Bad-Boy Pitchmen

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Shoe marketers trying to reach trendsetting young urban males have discovered a fact long known by any weary eighth-grade teacher: guys love a troublemaker. Celebrity endorsers typically have been squeaky-clean family men like Cal Ripken Jr. or harmless rebels like long-haired Andre Agassi. But today's sneaker ads often showcase figures known as much for alleged misdeeds as for their accomplishments. When a company attaches its brand to these antiheroes, "it's a way of saying, 'We're in touch with somebody who is street real,'" says Rick Burton, professor of sports marketing at the University of Oregon. And it's a way of accomplishing that enduring goal of youth--upsetting Mom. --By Rebecca Winters

ALLEN IVERSON The Philadelphia 76ers guard was charged with multiple felonies after he allegedly went on a gun-wielding rampage in pursuit of his wife. Yet his Reebok goods continued their steady rise in sales. Most charges were later dropped against the 2000-2001 MVP, here in an ad with his son

ROBERT DOWNEY JR. The Academy Award-nominated actor has been arrested for cocaine and heroin possession. His ads for Skechers shoes started running in magazines like Rolling Stone in April

PETE ROSE On billboards and bus benches, Pony is campaigning for the rehabilitation of the former Cincinnati Red, who was barred from baseball amid accusations that he gambled on games. In this ad Rose reminds fans of his 4,256 hits, still a major league record

JACK (THE ASSASSIN) TATUM Another Pony poster boy, the former Oakland Raider was known for his crushing hits while on the team in the 1970s, including one that paralyzed a player in an exhibition game