[7] He was expelled from high school for giving a speech exposing "salacious dirty laundry" about the teachers, and within a year had moved to Toronto to take a sitcom writing class.
[7] Grove Press released Nesteroff's first book, The Comedians: Drunks, Thieves, Scoundrels and the History of American Comedy[8] on November 3, 2015, to positive reviews.
"[14] Nesteroff's second book, We Had A Little Real Estate Problem: The Unheralded Story of Native Americans and Comedy,[15] was released on February 16, 2021 by Simon & Schuster.
[23] Major Indigenous authors including Stephen Graham Jones, David Treuer, and Philip J. Deloria[21] have also lauded the project.
[24] Colby Cosh wrote in his National Post synopsis, "I decided that I wasn’t sure whether the material was promising, but also that Nesteroff couldn't write a bad book if you kicked him in the head and cut off his thumbs.
Other television appearances include the Judd Apatow documentary George Carlin's American Dream on HBO, W. Kamau Bell's We Need to Talk About Cosby on Showtime, Kevin Hart's Right to Offend on A&E, and The Dark Side of Comedy on Vice TV.
[60] The Hollywood Reporter announced in May 2016 that Nesteroff was curating the National Comedy Center, which houses George Carlin's personal archive.
[62] One critic described his Toronto engagement as "heroin for comedy nerds ... Nesteroff shared dozens of unforgettable stand-up-related tales from the early 19th century to now.
The depth of his knowledge about the history of American comedy combined with his off-the-cuff and funny yet eloquent stage presence made this entire show utterly engrossing.
[80][81] He has appeared on the programs of Adam Carolla,[82] Illeana Douglas,[83] Dana Gould,[84][85] Greg Fitzsimmons,[86] Moshe Kasher,[87] Slate.com,[88] Longform,[89] Tom Scharpling,[90][91] and Doug Stanhope.
"[95] Nesteroff was included on LA Weekly's Best of Los Angeles list in 2016,[96] and was dubbed the "premier popular historian of comedy" by the New York Times in 2021.