He still accepts that it is a struggle to reinvent his music without losing fans.
"It's always difficult to be careful. A lot of people try hard and they miss and they fall. I know how far I can go with my older fans," Wilson said. "After I did There Goes My Baby, I didn't think I could top that record. I didn't want to do another record."
For him, this was a very heartfelt song, as his first time singing it was for his friend Snoop Dogg, and his wife Shante, renewing their wedding vows. The record stayed on the Billboard Urban Adult Contemporary chart for ten weeks.
Still, Uncle Charlie has to work hard to sell his records, but not just because of the illegal downloading. He also has to battle radio stations. "Some of these stations don't want Charlie, they say you don't fit the demographic," said Wilson.
He admits that he has to be careful what he says on his tracks, and some things he chooses to leave out.
"I ain't telling anybody about my bedroom; that is none of your business!" said Wilson.
He may have to watch some of his content now at his age, but Wilson still reminisces about his humble beginnings with his brothers.
"I miss the earlier Gap Band days, just me and my brothers. I miss them so much," said Wilson. He was planning a reunion show with his younger brother, Robert, no less than a year ago,but by the time returned from a series of concert dates to find that his brother had passed away.
Wilson called the death of Robert, at the age of 53, from a heart attack, a "bombshell". The silver lining is that Wilson refuses to stop bringing his soul enriching music to his fans. He has even broken out and done collaborations with artists such as Kanye West, Justin Timberlake, and Beyonce.
"It's a lot of people that would love to sing with Charlie Wilson. It's a lot of artists with whom I'd love to work," said Wilson.
Fortunately for D.C., Charlie Wilson will be hitting the Constitution Hall alongside Jennifer Hudson, Miguel, and En Vogue on Saturday, July 23, 2011, which will prove to be a show stopping concert.
"I love all my D.C. fans you have always been there for me. I have overcome too many obstacles, and if you want to look at me as a testament, then go ahead", said Wilson.
He is talking about his alcohol and drug addiction he suffered.
For Wilson, it has been a happy continuing, when it comes to his career. Make sure you get a ticket to see him, that is, If you think you can handle his electrifying performance.