Drew Friedman is the son of the novelist and scriptwriter Bruce Jay Friedman. Drew, and his brother Josh Allan, grew up in the risqué heart of Manhattan in New York City during the golden age of pornography. Drew Friedman had a monthly cartoon in Spy magazine in the late seventies, and his work has widely appeared, including in MAD Magazine. His brother Josh Friedman wrote columns for Screw Magazine, which were collected as the 'Tales of Times Square' (1993).
Together with his brother Josh Allen, they published 'Any Similarity to Persons Living or Dead is Purely Coincidental (1997), 'Warts and All' (1990) and 'The Private Life of Public Figures' (1993). Drew Friedman won the Newspaper Illustration Award by the National Cartoonist Society for 2000, and recently released his caricatures of 'Old Jewish Comedians' (2006) and the comic art anthology 'The Fun Never Stops' (2007). Among his graphical influences are S. Clay Wilson and Robert Crumb.
His cover for Mad Magazine issue #422 (October 2002) - which caricatured the cast members of the TV show 'The Sopranos' - drew praise from actor Stevie Van Zandt, who played Silvio Dante in the series: "Making the cover of Rolling Stone was nice, but I didn't feel meaningful until I made the cover of Mad Magazine." Actor James Gandolfini (Tony Soprano in the series) was photographed holding the same issue, in the presence of Mad cartoonist Ray Alma. The actual article inside the issue, 'Behind The Scenes of The Sopranos Cast', was written by John Caldwell and drawn by Tom Richmond, but enthusiastically shared by actress Drea De Matteo (Adriana La Cerva) on her Twitter, Instagram and Facebook account on 27 June 2018. Scriptwriter Scott Huver also reflected on this issue, in a 10 January 2019 interview for Variety by Scott Huver: "When we got into Mad Magazine, that was the highlight for me. That said everything. The artist did 'A Mad Magazine Behind the Scenes look at 'The Sopranos'', and it was caricatures of the entire cast and David [Chase]. And I had every actor and David sign it for me, and I’ve got that hanging in my office. Also, MADtv did a great parody early on as well that I thought was great."
A satire of the satirical talk show 'The Daily Show' in issue #467 (July 2006), written by Desmond Devlin and drawn by Drew Friedman, was shown and discussed by Stephen Colbert and Jon Stewart on a 15 June 2006 episode of 'The Daily Show' (Mad's issues often appeared one month early on the market).
He wrote a personal homage to Robert Crumb in Monte Beauchamp's book 'The Life and Times of R. Crumb. Comments From Contemporaries (St. Martin's Griffin, New York, 1998), of which he also illustrated the book cover.
