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Culture | Sep. 2023

DOING IT “HIS WAY”

By Sherry Thomas

ILLUSTRATION BY TOM BACHTELL

74 Tom Dreeson Tom Bachtell Forest And Bluff

Imagine you’re a 10-year-old boy with some shoe polish and a rag going from tavern to tavern in your working class, Chicago area neighborhood of Harvey when all of a sudden, you hear a sound like you’ve never heard before. It’s the 1940s, after the war. Economy’s not exactly booming but people still need shoe shines. The factory near this particular tavern is having a shift change soon so you’re patiently waiting for your mother (a bartender) to get off from work when your uncle (who owns the tavern) starts telling jokes behind the bar. Really good ones. The kind that make people howl so hysterically it’s like they’re having an out of body experience—a joyful, divine, almost otherworldly roar you’ll never forget. “I was in awe,” recalls comedian Tom Dreesen of his childhood (yes, he was that 10-year-old boy). “From that moment forward, I loved hearing jokes and telling jokes.” To say he was obsessed is an understatement. Dreesen got up on stage as soon as he could and never let go of that mic—cultivating a decades-long career that now includes more than 500 appearances on national television, with 61 of those appearances on The Tonight Show with David Letterman (including a few where he hosted the show in Letterman’s absence.) In addition to appearing in multiple movies and sitcoms, Dreesen became a Las Vegas regular, performing with such stars as Sammy Davis Jr., Lisa Minnelli, Smokey Robinson, and Tony Orlando. But none of that compares to what still may be his favorite touring gig of all—opening for none other than Ol’ Blue Eyes himself. “The truth is that during the 14 years that I worked for Frank Sinatra, I turned down more sitcoms than I can even count,” confesses Dreesen, who will bring his one-man show, “The Man Who Made Sinatra Laugh,” to the John & Nancy Hughes Theater at Gorton Center in Lake Forest on September 17. “I was flying on a private jet, staying in his home … it was a great friendship. I knew it was the end of an era and I wanted to be a part of it.” In reflecting on his unlikely path “from Harvey to Hollywood,” he says that in those days, one appearance on The Tonight Show could change your life. “When I did my first appearance on that show, I was broke, and in the unemployment line.” About 24 hours later, the married father of three had a call to be on a sitcom. One of his many early claims to fame was appearing with Tim Reid as America’s first black and white comedy team, and once his career took off, it never stopped—to this day. The 83-year-old performer says he’ll tell some of those stories and others from his autobiography, Still Standing. My Journey from Streets and Saloons to the Stage and Sinatra when he appears in Lake Forest this month. He’s also on the lineup to throw out the first ball at Wrigley Field and sing the 7th inning stretch (ask him about the time he filled in for Harry Carry as announcer). Consider it a sort of homecoming for this Chicago area legend and a celebration of his favorite sound in the world—laughter.

For tickets and more information, visit gortoncenter.org/events/otherevents/.

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