In 1983, while he was opening for Smokey Robinson, Mr. Dreesen met Sinatra’s lawyer, Mickey Rudin, and impressed him with his glibness. Soon after, Mr. Dreesen got an offer to open for Sinatra in Atlantic City, N.J.
“I thought, ‘Wow, this is great. I’ll work with him for a week, and I’ll get a picture taken with him, which I can hang inside every tavern in Harvey and that’ll be that,’” he recalled in “Still Standing … My Journey From Streets and Saloons to the Stage, and Sinatra” (2020), written with Darren Grubb and Johnny Russo.
That week turned into 13 years with Sinatra, performing in 45 to 50 cities annually. “This was truly the life I wanted,” he wrote, reflecting on idolizing Sinatra since he was a boy. “From my vantage point, every night, there was no TV series, no radio show, no movie deal that compared to what I was experiencing.”
After Sinatra’s death in 1998, Mr. Dreesen was a pallbearer and the M.C. at his funeral.
Sinatra is one of many subjects that Mr. Dreesen discusses in a podcast — “Who’s Tom Dreesen?” — that he started earlier this year with Joe Goal, a friend and actor. “He wanted to get his life out there,” Mr. Goal said in an interview.
Mr. Dreesen was also renowned for his philanthropic work, often as the host of fund-raising events for charities, including those supported by pro-am golf tournaments; he was an ardent golfer.
In 1997, Jim Murray, the Pulitzer Prize-winning sports columnist of The Los Angeles Times, wrote that Mr. Dreesen was as “necessary to the well-being of the game’s essential pro-ams as the ropes, the marshals, the scorekeepers, the army of other volunteers.”
