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15 Greatest Footwear Commercials of All Time

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#8 Nike Air Max Penny 1: Lil’ Penny 1996

Voiced by legendary actor/comedian Chris Rock, Lil’ Penny was quite possibly the funniest character in footwear history. As Anfernee Hardaway’s alter ego Lil’ Penny was loud, in your face and had jokes for days –an extrovert- and the opposite of the self described introvert that was Hardaway. While all of the Lil’ Penny appearances were entertaining, it was this 1996 commercial that showcased Hardaway in a cheesy 70’s themed commercial for the Air Max Penny 1 while Lil Penny and Hardaway watched on TV together that stood out among them all. It was the only commercial where both Hardaway and Lil Penny were equally funny and because of this landed this commercial at the 8th spot.