This weekend I’ve been bumping Akon’s Konvicted, which is set to drop on Tuesday. It’s going to be interesting to see how it performs. When Akon debuted with Trouble back in June of 2004, nobody really knew who he was. His first week sales were abysmal, coming in somewhere near the 5K mark. But over the course of a year he blew up, went platinum and became the new Nate Dogg. I’ve always been curious how that happened.

Obviously Akon is a major talent. And I can see why he would appeal to a broad range of people. He’s street enough for the thugs. His bad boy, no-shirt crooning is likely to intrigue the TRL crowd. The Africa connection (he grew up in Senegal) endears him to audiences overseas. Still, what exactly is it that causes a relative no-name to hit so huge?

I interviewed Akon a couple weeks ago for Pound Magazine and asked him that very question. The R&B singer explained that he made a concerted effort to market himself differently than other new artists. Instead of doing club tours and performing to apathetic crowds that would rather get their drink on, he did prison shows. The prison population is a captive audience, desperate for anything that changes up their routine. What’s more, since Akon has done his own bids, his music deals with subjects most inmates can relate to. Playing for the incarcerated generated buzz behind bars, which translated to buzz on the streets. Once he had the streets, the industry and radio followed.

But this explanation only goes so far. Akon did the legwork, sure, but what was the spark that allowed his grassroots campaign to catch fire? Whenever an album is transformed from a simple product to a cultural moment, there has to be a bigger story.

In this case, I think Akon gives voice to a particular experience—one that doesn’t get spoken about often. His persona reminds me of Somali-Canadian rapper K’naan’s song “Struggling." There’s a few lines of the track that have always stood out to me: “Mostly, I’m up stressing when other folks sleep/Believe me, I know struggle and struggle knows me/My life owes me/Like an overdose, I’m slowly/Drifting into the arms of trouble/Then trouble holds me/And nothing else is close to me/More than pain, unfortunately/Like a self-fulfilling prophecy I’m supposed to be/Struggling.”

Anyone who has ever watched someone they love drift into the arms of trouble is going to understand what I’m getting at here. (And with the criminal justice system perpetually widening its net and becoming its own industry, more and more people will have this experience in the future.) Both the media and mainstream culture as a whole tend to demonize those that get caught up in crime. But, in reality, most guys that end up in jail aren’t bad people at all.

Akon speaks to these men, and to anyone who has ever cared about them. He comes from a world of men who grew up with nothing. Men who got tired of straining to pay bills and being treated like shit at low-paying jobs. Men who couldn’t take it anymore, and decided, fuck it, let me make some money. Men who did things in the night that paid for crisp white sneakers and shiny black Benzes. For a little bit of pride, for a little bit of recognition.

Akon is that guy you grew up with who meant well but messed up. He’s the guy that got caught up and then locked up. He’s the guy that has a big heart, that’s loyal to a fault, that always reps for family and friends. The guy that made some bad choices and now has to pay the price. And that price, when it isn’t death, is extreme loneliness.

The funny thing about Akon is that he doesn’t even have to sing about all of this to evoke it. His voice is drenched in this particular brand of melancholy, regret and longing. His tone and pitch are inseparable from his back story.

So, even though Akon’s sophomore joint branches out in content—with songs about sex (“Smack That” and “I Wanna Love You”), love (“Don’t Matter”), his homeland (“Mama Africa”)—and even though it’s not quite as good as his debut, I expect his fans will stick by him. Once somebody has told your story, you don’t tend to forget them.