The siblings' musical efforts were initially discovered during their work on the Nickelodeon television series The Naked Brothers Band, which was created and produced by their mother, actress Polly Draper.
As recalled by the boys' mother, actress Polly Draper (star on ABC's Thirtysomething), Nat and Alex were infants when they arose from a bath proclaiming, "We're the naked brothers band!
"[1][2][3] After the September 11 attacks, six-year-old Nat composed the song "Firefighters" for a benefit he performed with his band, staged behind his Lower Manhattan apartment.
At first, she refused by explaining that it would be too difficult, so she made a compromise with Nat; in 2003, she let him film his own sitcom titled Don't Eat Off My Plate.
[1] During summer 2004, the film took production at the family's real-life apartment and throughout New York City,[2] at which time Nat was 9 and Alex was 6-and-a-half.
[1] Draper wrote and directed The Naked Brothers Band: The Movie, which was designed as an independent family project with a budget under $1,000,000.
[2] The film consisted of celebrities who were friends with Draper and Wolff, including Cyndi Lauper, Julianne Moore, Ann Curry, Uma Thurman, Tony Shalhoub, Ricki Lake, Arsenio Hall, and the complete cast of Thirtysomething.
Tom Asheim, the vice president and general manager of Nickelodeon said: Eventually, the staff at Nickelodeon persuaded Draper to put together a television series after comprising with short, 13 episode seasons over the summer and early autumn, so the boys were able to attend private school throughout most of the school year.
As part of a Wal-Mart special sale, it included a DVD featuring a behind-the-scenes glimpse of the Draper-Wolff family and the siblings' bandmates.
The initial band ended, partially due to the conclusion of the television series, which was abruptly cancelled at the request of Draper, who claimed the production schedule was too much for the brothers, on top of their education.
Thereafter, the duo performed at the Earth Day 2010 concert in New York and played many new songs there, such as "Fire and Kerosene", "18", "Disappointed" and others.
[12] After the brothers completed their tour in 2009, they revealed that they were working on a new studio album, post their Nickelodeon TV series.
"[11] Leading up to the album's release, the brothers starred in their own web series on YouTube, which was written and directed by their mother, Polly Draper.
[14] Following a brief period of touring, in October 2013, Nat & Alex Wolff released an album of previously unreleased songs, entitled Throwbacks.
The album primarily consisted of songs the musicians wrote during their time on their Nickelodeon show, The Naked Brothers Band.
Three months later, they released "Last Station/Rules", and, on October 7, an additional double-single, consisting of "Where I'm Goin'" by Alex, and "Rock Star" by Nat, described as 'melodic folk tunes, perfect for a chilly fall day'.
[18] As COVID lockdown forced the brothers to share a living space once again, the two started to collaborate on new music, experimenting with different genres and sounds.
[21] According to Paste Magazine, the Matt Wallace and Tone Def-produced album was 'unrushed, initially meant to come out in 2021, but Alex and Nat chose to push it back while focusing on their ever-more-complex medley of side hustles and big-name gigs.