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He is the brother and bandmate of Nat Wolff in The Naked Brothers band.
His film roles include Hereditary, Dude and Jumanji: Welcome to the Jungle.
Troop Mom (2009), the romantic comedy New Year's Eve (2011), and the independent comedic drama Peace, Love & Misunderstanding (2011).
In 2010, he starred in his brother's play What Would Woody Do? Wolff co-starred in the comedy film Admission (2013), Palo Alto (2013), and the comedy film Behaving Badly (2014).
He acted alongside Jonah Hill in the 2011 comedy The Sitter.
His mother is actress and screenwriter Polly Draper.
He gained recognition for composing the music for The Naked Brothers Band (2007–2009), a Nickelodeon television series he starred in with his younger brother Alex that was created by their actress mother Polly Draper.