By the time he was a teenager, he was playing on a bill with Presley and Conway Twitty, recording for Phillips and Sun Records, appearing on Arthur Godfrey’s television show and basking in the adulation of a fan club devoted to him. After a stint in the Army, he decided he needed to push beyond country music, and “the only way to do that was to go up north,” he said.
So he headed to Milwaukee and then Chicago, renaming himself Jimmy Damon and by 1968 appearing on “Don McNeill’s Breakfast Club” radio show and regularly at Mister Kelly’s, the Playboy Club, the Empire Room at the Palmer House and other landmark spots.
The 1970s and ’80s were Damon’s heyday, and he hardly could keep up with demands for his art. But by the ’90s most of the old showrooms had disappeared, and Damon had to seek out opportunities in a shrinking environment for his brand of crooning.
“There’s not always a paycheck on Fridays in this business,” Damon told the Tribune in 2011, on the eve of being honored at the annual gala of Chicago Cabaret Professionals, at Park West.
“There have been ups and downs. …
“I only sing for a living – I don’t have (another) job. This is a total commitment.”
You felt that whenever Damon sang. Though he obviously owed an artistic debt to Frank Sinatra, whose music he featured in a Park West tribute in 1995 and elsewhere thereafter, Damon did this music his way. He consistently found his own tempos, dramatic peaks and nuances in Sinatra’s repertoire.
If you weren’t around when Sinatra was king, Damon kept that era alive.
“For those people who were younger and weren’t here for the magic of Mister Kelly’s, the magic of Palmer House, he wanted to let you know: This was fun, these were the great guys,” said music presenter Tracy. “And he wanted to share that with you.”
Even after all those decades, he somehow never lost his ardor for it.
“He always reflected this boyish enthusiasm for the music that was his passion,” said veteran music publicist Debbie Silverman Krolik in an email. “He was a Southern gentleman who made Chicago his home and always was so generous to this city with his musical gift.”
Though Chicago does owe Damon a great deal, the singer felt the debt ran the other way.
“Musically, it’s been a great place for me to learn how to sing,” Damon said in the 2011 Tribune interview.
“What I learned here was how to separate myself from the rest of the acts – how to be Jimmy Damon, not some other creep.”
In addition to his wife, Damon is survived by his daughter, Dana Damon-Trentadue (and her husband Bartolomeo Trentadue); a grandson, Antonio Trentadue; and another daughter, Alexa Damon-Soegaard (and husband Juan Soegaard).
Funeral and memorial services are pending.