Akon’s blend of R&B and hip-hop with his African roots has made the former jailbird a global superstar.

Akon is pacing the stage at the Air Canada Centre in Toronto, crooning the buttery-smooth chorus to his hit song "Don't Matter". The mournful ballad is reminiscent of '60s soul, yet Akon's rich, nasal voice is unmistakably African and his swagger is all raw, uncut hip-hop. The contrast is both startling and strikingly cosmopolitan.

Just as he has lulled the audience into a trance, he changes tempo and launches into the frisky club anthem "Smack That"–and thousands of female fans follow suit, twisting in their seats like strippers, screaming for the R&B singer to get nasty. Grinning, Akon obliges, peeling off his white tank top to reveal a chiselled physique. But he switches gears again and belts out the haunting hook for "I Tried", a collaboration with Bone Thugs-N-Harmony that's currently topping the charts. The melancholy meditation on street life recalls Akon's past, infusing the mood with a note of hopelessness so familiar to the hip-hop generation.

It's a complicated dance that Akon is performing–this collage of cultural sensibilities and sounds–but he's pulling it off. In the space of just three years, the Senegalese-American artist has transformed himself from a convict into a global superstar, managing to satisfy the streets and the mall, the city and the slums, North America and the developing world, black and white. He'll showcase that dance here when he appears with Gwen Stefani and Lady Sovereign on Friday (June 15) at GM Place.

Akon's journey has spanned 34 years and two continents. Although he was born in St. Louis, Missouri, the son of African jazz percussionist Mor Thiam and dancer Kiné Thiam, Aliaune Thiam grew up in Senegal. At the age of seven, his family moved to New Jersey. In spite of a comfortable middle-class upbringing, Akon was drawn to the streets and ultimately got caught up in armed robbery and a car-theft ring, trading music-industry dreams for a jail sentence. It was there that he conceived his debut record, Trouble , which was picked up by Steve Rifkind at SRC Records and released in 2004.

The album started out slowly, but its powerful single "Locked Up" triggered grassroots support that eventually pushed it past the platinum mark. When Akon released his sophomore album, Konvicted , in late 2006, it exploded, shooting his total sales to 5.2 million albums worldwide.

"I knew it wasn't going to do big numbers the first week," Akon said of Trouble when he called the Straight . "We had to figure out another way to promote this album without doing the basic–going to clubs and performing. I think that's real boring. People don't pay attention.

"The majority of this record was written in jail, so I felt we should do a penitentiary tour," he continued. "All those people would be able to understand this record. Plus, it's the best way to get to the streets." Akon got permits and began visiting prisons, including the notorious Rikers Island jail complex in New York City. Inmates started telling friends and family on the outside to call radio stations and request his songs.

"Everybody loved the record," the singer-rapper recalled. "It just snowballed. Before you know it, I'm doing a whole bunch of juvenile facilities. We covered a lot of ground. Once Connecticut picked up, the whole East Coast just followed. Next thing you know, the South picked up, West Coast picked up, and then internationally–just like wildfire."

The prison visits represented a shrewd business strategy, but they also proved powerful on a personal level. "It was the greatest feeling ever, knowing that I'm going into a jail and I can walk right out again," Akon remembered. "I knew for a fact that I was a whole other person now, and I never wanted to go back ever again."

That determination to move forward is being tested by the pressures of fame. Like many other celebrities, Akon appears to be grappling with his own self-destructive demons. Just as he has achieved pop-music dominance–working with A-list artists ranging from Young Jeezy to Gwen Stefani–he's messed up. In Trinidad in April, the singer engaged in a provocative on-stage dance with a teenage fan who turned out to be the daughter of a local preacher. Public outrage cost Akon corporate sponsorship from Verizon Wireless, which dropped him from its music ads and scuttled its Gwen Stefani tour sponsorship. Then on June 3, he acted out again at a concert in Fishkill, New York, tossing a teenage boy from the stage.

Such missteps, though, will likely only further endear Akon to his hard-core hip-hop fan base, which relates to the cinematic narrative that he has so artfully constructed: that of a troubled underdog, perpetually struggling but managing to win–and to win big.