October 13, 2006, was a key date for the online poker community.

It was the day that Congress passed the Unlawful Internet Gambling Enforcement Act, a last-minute addendum to the Port Security bill. It banned payment processors in the US from doing business with online poker sites and was an opening shot in the battle that eventually led to the Black Friday closedown of much of the industry. 

Whilst the effects of that decision were felt across the industry for many years, there was an immediate impact on the televised poker industry at the time. Televised poker is popular in 2021, but in 2006 it was hit by the UIGEA and saw the demise of what might have gone on to become the most important hybrid show in history – Hip Hop Hold’em.

“The original idea was to have the music stars come on and play poker and banter at the table,” said Tone Boots, executive producer and showrunner of Hip Hop Hold’em. “And then, at the end of the show, they’d do a musical performance. We had 11 episodes shot and nine edited when the [UIGEA] was passed. That’s what killed the show.”

A few live performances were filmed, with Ludacris featuring in an early show. He was about to drop Release Therapy and already had a string of number ones to his name. He was a huge coup for a new show and would have helped drive the concept within the hip hop community, although as Boots admits, getting ten stars per episode could have been a challenge.

“I had to have ten celebrity hip hop artists show up in one day,” Boots added in the June 2021 interview. “Which in and of itself is an impossible task. Fortunately, we were shooting in Manhattan because the rule of thumb is that if you add a bridge or a tunnel between a rap star and a location, you’re begging them to be at least an hour or two late.”

However, once a couple of early episodes aired, the show gained popularity and began to snowball. It seemed Boots and his backers had hit upon an idea that was set to take the poker world by storm. Even stars who you wouldn’t think had a basic grasp of poker hand rankings, such as Mary J Blige, wanted to get on board, which meant Boots had to teach them how to play the game before they came on.

“Believe it or not, a lot of black people don’t play poker. Therefore, a lot of hip hop artists weren’t familiar with poker, and that was a hurdle for us. They knew how to play stuff like spades and other card games, but they had no clue how to play poker whatsoever.”

However, once they understood the basics, those stars were soon on board.

“Once they saw it air and how it looked we got people like Q-Tip, Mary J. Blige and P. Diddy all wanting to come on the show.” All were huge stars, even back then, and added to the credibility of the show. Sadly, the UIGEA decision killed off the fledgling show before it could really take off, but it remains something of a cult classic, despite airing for just a single season.

Since 2007, the relationship between poker and hip hop has grown, with music videos featuring the imagery, some songs drawing on poker themes and artists even indulging themselves. With such strong connections, one can only imagine how popular Hip Hop Hold’em might have been were it not for that cruel twist of fate in 2006.

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