Looking back, it might have been one of the most successful media makeovers of the twenty-first century. In the fall of 2007, Mark Cuban—the Internet billionaire turned Dallas Mavericks owner, known for his courtside temper tantrums and the hefty fines they engendered—turned up as a competitor on the fifth season of the ABC reality series Dancing With the Stars. Usually seen in public wearing oversized T-shirts and a openmouthed look of indignation, Cuban this time donned tight-fitting dance pants, sleeveless shirts that showed off his muscles, and a grin that stretched from ear to ear. Nobody expected him to get very far, up against more famous celebrities (Marie Osmond, Wayne Newton) and more naturally gifted physical performers (singer Sabrina Bryan, former Spice Girl Mel B). But Cuban bounded across the stage, a clumsy yet eager student of the cha-cha, mambo, and jive, his tongue lolling around in his mouth, like a puppy racing through the fields. Having just recovered from hip replacement surgery (in the first episode, viewers were shown the large scar on his buttocks), he emerged as endearingly human and fragile, the underdog you wanted to root for.
By the time he got voted off, during week five, regular Dancing With the Stars viewers could only marvel. For someone with a reputation as a megalomaniac and a brat, Mark Cuban was pretty darn charming. (No doubt Tom DeLay thought he might pull off a similar trick when he appeared on the same show two years later. Lightning did not strike twice.)
The unlikely rehabilitation continues: Last summer, Cuban turned up as himself for a three-episode arc on HBO’s Entourage, where Jerry Ferrara’s Turtle tried to get him to invest in a tequila company. His performance was funny, relaxed, and slyly self-aware; he played up his reputation as a bit of a dick while also letting the audience know that he was in on the joke. This spring, he appeared as a guest “shark” on two episodes of ABC’s reality program Shark Tank, in which self-made American business icons like Barbara Corcoran and Kevin Harrington listen to the pitches of would-be entrepreneurs and negotiate investment deals with them. Jumping enthusiastically into the fray—within the first fifteen minutes of the season premiere, he double-crossed fellow shark Robert Herjavec to buy into an Internet toy business—Cuban once again appeared to be having a grand time. ( ABC would do well to make him a fixture on this terrifically watchable show.) With his ill-conceived 2004 reality series, The Benefactor, now mostly forgotten and with Donald Trump, his chief competitor in the billionaire-on-reality- TV sweepstakes, busy considering a presidential run, only one question remains: Why hasn’t Mark Cuban yet made the leap from supporting banana to full-blown star?
To make sense of Cuban’s place in the pop culture firmament, of course, you need a quick history lesson: It wasn’t always that American businessmen felt the compulsion to take to the airwaves and build a cult of personality. In 1984 Lee Iacocca published his autobiography, a genial if self-aggrandizing assessment of how he turned Chrysler around and made himself rich. A guest spot on Miami Vice notwithstanding, Iacocca didn’t quite have a taste for the tawdrier glare of the public spotlight. But then came Trump. An alternately comical and creepy embodiment of the eighties “greed is good” ethos, he lived out his life in the New York Post’s Page Six gossip column, all the while turning out self-aggrandizing nonfiction best-sellers of his own. In 2004 his reality show, The Apprentice, in which contestants compete for a job with Trump, became the ultimate symbol for a generation that viewed making money as the most glamorous of pursuits.
Cuban’s misfortune—insofar as a billionaire’s inability to have his own top-rated TV series can be labeled a misfortune—is that he entered this strange fame-seeking game a little too late, when the notion of the corporate-titan-as-paparazzi-magnet was no longer a novelty. (He made his billions in 1999, when he sold his Internet start-up Broadcast.com to Yahoo.) He also stumbled badly in transparently aping Trump with The Benefactor, which followed The Apprentice to air by just eight months. The concept of the series was vague, with contestants engaging in seemingly random stunts in the hopes that Cuban would give them $1 million. The star, meanwhile, came off smug and capricious and eccentric, as if Howard Hughes had been reincarnated as a frat boy. ( The Benefactor was canceled after just six episodes.) Indeed, seven years later, even after the successes of Dancing With the Stars and Shark Tank, it’s still difficult