Column: Catching up with the life and times (and COVID battle) of comic Tom Dreesen, who has written a memoir ‘Still Standing’

Of the comic Tom Dreesen, David Letterman once told me, “I cannot say enough good things about the guy and his comedy. He is one of my oldest friends and a born storyteller. And he’s got such a good heart.”

Those stories and that good heart pepper every page of Dreesen’s new autobiography, “Still Standing … My Journey from Streets and Saloons to the Stage, and Sinatra” (Post Hill Press), written with Darren Grubb and Johnny Russo, with a foreword by Letterman, in which he writes, “Tom Dreesen is not my oldest friend, but he may be my best.”

Dreesen’s life began in once thriving south suburban Harvey. But whatever pleasures were available to most of the suburb’s other children, Dreesen was on the outside. With parents who floated from job to job and in the haze of alcoholism, his life, and those of his seven siblings, was bleak. He writes, “My family seemed to get poorer and poorer. … There was never enough money and we were always way behind in the rent.”

Their “home” was a shack in the shape of a railroad car behind a factory, with no shower, no tub, no hot water. Rats scampered around and sometimes as many as five kids slept in one bed.

From that point, suppose you were to leap forward a couple of hundred pages (and a few decades) in his story? You would understandably be mystified to find Dreesen speaking at the funeral of Frank Sinatra in 1998 and serving as a pall bearer. How could this be?

You’ll learn by reading of his rags-to-Rat Pack journey and it’s an exciting trip.

As a little boy, he shined shoes in Harvey’s many saloons, set pins at its bowling alleys, caddied at Ravisloe Country Club. He enlisted in the Navy, got married, had three kids and settled into a life of working two jobs, playing a little softball, having a few beers.

Prodded by older brother Glenn, he started selling life insurance and joined the Jaycees. That is where he met and started giving talks with Tim Reid, a Black marketing representative from North Carolina. They clicked and were funny and quickly they became the comedy team of Tim and Tom. From 1969 to 1974 they went from small clubs to such hot spots as Mister Kelly’s, the Blue Max and the Playboy Clubs. (Former Chicago sports columnist Ron Rapoport does a deep dive into the comedy duo in his fine 2008 book, “Tim and Tom: An American Comedy in Black and White,” from University of Chicago Press.

Reid left to pursue his dream of becoming an actor, director and producer and he scored quickly, playing the supercool DJ Venus Flytrap on CBS’ “WKRP in Cincinnati.”

Dreesen too went to L.A. and, with his family back in Harvey, slept in his car and headed to the Comedy Store, one of the first comedy clubs, where he begged to get on stage. Older and worldlier than most of the other aspiring comics, he wound up being a pal and mentor to Letterman, Jay Leno, Robin Williams and others.

“Tom was older than the rest of us, had more experience,” Letterman told me some years ago. “Tom taught me, taught a lot of us, what to worry about, what to care about.”

He got his big break when he “killed” on his first “Tonight Show” appearance, and then came more than 500 TV appearances, including 60 more on “The Tonight Show.” He worked as an opening act for, to name just a few, Smokey Robinson, Tony Orlando, Gladys Knight, Liza Minnelli, Sammy Davis Jr. And then came Sinatra.

Each of the stops along this wild road comes with lively anecdotes that display Dreesen’s sincerity and almost childlike enthusiasms. He is, has long been, a rabid fan of the Chicago Cubs, guided by the feeling that, he writes, “Those of us from working-class, blue-collar neighborhoods, we felt a special identification with the plight and pluck of the Cubbies. … (They) represented a summertime version of ourselves. They were doing the same thing, trying their best, but mostly coming up short, hapless.”

His celebrity would eventually allow him to form friendships with some of the team’s stars, such as pitcher Rick Sutcliffe, and work as a bat boy for the team. Naturally, few exulted more when the Cubs won the World Series in 2016: “I experienced emotions that I can’t even describe, but I felt the urge to go visit every grave of every Cubs fan I have ever met in my lifetime.”

He writes about his other sports passion, golf, his three adult children and ex-wife. He is particularly moving when writing about his older sister Darlene, who suffered from multiple sclerosis before it took her life.

Of course, there is also a great deal about Sinatra. It is, in some spots, a feast of name dropping, but one will come to understand why Dreesen remained the singer’s opening act for 14 years, turning down all manner of other opportunities, from starring in sitcoms to hosting game shows. He is aware of the downside of these choices, writing, “My wallet might be fatter had I fully explored one of those career forks in the road.”

He did not because Sinatra was for him, well, Sinatra and all that entailed: “There was a rarefied air surrounding all of it that is hard to describe and impossible to forget.”

He does a pretty good job of describing and you come to know that for him Sinatra became much more. He became the father Dreesen never had. That relationship is vastly more complicated and interesting than what you might be imagining.

The book does address, harrowingly, Dreesen’s battle a few years ago with colon cancer and how that informed his recent tussle with COVID-19.

That is not in this book. It happened earlier this year and so I talked with Dreesen about it.

“With the cancer there were chemo treatments and the realization I could die,” he said from his home. In an unintentional bow to his being a lifelong soft touch for charitable organizations, he lives on Benefit Street in Sherman Oaks, Calif. “It was bad but with COVID I was as sick as I have ever been. The second day in the hospital I really started to think this might be it and I came to the feeling that, ‘Well, if this is it, then this is it.'"

That’s so Dreesen, positive in the extreme. He got out. He feels fine.

There are some people in the entertainment business who find Dreesen too sunny to be true and, in a way, they are right. He is an optimistic man. At the core of his life and humor is genuine sincerity. He doesn’t whine about life’s misfortunes. He does know that his 81 years have been charmed and knows, each day he wakes up, that his has been a wonderful life, slightly surreal but a blast nonetheless.

rkogan@chicagotribune.com

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