Clint Black: Newspaper Solicitor

Black, who had a Top Five hit in 1990 with 'Nothing's News,' sold subscriptions for his hometown newspaper, the Houston Post, when he was 14. "One time, a man slammed his door in my face and screamed, 'I don't want no damn paper,'" Black told Reader's Digest. "I forced myself to knock again and was able to tell him how great the paper was. I ended up selling him a subscription."

More From TheBoot