The glorious history of Lil’ Penny

Feb 14, 2015; New York, NY, USA; Team Westbrook legend Penny Hardaway (1) and Team Westbrook forward Tamika Catchings of the Indiana Fever (24, right) high-five during the 2015 NBA All Star Shooting Stars competition at Barclays Center. Mandatory Credit: Bob Donnan-USA TODAY Sports
Feb 14, 2015; New York, NY, USA; Team Westbrook legend Penny Hardaway (1) and Team Westbrook forward Tamika Catchings of the Indiana Fever (24, right) high-five during the 2015 NBA All Star Shooting Stars competition at Barclays Center. Mandatory Credit: Bob Donnan-USA TODAY Sports /
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In the mid-1990s one figure stood above everyone else on the Orlando Magic. And he was a 4-foot tall puppet. Lil’ Penny is one of the iconic ads.

The NBA figured out how to do star endorsements and TV commercials right.

Rather, Nike figured out how to properly market NBA players to a growing consumer base and connect with them in meaningful ways to move product. Michael Jordan‘s marketing revolution in the early 1990s set the tone for modern marketing and how consumers relate to NBA players.

NBA airwaves are flooded with shoe commercials about redemption, expectation and defiance right now. These ads connect emotionally with fans of the sport and tell a part of the story for individual players.

No ad though has had the same lasting power (non-Jordan category) as a series of ads created for the quiet, unassuming, 6-foot-7 point guard for the Orlando Magic.

Anfernee Hardaway was not the typical NBA pitchman. He had all the talent and ability, but a quiet demeanor and unassuming way about him. To sell Hardaway and his signature shoe, he needed a sidekick.

How that ad came together and how it exploded and went viral in marketing circles was recently detailed in an oral history by Adam Caparell of Complex.

It was an ad that had to take selling to happen, some stars to turn them down to get the perfect voice in the up-and-coming Chris Rock and burned bright until the campaign petered out.

In reality, the pairing worked perfectly. Lil’ Penny was the id and ego Hardaway did not have. It added to his story and his personality, selling shoes and becoming one of the most iconic and memorable parts of a memorable and unforgettable Orlando Magic team in the mid-1990s.

"Penny Hardaway, Orlando Magic guard, 1993–1999: I was starting to come into my own in the NBA, and Nike started throwing things at me sneaker-wise and things of that nature. They said, “Since you’re so quiet and reserved and laid-back, wouldn’t it be great to give you an alter ego?” We called the alter ego Lil Penny and I loved it right away, because somebody would be talking trash for me. I thought that was pretty cool.Stacy Wall, former creative director, Wieden+Kennedy: It struck me that the puppet could become his alter ego, but I didn’t want it to suffer the creep factor, so I made sure it was very comedic. He’ll be everything Penny is not in terms of his personality: he’ll be full of ego, he’ll be brash, he’ll be funny, he’ll be unafraid to say Penny is the best."

That is how one of the most memorable and beloved commercial of the 1990s came to be. Nike are just geniuses like that. They took a risk on a somewhat creepy idea and executed it to perfection.

Lil’ Penny was born to be the contrast to Hardaway’s unassuming ways. They enlisted Chris Rock to provide the boisterous voice to contrast with Penny. And the doll became a thing of its own, with its own merchandise and even some thoughts of a TV series or movie. The ads still resonate today.

At its height, Lil’ Penny ads were everywhere, drawing in celebrities like crazy. Lil’ Penny was more of a celebrity than Hardaway in some circles.

As detailed in the 30 for 30, This Magic Moment, the ad wars between Shaquille O’Neal at Reebok and Hardaway at Nike. O’Neal famously had an ad for Reebok where he knocked a puppet looking curiously like Lil’ Penny off a couch. It further stoked the narrative that the Magic’s two stars had some issues behind the scenes.

That can get thrown into the scrap heap of history.

The Lil’ Penny ads were one of the many reasons the 1990s Orlando Magic were so enjoyable. It gave the team some added flare. And it made Penny Hardaway’s career as injuries slowed him down still all the more memorable.

Next: Top 5 international Orlando Magic players

Hardaway’s prime may have been (unfortunately) short lived. But these ads live on forever in the NBA zeitgeist.