Andy Friedman and MAD's Mort Drucker, 2012

Photo: Arnie Levin

Andy received his first professional illustration assignment in 1990 at the age of fifteen, while he was still a sophomore in high school.  The commission came from The Metropolitan Life Insurance Company, for whom he drew cartoon portraits of thirty employees to be presented at an awards banquet honoring Joan Rivers, who also received a portrait (along with her dog, Spike).  His career as an editorial caricaturist was officially launched in 1999 when he accepted an assignment to draw Hank Williams III for The New Yorker.

Hank Williams III for The New Yorker, 1999

The Dalai Llama for Reader's Digest, 2015

Isaac Asimov for MIT Technology Review, 2015

Chubby Checker for Philadelphia Magazine, 2015

Icons of Romantic Comedy for, 2014

(Clockwise from top L) Gustave Flaubert, David Foster Wallace, Virginia Woolf,

Zora Neale Hurston, and Daniel Defoe for The Atlantic, 2014

Former Phillies manager Charlie Manuel for Philadelphia Magazine, 2014

Sleeping beneath the blue whale at the Museum of Natural History in NYC for New York, 2014

"The Cocktail Party of 1969" for Esquire, 2013

Louis CK for Playboy, 2013

Tupac Shakur for The New Yorker, 2013

Senator Mitch McConnell for The New Yorker, 2013

Roseanne Barr for Rolling Stone, 2013

"Harbinger" cover, 2013

"It's Always Sunny in Philadelphia" for The New Yorker, 2013

Wallace Shawn for The New Yorker, 2013

Drake for Rolling Stone, 2013

"Sex and the City" meets "The Sopranos" for The New Yorker, 2013

President Barack Obama for The New Yorker, 2012

L to R: Jeffrey Katzenberg, Sherry Lansing, Michael Eisner, Eddie Murphy, Goldie Hawn, Michael Ovitz, and Sylvester Stallone dining at Morton's for The Hollywood Reporter, 2012

Bruno Mars for Rolling Stone, 2012

From Dana Milbank's "Don't Miss Guide To The 2012 Republican and Democratic National Conventions"

for The Washington Post, 2012

NJ Governor Chris Christie attempts to align with Bruce Springsteen for The Atlantic, 2012

The annual meeting of the World Economic Forum in Davos, Switzerland, for The New Yorker, 2012

Cover for New Selected Essays: Where I Live, by Tennesee Williams (New Directions), 2009

Presidents watch their first ladies perform for Japan's Asahi Shimbun Globe, 2009

L to R: Mark Twain, Stephen Colbert, Al Franken, and Jon Stewart for The Atlantic, 2009

Levon Helm for The New Yorker, 2008

Leonard Cohen for The New Yorker, 2008

Chief Justices Clarence Thomas and Ruth Bader-Ginsburg with a generic CEO for The New York Times Magazine, 2008

Bob Dylan for The New Yorker, 2006

To view an archive of all of Andy Friedman's published illustrations, please visit