Updated: August 25, 2009, 5:02 PM ET

Jeff Madsen is feelin' the freestyle

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Wise By Gary Wise
ESPN.com
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Rapping With Jeff Madsen
Jeff Madsen shares his sick flow with the entire poker world.

In 2006, Prahlad Friedman finished 20th in the main event of the World Series of Poker. Seen by many at the time as the top online tournament player in the world, Friedman's superb performance that year should have been remembered for just that. Instead, however, his legacy is mostly composed of these words:

Poker is fun
for ev'ryone
except my opponent,
they shoulda' practiced avoidance.

Friedman, asked by ESPN cameras to deliver a few verses of freestyle rap (as he was known to do on occasion), brought forth that memorable verse and more.

"They put him on the spot and he started messing around and came off pretty bad," remembered pro and aspiring freestyler Jeff Madsen. The result of Friedman's "The Nuts" appearance was mockery of a massive scale, mostly on popular poker message boards where he'd previously been treated like a god. Now, it's Madsen's turn to try his hand, mind and mouth as an amateur freestyle artist performing for millions on national television.

[+] EnlargeJeff Madsen
AP Photo/Jane KalinowskyJeff Madsen has $403,158 in earnings in 2009.

Whether Madsen's performance will be a Friedman repeat or establish the 24-year-old won't be known until it airs on Tuesday night's broadcast (8-10 ET, ESPN) of the 2009 World Series of Poker main event. But what we can bask in now is the realization that he got his chance and took it. Madsen, the former wunderkind who came out of nowhere to win two bracelets and the Player of the Year title in that same 2006 WSOP, is following a dream and having the time of his life doing it.

"I'm excited and maybe a little nervous," admitted Madsen in anticipation of his performance. "I'm going to be rapping in front of the entire world, know what I mean? I was probably more nervous when I did it. Now I can sit back and watch … see how I did."

The question you may be asking yourself is why it matters. You don't see Shaq rapping on NBA broadcasts (though "SportsCenter" may be a different story …), so why will a poker player be doing so during the WSOP? While elements of poker lie in the sports world, others lie closer to entertainment, with exposure and individual branding as important as performance. In a game that's been described as "hours of boredom interspersed with moments of sheer terror," Madsen's turn at the microphone could be described as one of those moments of terror. Reality television at its finest.

"It feels good to be back in the spotlight," said Madsen, whose results, while solid, haven't measured up to the unrealistic projections established in 2006. "I mean, poker's really streaky when it comes to the whole spotlight thing, but it feels good. How important is it to get that attention? I don't think it's that important for me personally, but I know that in poker it helps when it comes to sponsorships and stuff like that. It's good for my career, but I don't care that much about it."

For Madsen, freestyle started out as a hobby but has become a more serious pursuit as his efforts have gained attention in the poker community. "It definitely just started out as fun," said Madsen. "I've been doing it since college. It's still fun, but I think I'm at the point where I do things a little more seriously. Once I get poker figured out and out of the way, I'll try to make some more music."

Once in poker, Madsen's casual rapping was done among friends on a lark. "He'll do it about anything you ask him to," smiled close friend Joy Miller. "We friends used to joke around and say, 'Hey Madsen, why don't you freestyle about this or that,' and he would. It's fun and it's funny. He actually isn't that bad. He's pretty good."

"Jeff has a certain white flavor to his rapping that I appreciate," said PokerRoad owner Joe Sebok, who hosts Madsen blogfessionals that have seen the Californian's previous freestyle efforts. "I'm always more than happy to be in his crew for any subsequent tapings after the ESPN airing. I don't know how seriously he takes it. I think there's a bit of a passion he follows it with. I think he's really into it. At one point he was talking about building a studio in his house."

Is he serious? I'll leave that up to the viewers to decide.

Madsen's mixing of poker and rap started when he informed Sebok of his hobby after Sebok asked him to record those blogfessionals during the 2008 WSOP. "I pushed him into doing it on camera," recalled a laughing Sebok. "We had a lot of fun with it. It was a blast. It just kind of grew from there. ESPN stole it! I made them feel appropriately bad for it. They stole our content! This is just fun. He gets into it. It's a fun thing to do."

"It's all about expressing myself," the artist explains. "I didn't do it to get attention. I'm still pretty shy when it comes to doing it, but I feel good about it. ESPN knew I did this and came to me with the idea to rap for them. I just did it because it's something I like to do. I think I'm good enough to write a song, whether it's poker related or not, I'll keep working at it and I'll definitely put out music at some point. You can criticize if you want. It's all for fun."

While it may be fun, Madsen's foray is the latest example of poker celebrity enabling its players to move into other entertainment forums. Madsen's rapping joins Daniel Negreanu's acting forays and reality TV turns by Annie Duke and Jean-Robert Bellande on a much longer list. Duke's appearance on "The Celebrity Apprentice" made her a recognizable face to millions of viewers outside the poker sphere of influence.

"I think like anything else, you get some exposure and you can broaden your horizons a bit," said Sebok. "I think it's a good thing. Anytime someone can find a creative outlet for the things they want to do, it's always a positive. I'm always excited to see people in poker going after what they want; whether it's going on reality TV or rapping, it's always a positive. It all means more exposure for us. More eyes on the game."

Will Madsen be another Prahlad Friedman? Will this be the opportunity he's been waiting for? Or will he just have the good time he always seems to have and sweep up the viewers in his enthusiasm? Tune in Tuesday night at 8 p.m. ET for the answers.

Gary Wise is a poker columnist for ESPN.com.