Tom Dreesen: From Rough Road to Streets of Dreams

-by Mark Casasanto, images courtesy of Tom Dreesen

October, 1948. Tom Dreesen was nine years old when Harvey, Illinois celebrated the success of its native son, baseball star, Lou Boudreau. The American League MVP was a player / manager of the Cleveland Indians whom had just won the World Series.

People were lining the streets and following in their cars, honking horns as they processed to the local high school field. Dreesen, wanting to be part of the excitement, hurriedly walked the long route to the ceremony. Despite the exhausting effort, he arrived after all was said and done, save for a local television personality, signing the last few autographs for some remaining children. He didn’t know who she was, his family didn’t own a TV. He asked for an autograph anyway. On a discarded ice cream wrapper, and with a borrowed pencil, he got her signature. 

As young Tommy Dreesen worked his way back home, he couldn’t help but wonder, what it would be like to be recognized in such a way…


Weekly paychecks routinely got pissed away in neighborhood bars, unpaid rent and missed meals became the stark reality. As the middle child in a seemingly ever growing family, Dreesen did what he could to help make ends meet. Shagging errant golf balls for a few cents each, shining shoes, pin setting at the local bowling alley and selling newspapers during lunchtime of the school day was the norm. There wasn’t anything he wouldn’t do for love of family. “Any blue collar family… you always knew, you had to work for it if you were gonna get, it… it was the mantra in my neighborhood” he says with no regrets.

He spent the majority of his time on the streets. Oddly, it made for a certain freedom and there, he felt some semblance of control. Along with his older brother Glenn, who served as his de facto protector and way finder, Tom would sometime spend hours trying to find a means to provide a fuel source for their apartment’s old coal stove. That often meant stealing coal from the train yard, one brick at a time while high atop a train hopper. “There was no such thing as welfare in those days” he says. “It was meant to be… later on in life, I was prepared to overcome adversity.”

Before long, he started to run with a rough crowd, a gang, ironically called… The Jokers. By sixteen he had dropped out of high school and like his brother before him, he would soon find himself in Navy whites.


The Navy was a life changing experience for Dreesen. The showers, meals and clothing that were all but unattainable to him as a youth were suddenly stabilizing normals. But, he also experienced the ugly scowl of racism first hand. While ashore in Norfolk, as they were being asked to leave a bar because of a shipmate’s skin color, a bouncer decided he didn’t want to entertain any attempt at reasoning from Dreesen. Blindsided, he was cracked upside his head with a leather rapped slap jack. Chronic tinnitus is a ringing reminder of that incident. 

After an honorable discharge, and navigating a revolving door of occupations, opportunity knocked in a rather unique way. “There was something gnawing at me all the time… I wasn’t doing what I was put on this planet to do” he reflects. Being a spiritual man, he started to pray… a lot.

Having joined the civic minded Jaycees a couple years earlier, Dreesen sought support for a program he had written on drug abuse and intended for children attending integrated schools. The concept was simple: get the kids to buy in to the message through laughs, music and establishing a credible connection. Although Dreesen initially committed to working with another presenter, fate stepped in, when his planned partner… stepped out.

Tim Reid was essentially the new kid in town. Like Dreesen, he was eager to get involved in his community and made himself available to help. “Talk about prayers being answered” Dreesen regaled. “When we walked into that classroom, we got their attention immediately!”

Tim and Tom

And so, at the suggestion of an 8th grade girl who told them that they were really funny, Tim and Tom pursued a standup act. It wasn’t exactly easy sailing for America’s first, and only, black and white comedy team in 1969. Still, the pair went anywhere there was racial tension and never shied away from the uncomfortableness. Because of their partnership, he says, “White people hated me… black people hated Tim.” It was classic divide and conquer. Tim Reid and Tom Dreesen however, refused to let it to happen. 


By 1974, after some years of moderate success, Tim had decided to give a solo career a shot. The groundbreaking duo would soon take their final bows leaving Dreesen to again ponder his future. One night in a bar, he made a decision to quit drinking and headed west after the last scheduled performance of Tim and Tom.

Bouncing around Los Angeles, he stayed in borrowed rooms, abandoned vehicles and cleaned up in gas station restrooms while hitch hiking to and from The Comedy Store. All in search of that one big break. Despite telling his wife he’d be back in a week, some thirty days after landing at LAX, he finally got the audition he so desperately sought.

Amongst the regulars at the club that Dreesen now called his performing home, a virtual who’s who of American Comedy- Robin Williams, Jay Leno, Elayne Boosler and a shy, fellow midwesterner who remains one of his best friends, David Letterman. 

He started to persistently pester Craig Tennis, the Talent Coordinator for The Tonight Show. Tennis, who was the ticket to Johnny Carson’s show, finally acquiesced and sat in on the comedian’s set. Less than a week later, he was booked. In classic Carson fashion however, Dreesen was bumped three consecutive times before finally getting the “go” on his fourth attempt.

“Standing behind that curtain… all those dues… all those hardships… it was all for that one moment in time,” he affirms. One by one, he began appearing on all the major talk and variety shows while steadily logging sixty-one Tonight Show appearances. His life had changed forever.

Dreesen with Johnny Carson


Good fortune, once so elusive, started to shine down on Dreesen. After long seeking a slot on the Sammy and Company Show, his agent got a call early one morning. The ask was big… could Dreesen possibly make it to Lake Tahoe for a taping later that day? A comedic replacement act was needed to cover an unexpected cancellation. To Burbank he went… up, up and away! He landed in Reno and eventually made the ninety minute drive to Tahoe.

After a brief tete’-a-tete’ with the producer who was concerned about his material, Dreesen held fast and steady. He performed his set, about a white guy playing on an all black basketball team, as planned. “The routine killed,” he says amusingly. “Sammy fell off the couch laughing.” Afterward, Sammy Davis, Jr. said to him, “you’re coming with me!”.

Accepting that invitation to appear, on such short notice, would pay dividends for years to come. Throughout 1977, he played one sold out show after another, opening for the best all around entertainer of the era. “Sammy never forgot where he came from and what he did for me in Las Vegas when we got to Caesar’s Palace was monumental,” he says with emphasis. 

The showroom at Caesars was a notoriously hard room to work for comedians. Aside from the clinking and clanking of waitstaff clearing dinner plates before the headliner began, the room had high ceilings. Laughter notoriously got lost in its cavernous dimensions. Aware that it was Dreesen’s first gig in Vegas and a potential make or break performance for him, Sammy Davis, Jr. decided to open the show himself that evening. He knocked out a few numbers before yielding to the comic. And high above Las Vegas Boulevard, Dreesen also had marquee billing. Sammy basically set the table so that Dreesen could continue to eat.

In a stroke of true comedic genius but with all humility intended, Dreesen hit the stage that night and simply said: “I never dreamed that the great Sammy Davis, Jr. would be my opening act.”

Dreesen was garnering a lot of attention within the industry. A bona fide touring act, he was on the road with Smokey Robinson in Lake Tahoe. After his set, he ran over to the neighboring Harrah’s Hotel where Frank and Nancy Sinatra were appearing. As he made his way to the showroom, he happened upon the vice president of Harrah’s Reno and Lake Tahoe, Holmes Hendrickson. That chance meeting turned into maybe the most important introduction of his life. Frank Sinatra’s manager, Mickey Rudin, took an instant liking to Dreesen that night. A few days later, he was asked to open for Sinatra at the Golden Nugget in Atlantic City. Together, they never looked back.


“Make no mistake about it,” Dressen declares. “Frank Sinatra was the boss.” And in the beginning, that’s exactly how Dreesen played it. “I never let him know just how in awe of him I actually was… he didn’t need another fan, I picked up on that immediately.” In part, it’s one of the reasons their relationship grew beyond headliner and opener. When the tuxedoes came off, they were genuine buddies… Staying up all night while on the road or at the compound in Palm Springs. Sometimes, just the two of them, riding around the desert until the morning bright. Laughing. Talking. Listening. 

At the core, they were just two neighborhood guys, who grew up around saloons and shared many of the same inherent values. From the smallest of traits like being precisely punctual and irritably impatient to larger beliefs in faith, charity and their Italian heritage. 

In the latter stages of Sinatra’s career, their relationship became more father and son like. “Ya know, everybody needs a go to guy, someone you can go to and bare your soul.” Dreesen truly believes, he was that guy, a guardian if you will, for a then, more vulnerable Frank Sinatra. 

Towards the end, one night, as he was readying to leave the compound, they had a rather poignant exchange. In essence, it was really uneasy attempts at goodbyes. Dreesen sensed it. He tried to light a fire within his pal, encouraging him to get well so they could hit the road again. Frank Sinatra simply responded, “you’re going to have to go on the road by yourself from now on Tommy”.

Dreesen with Frank Sinatra


Through it all, Tom Dreesen, as the title of his recent book suggests, is indeed, Still Standing. Frankly, it’s a fascinating read about a remarkable American success story. Like Howard Cosell once said of Francis Albert Sinatra, “the great man… who knows what losing means… as so many have…”, Dreesen continues to march forward, starring in his own main event. 

He’s beat cancer twice, recently whipped Covid and still continues to make people smile while constantly giving of himself. And as for his understated golf game? “Sometimes I play like Ben Hogan, sometimes more like Hulk Hogan,” he deadpans.

For perspective, Dreesen closes his eyes and views his journey through the eyes of his ten year old self. Trudging through the snow, saloon to saloon, shining shoes, listening to Ol’ Blue Eyes on the jukebox. For fourteen years, he was part of his inner circle. And every night, after exiting stage right, Frank Sinatra would call him back on for bows and proclaim, “there he is, that’s my man, my main man… Tommy Dreesen ladies and gentlemen.”

Dreesen’s book, Still Standing… is available on and 

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