The son of writer, director, producer, and actress Polly Draper (of thirtysomething fame) and musician Michael Wolff (the bandleader on The Arsenio Hall Show), Alex Wolff revealed prodigious musical talent during his preschool years, when he co-formed a rock act, the Naked Brothers Band, with older brother Nat Wolff. Within the band, Nat wrote and performed songs and Alex took to the drums; thanks in no small part to Draper's guidance and encouragement, the group parlayed its abilities into a considerable amount of commercial success. Meanwhile, Draper scripted, directed, and executive produced a made-for-television feature based on the boys' adventures and starring Nat and Alex, The Naked Brothers Band Movie. The film netted the Audience Award at the Hamptons International Film Festival in 2005 and spawned a mockumentary series on Nickelodeon, the 2007 The Naked Brothers Band. First produced when Alex was 8 years old and Nat 11, the program journeyed behind the scenes of the group for a goofy, farcical glimpse of the musicians' exploits.