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The 40 Most Stylish Moments in "The Simpsons"

8. Bart and Hugh Hefner

"Krusty Gets Kancelled"
Season 4, Episode 22

When Krusty's ratings begin losing out to the ventriloquiest sensation Gabbo, his show is soon cancelled. All hope is lost for the klown, until Bart and Lisa begin recruiting big-name celebs to star on Krusty's comeback special. While shmoozing with Hugh Hefner, Bart dons an outfit that mimics the playboy's famous cozyboy look. Bart joins the ranks of the nation's best dressed playboys, and finishes the look off with a classy bubble pipe.

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