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The son of writer, director, actress, and producer Polly Draper (thirtysomething) and musician Michael Wolff (the bandleader on The Arsenio Hall Show), Nat Wolff co-launched a band during his preschool years with his younger brother, Alex, christened the Naked Brothers Band. The outfit culled a considerable amount of commercial success that extended well into the boys' school years; it found Nat authoring and performing bubblegum pop songs, and Alex playing drums, with other youngsters lending added musical support. All told, the boys' precocious adventures prompted Draper to develop, write, executive produce, and direct a scripted feature for television, based on their exploits and starring her two young sons. Appropriately called The Naked Brothers Band Movie, it won the Audience Award at the 2005 Hamptons International Film Festival and gleaned legions of young fans for the up-and-coming musicians (particularly teen and preteen girls). Within a couple of years, the success of this initial effort led to a spin-off show on Nickelodeon, the mockumentary series The Naked Brothers Band (2007), which traveled behind the scenes of the group for a goofy, madcap view of the musicians' day-to-day antics. When the show commenced production, Nat was 11 years old, Alex 8.