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.