'"[14] By age five, Wolff had started writing his own songs, and by the time he was in preschool, he constructed a band called The Silver Boulders with his best friends.

[6] Nat first gained notice in the wake of the September 11 attacks when he held his birthday party outside his apartment, which is where he performed his composition titled "Firefighters".

The benefit concert was a success; it raised over $46,000 and was donated to the children of New York City Fire Department's Squad 18.

As a result, Draper decided to appease Nat by letting him film his own sitcom called Don't Eat Off My Plate, which served as the basis for The Naked Brothers Band: The Movie.

[17] From the beginning, they were hesitant to expose Nat and Alex to stardom at a young age[18] and later agreed to the series spin-off on the provision that filming would take place only during the summers, which allowed him and his brother to proceed with their enrollment at private school in New York City.

The film was bought by a former Nickelodeon executive as the pilot to the television series of the same name (2007–09),[6][21] which was created, showran, written, and directed by his mother, while his father co-starred and produced and supervised the music.

The show produced two soundtrack albums and the single "Crazy Car" reached #83 on the Top 100 Billboard Charts.

Writing for Variety, critic Justin Chang stated: "Wolff, who's present in just about every scene, manages to hold the center as a young man who isn't overly concerned about either standing out or fitting in, and whose behavior can often be as hesitant as it is impulsive.

"[25] He starred in the off-Broadway revival of Sam Shepard's play Buried Child with Ed Harris and Taissa Farmiga, from February 2 through March 13, 2016.

[26] In 2017, Wolff starred in Death Note, a Netflix film based on the manga of the same name,[27] and the romantic comedy Home Again.