Every great entertainer has to start somewhere. That was certainly the case for Kenny Chesney.
On June 10, 1994, a rising Chesney was playing an afternoon set at Houndogs Hot Dogs off Nashville’s Music Row as Fan Fair, which is now CMA Fest, was coming to a close. At the time, Chesney had been in Nashville for three years and his debut album, In My Wildest Dreams, was four weeks old.
Houndogs was run by a man named Buddy Flash, who had hired Chesney in one of his first gigs in town. Flash was a supporter of struggling songwriters looking for their big break, and he would often feed them free hotdogs and lemonade so they wouldn’t go hungry.
Chesney was fired after three days of working at Houndogs. He broke Flash’s No. 1 rule: never leave the eatery’s clowns outside. Chesney was performing at Houndogs that afternoon in 1994 as a thank you to Flash for being there for him when he was new in Nashville.
This weekend’s CMT Hot 20 Countdown will have footage of Chesney’s Houndogs performance. Fans can be seen hanging out at picnic tables, enjoying some dogs and not paying much attention to the star singing for them. An Off Broadway shoe store is now where the hot dog stand used to be.
In 1997, everything changed for Chesney when “She’s Got It All” became his first No. 1 on Billboard’s country singles chart.
“It was a very unsure time of my life,” Chesney tells Hot 20’s Katie Cook. “I didn’t really know where my music was going to take me. I had no idea that my dream would take us to where it took us.”
The CMA’s four-time entertainer of the year headlines two nights at Gillette Stadium in Boston this weekend. He attracted 121,399 fans over two nights when his Spread the Love Tour came to the home of the New England Patriots in 2016. Chesney’s 30-song Live in No Shoes Nation concert album arrives Oct. 27.
An all-new CMT Hot 20 Countdown airs Saturday and Sunday (Aug. 26-27) at 9 a.m. ET.