"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.