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Roger Ebert Finally Wins New Yorker Cartoon Caption Contest After 107 Tries

Film critic Robert Ebert is best known for his Pulitzer Prize-winning and occasionally brutal reviews of movies, but despite his acclaim in the world of criticism, we have learned today that Ebert is still a man much like the rest of us, a man who puts his pants on one leg at a time, a man who just wants to win a cartoon caption contest, dammit.

Ebert has been submitting to The New Yorker caption contest for years now, to no avail; in 2009 he even wrote a blog post lamenting that he had never even been selected as a finalist, despite contributing frequently and often: “I have done more writing for free for the New Yorker in the last five years than for anybody in the previous 40 years.” Now, however, his dream has finally come true as his caption was finally chosen on his 107th try.In 2009, in the same blog post, Ebert expressed his frustration with the judges:

It’s not that I think my cartoon captions are better than anyone else’s, although some weeks, understandably, I do. It’s that just once I want to see one of my damn captions in the magazine that publishes the best cartoons in the world. Is that too much to ask? Maybe I’m too oblique for them. The New Yorker’s judges seem to live inside the box, and too many of their finalists are obvious–even no-brainers, you could say.

Considering his complaints about the conservative approach of the judges, his winning entry (above) was surprisingly off-color, although after seeing some of his other entries we tend to agree that they may not have chosen his very best. The New Yorker has posted several earlier captions and cartoons from Ebert that didn’t make the cut, including a few that seem quite a bit funnier than the ultimate winner. Regardless, hats off to Ebert for his persistence, as well as the news that he has not been deterred by his victory, and has already submitted his entry for attempt #108.

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