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In It to Win: The Big Business of 'Uncle' Charlie Wilson

Justin Ng/Avalon/ZUMA Press
Charlie Wilson

How the singer’s team keeps him on top after 40 years in the game.

From homeless to headlining the Hollywood Bowl. That's what Charlie Wilson will no doubt be thinking as he steps onstage at the prestigious Los Angeles venue this weekend (Aug. 3-4), backed by the Hollywood Bowl Orchestra.

Wilson's two-night Bowl stand is just the latest salvo in manager Michael Paran's long-term game plan to rebrand the 65-year-old R&B veteran and former Gap Band frontman as a tour and festival headliner. In fact, Paran and Wilson's agent at ICM Partners, partner/head of music Mark Siegel -- in association with AEG -- pulled off another coup in July, when Wilson performed for the first time on the Hyde Park Festival's main stage in London on what Paran calls the festival's "young night," a bill that also featured Bruno MarsKhalid and DNCE.

"Charlie lit the place up so hard that it was like seeing Bruno before Bruno performed," Paran recalls. "We actually lost money doing this show. But it was more important to get Charlie in front of this broader audience of people."

Putting Wilson front and center has been Paran's main strategy since he first met the singer in 1997. Wilson was in his mid-40s at the time, newly sober after a struggle with drugs and homelessness -- at one point literally living in Hollywood alleys for two years -- and still performing local club gigs for $5,000 a night with the Gap Band. Invited by Wilson to manage the band, Paran later assumed the manager role for Wilson himself, his only P Music Group client, when the singer formally launched his solo career in 2000.

"The real challenge was how to make people see Charlie as Charlie Wilson, not the lead singer of the Gap Band," says Paran. "I had to rip that away to move him forward. And that's been the attitude these last 20 years: get him in front of as many people as possible, because after that he sells himself. Charlie just needed someone to believe in him."

Paran found another believer in 2006 after the release of Wilson's image-defining gold album Charlie, Last Name Wilson. That's when ICM's Siegel, whose clients include BabyfaceJ. Cole and Khalid, agreed to represent the 11-time Grammy nominee.

"A lot of buyers don't really understand the R&B world," says Siegel of challenges he and Paran still sometimes face. "That's how I came to describe Charlie as the Bruce Springsteen of R&B. Like Mick Jagger, Charlie sings and dances like he's 35."

Also boosting Wilson's performances is his catalog of solo hits beyond his Gap Band legacy, like "Charlie, Last Name Wilson," "You Are," "There Goes My Baby" and the latest, "I'm Blessed," which led both the Adult R&B Songs and Hot Gospel Songs charts in April. And he's become an elder statesman of sorts to the hip-hop community, contributing to top 20 Hot 100 singles by Kanye West ("Bound 2," "Runaway") and Snoop Dogg ("Beautiful").

"People call him Uncle Charlie for a reason," notes WBLS/WLIB New York operations manager Skip Dillard. "To fans, he's an artist who cares that they paid their money for tickets, got a babysitter, and came out to see him, making them feel that they're getting their money's worth."

Graduating to his first AEG- and P Music Group-produced arena tour in 2015, "Forever Charlie," Wilson grossed $19.4 million over 38 shows, with 18 sellouts, according to Billboard Boxscore. His second AEG/P Music Group arena tour, "In It to Win" in 2017, grossed $15.2 million with 32 shows and 13 sellouts. That showing landed Wilson in third place among the genre's top five R&B touring acts for that year, topped by only Lionel Richie ($19.9 million, 29 shows) and Janet Jackson ($32.9 million, 55 shows). A new tour is anticipated in 2019 after Wilson records his next project.

An Essence Festival mainstay for a decade, Wilson headlined the New Orleans Jazz & Heritage Festival in April and the Hampton Jazz Festival in June. He most recently headlined the Cincinnati Music Festival July 27.

Next on Paran and Siegel's future checklist: Coachella and SXSW, more symphony dates and broadening Wilson's international base. 

"It's an amazing accomplishment to take an artist that no one thought could come back, including his peers, and make him bigger than before," adds Siegel. "Twelve years ago it was Charlie Wilson of the Gap Band. Now it's just Uncle Charlie."

This article originally appeared in the Aug 4 issue of Billboard.