For six nights only, Mike Tyson will leave his mark, for better or worse, on the Great White Way. The former prizefighter has paired up with director Spike Lee to bring his one-man show The Undisputed Truth to Broadway, a highly anticipated debut for both. It’s a promising pairing bound to entertain audiences, but at what cost?

Tyson is the heavyweight champion of career turn arounds. A mere five years ago, the boxer was wallowing at the presumable rock-bottom of his career, struggling with drug addiction, bankruptcy and a dead end career. He was bound to be a memory, with a small chance of a few denigrating reality TV show appearances.

And yet surprisingly his career has skyrocketed to success once again, this time capitalizing on his former personality and exploits via appearances of TV, stage and film. Mike Tyson: The Undisputed Truth is the only live version of this new career path, a one-man show that weaves together stories of Tyson’s life in his signature, candid and raw way. Tyson described his performance, which debuted in Vegas earlier this year, as “naked,” and “very vulnerable” to the New York Times, and critics have held a similar opinion.

“Some of it can still make you shift uncomfortably in your seat, like when Tyson talks about being with Japanese prostitutes before his upset loss to Buster Douglas in Tokyo,” the Associated Press wrote. “Somehow, though, it works — in a lot of ways.”

It worked enough to convince Spike Lee to use it for his Broadway directing debut, pairing the boxer with a Hollywood talent who’d bring a great deal of press to his tale of hard knocks. Lee calls Tyson’s life “a great American story,” and audiences can expect that same self-depreciating humor that has become Tyson’s trademark in the past few years.

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The catch with self-depreciating humor is that you can never exactly tell which joke the audience is enjoying: are they laughing with you, or at you? The goofy-guy thing he has going works in large part because for the longest time, that’s what he was not: not someone to laugh with, let alone make the butt of a joke. Arguably America’s scariest pro-boxer, Tyson is now America’s most laughable teddy bear, who refers to himself as a “wimp.”

Some will enjoy Tyson’s play just off the sheer audacity of his life. However others may take the opportunity to laugh at him, the fallen boxer with the funny lisp and sagging physical frame. Try as he may to reconcile his past with his present, there’s still so much of Tyson that’s hard to understand and relate to, and adding humor into that confusion can be very polarizing from a viewer’s perspective.

Tyson is either incredibly career savvy, or desperate for money. Or a little bit of both. The reality is Tyson’s got considerable debt, and high-profile gigs help him keep collectors at bay. Whether or not audiences are in on his joke may be of no concern to he who has bills to pay.