Millionaire was born in Boston and grew up in and around the seaside town of Gloucester, Massachusetts. He came from a family of artists – his father was a commercial illustrator, his mother and grandparents were painters – and was encouraged to draw from an early age. His grandfather, who was a friend of the cartoonist Roy Crane, had a large collection of old Sunday comics which were an early source of inspiration to Millionaire. He drew his first comic strip, “about an egg-shaped superhero who flew around talking about how great he was and then crashing into a cliff,” when he was nine years old. At age 13 he lost his natural front teeth in a car accident; since then he has worn false teeth. During high school Millionaire continued to draw comic strips for his own amusement.
After high school Millionaire attended the Massachusetts College of Art, where he majored in painting, but left without graduating after getting three quarters through his fourth year. While in college he began drawing houses in wealthy neighborhoods for money; this, along with occasional illustration jobs, would be his primary source of income for the next 20 years. After college he moved from place to place, living in Boston, Florida, California, and Italy before settling in Berlin for five years during the 1980s. Returning to the U.S. in the early ’90s, he moved to Brooklyn, where he began drawing a regular comic strip, Medea’s Weekend, for the Williamsburg newsweekly Waterfront Week.
One night at a local bar, the Six Twelve, Millionaire drew “a cartoon about a little bird who drank booze and blew his brains out” on a napkin – the origin of his best-known character, Drinky Crow. The bartender encouraged him to draw more cartoons, offering him a free beer for each one he completed. After doing many of these cocktail napkin drawings, Millionaire began drawing more polished versions of his cartoons for publication in various zines, including Ninny, Spike Vrusho’s Murtaugh and Selwyn Harris’s HappyLand. He also did drawings for several trade journals and Al Goldstein’s notorious tabloid Screw. Eventually the alternative newsweekly New York Press asked him to draw a weekly strip, and in 1994 Maakies debuted in its pages. It soon spread to other papers across the country. During the mid-2000s, Millionaire transferred Maakies to The Village Voice as its NYC venue, but returned it to the Press in February 2007.
Besides Maakies, Millionaire has produced a series of comics and picture books collectively titled Sock Monkey. He has also occasionally contributed to comics anthologies including Legal Action Comics, Star Wars Tales, Dirty Stories, and Bizarro Comics. His illustrations are published in many leading venues including The New York Times, The New Yorker and The Wall Street Journal. Currently he does much of the artwork, along with Charles Burns, for Dave Eggers’ magazine The Believer. Animated versions of his work have been featured on Saturday Night Live, in the They Might Be Giants documentary Gigantic (A Tale of Two Johns), and on Adult Swim. In 2006 Fantagraphics Books published his graphic novel Billy Hazelnuts. He is working on a children’s book to be published by Hyperion. Since February 10, 2010, Millionaire’s comic Maakies, has been published weekly in Nib-Lit Comics journal.
Millionaire moved to Los Angeles in 1998. He currently lives in Pasadena with his wife Becky Thyre and two daughters Phoebe and Pearl.
He is the brother-in-law of the artist and poet Jon Sarkin and television talk show co-host, Andy Richter.