Comics and Stamps Have a Longer History than You’d Expect
The U.S. Postal Service has just issued another set of comics-related stamps. Stamp collecting is an old hobby, and one that's perhaps faded somewhat, but comics and stamps have a longer history than you'd expect. The 'Sunday Funnies' series includes Beetle Bailey, Calvin and Hobbes, Archie, Garfield, and Dennis the Menace. Archie's best known for the comic books, of course, but Allen Holtz's excellent reference program (and now a blog) Stripper's Guide says it started appearing in Sunday newspapers in 1946.
So when did the first cartoonist or comic appear on a U.S. stamp?
6. All of the above
If you selected all of the above, one can make a reasonable argument that you're correct. The first cartoonist to design a stamp was noted editorial cartoonist Jay "Ding" Darling in 1934—however, he drew "Mallards" for the U.S. Department of Agriculture Migratory Bird Hunting permit stamp. A Duck Stamp is sold annually to hunters and is used to fund National Wildlife sites.
In 1956, a children's stamp "Friendship—the Key to World Peace" was designed by high school senior Ron Dias, who later became a Disney animator. 1966 saw a "Bill of Rights 175th Anniversary" stamp by Washington Post political cartoonist Herbert "Herblock" Block. Walt Disney was honored in 1968; this first Disney stamp eventually led to a stunning amount of them worldwide. In 1993, Bill Mauldin's Willie & Joe became the first comic strip characters to appear on stamps, as part of a sheet commemorating World War II; Mauldin got a stamp of his own earlier this year.
Other cartoon stamps of note were 1988's "Australia Bicentennial" by editorial cartoonist Pat Oliphant, a cartoon of a koala and bald eagle that was a joint issue with Australia; 1989's "National Association of Letter Carriers centennial" by Jack Davis, the great caricaturist and Mad Magazine artist; 1991's "Comedians" series by caricaturist Al Hirschfeld, who also did 1994's "Silent Screen Stars"; and the New Yorker's James Thurber also got a self-portrait caricature stamp in 1994.
In 1995, the situation changed to include recognizable cartoon characters, when the "Comic Strip Classics" sheets recognized the accepted centennial of the comic strip, largely due to lobbying by Mort Walker. These included The Yellow Kid by R.F.Outcault, The Katzenjammer Kids by Rudolph Dirks, Little Nemo in Slumberland by Winsor McCay, Bringing Up Father by George McManus, Krazy Kat by George Herriman, Rube Goldberg Inventions by Rube Goldberg, Toonerville Folks by Fontaine Fox, Gasoline Alley by Frank King, Barney Google by Billy DeBeck, Little Orphan Annie by Harold Gray, Popeye by E.C. Segar, Blondie by Chic Young, Dick Tracy by Chester Gould, Alley Oop by V.T.Hamlin, Nancy by Ernie Bushmiller, Flash Gordon by Alex Raymond, Li'l Abner by Al Capp, Terry and the Pirates by Milton Caniff, Prince Valiant by Harold R. Foster, and Brenda Starr by Dale Messick. About two-thirds of these strips were still in production, and with the rules changed about depicting licensed or trademarked characters, the floodgates opened (relatively). From 1997 to 2001, an annual Looney Tunes stamp came out including Bugs Bunny, Sylvester and Tweety, Daffy Duck, Wile E. Coyote, and Road Runner and ending with Porky Pig. These were followed by a Disney animation series from 2004-2008, "The Art of Disney: Friendship, Romance, Magic and Imagination." A series on "Classic American Dolls" had three cartoonists' creations included—Johnny Gruelle's Raggedy Ann, Percy Crosby's Skippy, and Rose O'Neill's Scootles. O'Neill was the cartoonist who created Kewpie dolls. 1998-1999's "Celebrate the Century" series had comics scattered throughout it including the Gibson Girl by Charles Dana Gibson, a "Teddy" bear created by cartoonist Clifford Berryman in 1902, a flapper based on John Held Jr.'s work, the first comic book character on a stamp with "Superman Arrives," another Disney stamp of "Walt Disney's Snow White Debuts" and the Beatles' Yellow Submarine animated film. Of special interest was a set of 10 DC Comics stamp albums that had superheroes explaining historical events. Charles Schulz's death in 2001 led to a Peanuts stamp with Snoopy shown on his doghouse. DC Comics characters appeared in 2006 and Marvel Comics ones in 2007, while 2009 saw a set of five Simpsons stamps. Finally, illustrator Drew Struzan regularly paints popular culture stamps, and has also done Star Wars and other comic book covers.
The situation in other countries is different. European nations put out regular series of cartoon stamps and their post offices appear at comic conventions. France, Belgium, and the Netherlands are particularly productive. American cartoonists can be featured on these stamps—Don Rosa's Donald Duck art appeared in 2001 on Finnish stamps. In Asia, Japan has been doing a regular manga or anime stamp for more than 10 years. Latin American countries put their local characters on stamps too, but Caribbean and African countries frequently issue "stamps" just to raise revenue—the stamps feature characters like Betty Boop and are sold in the U.S., but aren't really used for postage in their own countries. In the past few years, Zazzle has been selling postage—cartoonists can do stamps of their own characters, like Bill Griffith has done with Zippy, or major companies like Disney can sell hundreds of different stamps of their characters. I attempt to keep up on some of the cartoon stamp news at my Cartoonphilately blog and invite anyone who's read this far to check it out.