Rare “Little Orphan Annie” artwork offered at auction this week

The original art from the oldest “Little Orphan Annie” comic strip ever brought to market, published in the first month of the strip’s appearance 94 years ago, will make pop culture history this Friday, 22nd February, in Heritage Auctions’ Comics & Comic Art Auction in Dallas.

The item rubs shoulders with a host of art by British artists featured in the upcoming auction, as previously reported – including Dave Gibbons cover for Watchmen #1 and a number of covers created for early Marvel UK comics by American artists.

Creator Harold Gray’s “Little Orphan Annie” strip art is dated “8-26-24” and debuted in the New York Daily News and the Chicago Tribune through the Tribune-News Syndicate.

Only a small portion of “Little Orphan Annie” comic strip original art is available on the collecting market, because almost all existing originals reside in the permanent collection at Boston University, making this an exceedingly appealing opportunity for serious collectors.

“Harold Gray’s ‘Little Orphan Annie’ quickly became an American classic as it embodied the true spirit of the American experience,” Heritage Auctions Comic Art Specialist Weldon Adams said.

“This plucky orphan girl, adopted by a benevolent Captain of Industry, would go on to become a big star in radio, books, movies, and possibly most importantly, in marketable licensed product! A true bit of Americana in print form.”

Carrying a pre-auction estimate of $5,000-up, this is just the 19th daily in the series and also features the seldom-seen Mrs. Warbucks; her appearances were rare, and she ultimately was written out of the series, which still runs in some newspapers today. The character has had an extraordinary run of popularity, evolving from the comic strip into a slew of projects including appearances on radio, as a Broadway musical and in feature films, as well as a collection of licensed products.

In this example, Gray, who wrote and drew endless adventures and misfortunes for 11-year-old Annie strip for 44 years until 1967, includes large drawings of Annie in each panel. Titled “The Bubble-Buster,” it is drawn in ink over graphite on Bristol board, and is signed by Gray in the last panel.

Also in the auction is a “Little Orphan Annie” strip dated 10-6-25, published in the Chicago Tribune in 1925. Annie’s strip was just over a year old when this was published but by this point, Harold Gray had already developed Annie into the form we most know… The art is also signed by Gray in the last panel, and also personalized and signed at the bottom of the last panel.

Other US newspaper strip artworks in the auction include a 1932 episode of “Krazy Kat” by George Herriman, a 1936 Mickey Mouse” strip by Floyd Gottfredson and “Terry and the Pirates” strips by Milton Caniff, including a 1936 episode, from the second year of the feature. This daily stars the evil Dragon Lady, and she has the most horrible torture in mind for her captive… shaving off his mustache and washing out his hair product!

Heritage Auctions is the largest fine art and collectibles auction house founded in the United States, and the world’s largest collectibles auctioneer. Heritage maintains offices in New York, Dallas, Beverly Hills, San Francisco, Chicago, Palm Beach, London, Paris, Geneva, Amsterdam and Hong Kong.

Check out the full catalogue for the upcoming Heritage Auctions’ Comics & Comic Art Auction in Dallas here

The Harold Gray collection at Boston University consists of artwork, printed material, correspondence, manuscripts, photographs, and other items

Artwork in the collection primarily consists of Gray’s original pen and ink drawings for “Little Orphan Annie”. The daily strips date from 1924 to 1968, and the Sunday strips date from 1924 to 1964. Also included are Gray’s original drawings for “Maw Green” (1933-1964) and “Private Life Of…” (1931), as well as original drawings and watercolors for various Christmas cards and other miscellaneous ink sketches. An original drawings for a strip of “Brenda Starr” by Dale Messick is also included

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John Freeman

The founder of downthetubes, John works as a comics editor, writer, as Creative Consultant on the Dan Dare audio adventures for B7 Media, and on promotional work for the Lakes International Comic Art Festival. Working in British comics publishing for over 30 years, his credits include editor of titles such as Doctor Who Magazine, Star Trek Magazine and Babylon 5 Magazine. He also edited the comics anthology STRIP Magazine and edited several audio comics for ROK Comics. He has also edited several comic collections, including volumes of “Charley’s War and “Dan Dare”. He’s the writer of “Crucible”, a creator-owned project with 2000AD artist Smuzz, published on Tapastic; and “Death Duty” and “Skow Dogs” with Dave Hailwood for digital comic 100% Biodegradable.

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