At the height of his tennis career in the 1980s — when his game was as explosive as his temper and he had a total disregard for country club politesse — John McEnroe was just the Superbrat talent to captivate the Me Generation. His seven Grand Slam singles titles (three at Wimbledon; four at the U.S. Open) are remembered as much as his racquet-smashing antics and foul-mouthed disputes with officials — bad behavior he's since parlayed into shtick, from American Express and All-Bran commercials to the catchphrase title of his 2002 memoir, You Cannot Be Serious. "McEnroe was more of the tortured artist," tennis writer Joel Drucker muses.

"Why can someone create such beautiful music with his racket and such noise with his mouth?" But it was McEnroe's left-handiwork — deft volleys and power shots — that made his indelible mark on the court. "His game was a form of death by paper cut," Drucker says. "He was very smart at working the court and angles and spins and variety."

Teetering between existential crisis and indulged privilege, the Holden Caulfield of tennis captured the marketing imagination of Nike co-founder Phil Knight, who discovered him in mid-tantrum on the 1978 Wimbledon practice courts. The resulting "Rebel With a Cause" campaign proved prophetic for company and player. "If you look at the shoe McEnroe- was wearing then, it's pretty much just full-grain leather, so when it wore out, it was down to his sock," says Jeff Perkins, current footwear product director for Nike. "Now we are engineering the rubber compounds for durability, airbags for cushioning, shank devices for increased rigidity, the platform of the shoe as low to the ground as possible." Thus the Air Zoom Mo GT Court model shown here.

During a trip to Nike's Portland headquarters in 1983, where an innovation group was sharing the latest training sneakers, the precocious McEnroe grabbed a racquetball shoe prototype with added ankle support from the bottom of a paper bag. "The guys were freaking out because this wasn't supposed to go to market," Perkins recalls. "It was an advanced concept, and suddenly he started wearing this shoe and immediately playing his tournament matches in it." McEnroe was never one for formality — he once made a stir in the player's tearoom at Wimbledon by eating the traditional strawberries and cream without a spoon. As they say, if the shoe fits.