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500 Portraits collects for the first time over two decades of portrait work by the beloved and award-winning creator of Drinky Crow's Maakies, Sock Monkey and Billy Hazelnuts. Tony Millionaire's gorgeous fountain pen illustrations, which mingle naturalistic detail with strong doses of the fanciful and grotesque, include the famous (Bob Dylan), the infamous (Abu Ghraib soldier/model Lynndie England), the fictional (Yoda), the animal kingdom (a cockroach), and everything in between. Literary figures (Hemingway), literary characters (Don Quixote and Sancho Panza), Hollywood legends (Steven Spielberg), comics icons (Hergé) and historical figures (Hitler) also figure prominently.
Millionaire's impeccable linework resembles that of Johnny Gruelle (creator of Raggedy Ann and Andy), whom he cites as one of his main sources of inspiration along with Ernest Shepard and "all those freaks from the '20s and '30s who did the newspaper strips." Many of these 500 portraits were created for The Believer, the magazine founded by Dave Eggers that Millionaire has helped define visually with his signature portraits of interview subjects in every issue since the magazine started. But it also includes dozens if not hundreds of illustrations from various other publications, including The New York Times, The New Yorker, Ephemera Press Historical Maps, The Wall Street Journal, and others.