107 Tries Later, Ebert Wins New Yorker Caption Contest Film critic had entered it more than 100 times By Evann Gastaldo, Newser Staff Posted Apr 26, 2011 10:42 AM CDT 0 comments Comments In this photo taken Wednesday, Jan. 12, 2011, Pulitzer Prize-winning movie critic Roger Ebert works in his office at the WTTW-TV studios in Chicago. (AP Photo/Charles Rex Arbogast, File) (Newser) – Roger Ebert has entered 107 of the New Yorker's 281 cartoon caption contests, and this week, he finally won. The film critic opined two years ago on his blog that he had "done more writing for free for the New Yorker in the last five years than for anybody in the previous 40 years," and wondered why he had never even been a finalist. To celebrate Ebert's long-awaited triumph, New Yorker cartoon editor Robert Mankoff runs the winning caption as well as some of his favorites of Ebert's past submissions. "Quantity does not guarantee quality," Mankoff writes, but when it comes to cartoon caption contests, quantity certainly helps. "Jack Ziegler, who has published more than fourteen hundred cartoons in the New Yorker, once remarked to me that he finally started getting the hang of it after about the three thousandth one," he concludes. "Well, Roger Ebert certainly has the hang of it now. And I see he has entered contest No. 282, so stay tuned." Click to see the winning caption, check out Ebert's original complaint, or read how you can win the contest.