After high school, Millionaire attended the
Massachusetts College of Art, where he majored in painting. While in college, he began drawing houses for money; this, along with occasional illustration jobs, would be his primary source of income for the next 20 years. After graduating from 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 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
New York Press in February 2007. Besides
Maakies, Millionaire produced a series of comics and picture books, collectively titled
Sock Monkey. He formerly contributed to
comics anthologies including
Legal Action Comics,
Star Wars Tales, Marvel's
Strange Tales,
Dirty Stories, and DC's
Bizarro Comics. His illustrations were published in publications including
The New York Times,
The New Yorker and
The Wall Street Journal. For a time he contributed art to
Dave Eggers' magazine
The Believer. Animated versions of his work were featured on
Saturday Night Live, in the
They Might Be Giants documentary
Gigantic, and on
Adult Swim. In 2006,
Fantagraphics Books published his
graphic novel Billy Hazelnuts. He did the cover art for
Elvis Costello's 2009 album
Secret, Profane & Sugarcane. Starting February 10, 2010, Millionaire's comic
Maakies was published weekly in
Nib-Lit for a period of time. Nib-Lit went offline by 2020 leaving Millionaire without an outlet for his work. ==Style and influences==