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The 40 Most Stylish Moments in "The Simpsons"

9. Krusty Goes Alt Comic

"The Last Temptation of Krust"
Season 9, Episode 15

After being told the material he built his reputation with has gone stale, Krusty adopts the dress, haircut, and cynicism of a late-90's stand up comedian. The T-shirt under a brown blazer, complete with washed denim, an ever-present cigarette, and a constant frown were the uniform du jour for any cynic. Krusty nailed the look, and eventually is able to regain the fame required to sell out to Canyonero.

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