This Artist Sent Thousands Of Dumb Drawings To Celebrities And Got Them Autographed (48 Pics)

There's collecting celebrity autographs, and then there's spending more than a decade mailing deliberately ridiculous drawings to famous people in the hope that they'll sign them. Artist and writer Alex Leeds chose the second approach, turning what might sound like a completely absurd idea into a project involving thousands of drawings, countless envelopes, and some surprisingly cooperative celebrities.

The results of this unusual experiment have now been collected in “Dumb Drawings Autographed By Celebrities,” a humor book released by Library Tales Publishing on October 20, 2026. The concept is simple: Leeds creates intentionally silly illustrations, sends them to celebrities, and waits to see whether they'll autograph them and mail them back. Over the years, he's spent more than $5,000 on postage alone, proving that even the most ridiculous artistic endeavors can require some serious dedication. What makes the project particularly entertaining is the connection, or sometimes complete lack thereof, between the drawings and the people signing them.

Below, we've gathered a selection of Leeds' amusing creations to give you a closer look at his unusual artistic experiment. Scroll down to explore the drawings, and don't forget to let us know in the comments which celebrity and illustration pairing you found the funniest!

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