy co-stars Jeffrey Tambor and Tate Donovan as Lily's cross-dressing boyfriend.