Michael Jordan was easily the most popular basketball personality of the 1990s. But riding the G.O.A.T.’s coattails just might be a plastic puppet standing less than two feet tall and wearing fire kicks.

Debuting in 1995, Lil Penny—the Chris Rock-voiced puppet alter ego of superstar Anfernee “Penny” Hardaway—took the NBA and pop culture by storm. The Nike commercials starring Penny and his miniature sidekick were huge hits and helped push sneakers, of course, but also a book and other merchandise, appearances on Oprah, and nearly a movie. The ad campaign, which lasted two years, became one of Nike’s most successful and undoubtedly amongst its most memorable.

But Lil Penny—the beloved trash-talking player who threw the best parties, hung hard with the NBA’s top talent, and could never stop sweating Tyra Banks—was almost left on the cutting-room floor.

It all started in 1994, when Jordan was still months away from making his triumphant (and first) return to the NBA and Nike was looking to create new buzz around Hardaway, the third pick in the 1993 draft, who was starting to establish himself as one of the game’s rising stars. Stacy Wall, then creative director for renowned advertising agency Wieden+Kennedy, was tasked with the job, and he drew inspiration from a failed commercial concept featuring Hardaway and Jordan playing one-on-one as puppets for his new pitch.               

“I thought the commercial was interesting, but Nike thought it was creepy,” recalls Wall, currently partner and director of Imperial Woodpecker, a commercial production company. “But the Penny puppet in particular had this sort of magic to it. I was frustrated as a creative that that campaign was not going to happen and that the puppet itself had ended up on the shelf at Nike.”

It didn’t stay there for long. Wall refined the idea and, looking to the tag-team dynamic of the Spike Lee-Jordan commercials of the late ‘80s, pitched Nike a different idea: the modest and reserved Hardaway would have a trash-talking sidekick puppet. Nike loved it and gave Wall the green light.

Many years and many commercials later (it’s been nearly two decades since the last ad aired), Lil Penny still cracks up people who grew up in the '90s watching the spots on TV; even those who never saw Hardaway play have discovered him and his sidekick on YouTube. So how did it all come together? Why was it so successful? And how would the campaign have been different if Nike landed its first choice for the voice of Lil Penny? Drawing from exclusive interviews from Wall, Charles Barkley, Kenny Smith, Tyra Banks, Penny Hardaway himself, and others, we present the oral history of Lil Penny.

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