Comedy is a tough business. What better soil than Chicago could bring an abundance of comic sustenance? We present a portrait of Tom Dreesen. Tom Dreesen was born in a suburb of Chicago in tough times. Rather than planting himself in the somberness of circumstance, he built a comedic style that would yield him a name among the stars. Tom Dreesen may have a quiet tone but don’t get the idea that he isn’t working his talent for a full harvest of laughter. The people we associate with can speak volumes about us. Following that age old adage, we can verify that Tom Dreesen is definitely an entertainer, performer and a singular personality. He has performed with many of the titans of entertainment. Look into his career and you will see names like Frank Sinatra, Sammy Davis Jr., Dean Martin, Tim Reid, David Letterman and Robin Williams gathered around him like a warmed up crowd. If comedy has the power to draw it also has the power of propulsion. It’s a power that drove him from poverty in his early years to stardom and success. With Tim Reid, he formed the first and only biracial comedy duo, Tim and Tom. Tom Dreesen has performed his stand-up comedy in cities across the United States and released a comedy album entitled “That White Boy’s Crazy.” He has made over 500 television appearances including 60 performances on “The Tonight Show” with Johnny Carson. He is a regular guest on his friend David Letterman’s late night talk show and frequently guest hosted “The Late Show with David Letterman” in Dave’s absence. Dreesen has appeared in movies such as “Man on the Moon” and “Spaceballs.” In addition to being a philanthropist, emcee, motivational speaker, Tom Dreesen is first and foremost a stand up comic where for 14 years he opened for the late, great Frank Sinatra. Mr. Tom Dreesen takes us back to his tough beginnings, his challenges and victories. Every moment enriched with the realities of a comedian, an entertainer, a man from the suburbs of Chicago that nourished audiences with laughter.
~ Introduction by Daniel Buckner & Paul Leslie ~
Mark Twain said, “Humor is mankind’s greatest blessing.” Tom Dreesen may concur. It’s a great pleasure.
I’m happy to be here Paul. What’s going on in your life today?
Well, I stayed up all night studying Tom Dreesen and I’ve had two cups of Greek coffee so I am excited to begin this interview.
It would only take about 5 minutes to study Tom Dreesen, but I appreciate you staying up all night to do that.
I think most stories are best from their beginning. If we could go into your house, when you were growing up and we couldn’t see, but we could hear, what would we hear?
You’d hear hungry children saying, “Where can we get something to eat?” I lived in a shack on the Southside of Chicago in Harvey, Illinois. I had 8 brothers and sisters, we were very poor. Five of us actually slept in one bed. We had no bathtub and no shower, and no hot water. It was a rat infested and roach infested shack. And I shined shoes by the time I was 6 years old until I was 12. I set pins in bowling alleys. I caddied in the summer time, I sold newspapers on the corner all to help feed my brothers and sisters so… But I will say all that to tell you that I wasn’t unhappy, I think that is the greatest thing that ever happened to me. So, I am being facetious when I say that you would hear your kids saying, “I’m hungry.” We were poor but again, I had the love for brothers and sisters. At one time, both my parents were alcoholic, but my mom later quit drinking later in life but my dad drink till his death. But again, there was also a lot of laughter. My sisters and my brother and I, we all had some fun and some good times too you know.
Despite all of that, were your parents humorous people?
Not my dad. Here is an interesting twist. First of all, my mother had a great laugh. I loved to make her laugh even when I was a little boy. One time she was very ill and we later found out she had double pneumonia and was taken to the hospital. But where we lived, you never went to doctors. We were so poor and you know, we didn’t go to doctors. The first complete physical I have ever had was at the age of 17 and that was when I enlisted in the Navy you know. So, my mom was later rushed to the hospital because she was so ill. But while she was in bed, I went in and my sisters introduced me as Bing Crosby and I came in with a goofy hat and a pipe and I tried to sing to her. And she just, her laugh, it was just, I thought she had a great laugh and then they introduced me as Bob Hope and I came back out and I did like jokes to her. And so, I can remember her laughter and how much that pleased me to hear the sound of her laughter.
Now, I’m shining shoes in all the bars in my neighbors. There were 36 taverns in Harvey where I grew up, a suburb on the Southside of Chicago like I said and there were 8 taverns in my neighborhood. And that’s where there were all these factories. So, I shined shoes in all these bars and I would go to the bar, well, my mother was a bartender. I would go to her bar that she worked in last and in there was my mother’s brother-in-law, he was my mom’s sister’s husband and he would tell jokes behind the bar. And I was fascinated by him hearing these jokes. I would sit in his bar. I would go to all the bars and I would sit in his bar last waiting for the shifts to change in the factory and I would go back out again with my shoeshine box, but I went there because my mom was a bartender, but also because I loved hearing him telling these jokes so I would sit in the corner and it fascinated me that he could make this sound come out of people’s body by his inflection, by his timing, by his vernacular. It just fascinated me that this sound would come out of their bodies and pull to you like electricity and unite all these people. All these people would all become as one like he would have them laughing all the time. And so I used to emulate him and many tell his jokes and many that shouldn’t be told on a Catholic school playground, but I did it.
How did it feel the first time that you performed on a stage?
I can’t describe to you that feeling. I had wandered endlessly. I came out of the service and I had a job working construction, I wheeled concrete pouring sidewalks and basements. I also worked as a bartender. I worked on the loading dock, loading trucks, I was a teamster and then I later dropped my card and became management for the company, the trucking company. So, I was wandering endlessly. I didn’t really know what it was I wanted to do, but I was frustrated with my life after four years in the service and I joined the Jaycees, a civil group in my community.
And one of the projects I worked on was I wrote a drug education program teaching elementary school children the ills of drug abuse with humor, and those they didn’t teach drug education at a college level or a high school level, let alone an elementary school level. And it was the concept I had to get the kids laughing, playing music and then to plant the seeds. Well, helping me with his project was a young black man named Tim Reid and we worked real well off of one another. We had a great chemistry. And one day a little 8th grade girl said “You guys are funny. You have to become a comedy team.” and the thought of a black and white comedy team intrigued so we started writing what we thought was material.
There were no comedy clubs in those days in America. So, we worked all black clubs in the North and the South and all white clubs as well. When we started out, we were strictly in Chicago you know trying our material out in different places. But I remember the first time on stage with him something that I had written, got a laugh, a big laugh. And it was like an epiphany, it was like an old B-movie, where the dark clouds open up and the sun come bursting through and you hear the angels singing and all that kind of crap. But it really, I went, “Yes! Oh, yes! This is what I want to do.” Inside my being it was like, it is hard to describe that moment, but I knew that that’s what I wanted to do.
And I couldn’t sleep all that night. It was a Friday night and I got up the next morning and I went to church and there’s no service. You know, the Catholic Church that I had been an altar boy, where I sang in the choir when I was little boy and where my mother sing in the choir when she was a little girl. I went to that church it was a Saturday morning and there was no service and I remember, I mean, I knelt down and I prayed and I said, “Yeah, I know what I wanted to do. I finally found what I wanted to do. If you let me make my living as a comedian I will never ask for anything more.” I was doing all these promises, but the thought that you could make a living making people laugh just overwhelmed me and I knew this was what I was going to, I would die trying to do this. My prayers were answered but it took a lot of years. A lot of struggle and everything. But today and for many, many years I’ve been in show business 45 years, I made a living making people laugh.
Now, you mentioned a lot of jobs there that you had. Was there one job that you learned the most from in terms of life lessons and that helped you later?
Well, you know, probably, and that is an interesting question. By the way, no one has ever asked me that question before Paul so… And I’ve done 8 million interviews. That is an interesting question. I would say two things. One was being in the service, obviously that I would engage myself with people that I was in the service with. In the four years I was in the service you take this boy out of the Southside of Chicago and you put him in and there’s a redneck guy from North Carolina, and there’s a black guy from Detroit, there’s an Irish guy from Boston, and an Italian guy from Brooklyn, and all these different—an Asian kid and a Filipino kids, and we are all Americans. But we are from different cultures; and you put us together and we’ve got to keep this ship afloat so to speak. So we have to work together.
No matter what our differences are, no matter what our problems are, we have to work together to make this thing, and through that we bond. So I learned a lot of life lessons from that experience I would say the service was great. But then the other interesting thing would be a bartender, you are being behind a bar in a neighborhood bar, you got to know the people. There were funny people, there were sad people, there were depressed people, there were people who drank to just have some fun, there were people who drank to drown their sorrows. There were people who were accomplishing things in life and there are people who are never going to get any further than where they were. In fact, their dream kind only weren’t going to come true. They weren’t going to ever leave the neighborhood.
So that was really revealing to me. And by the way, I told a lot of jokes behind the bar. Before I ever thought I would be a comedian and you know I kept people laughing all the time and you got more tips that way as well. But I would also create new material, original material about the neighborhood because I knew the characters in the neighborhood. So it was a really a good life’s lesson for me.
Tell me about the comics that influenced you the most.
When I was little boy, we had no television in the shack that I lived in. Everybody else had TVs around the neighborhood and stuff, but the shack I lived in we had no TV so I listened on the radio and of course Bob Hope was a strong influence, hearing Bob Hope on the radio, but there was another show called “Can You Top This?” and it was all these comedians that whatever the subject matter is they would tell a funny story about it. And that really fascinated me, it is early enough. Also, two comedians that influenced me, one was Richard Pryor and the other of course, the other was Jack Benny.
And for two totally different reasons, Richard Pryor spoke from my soul, I grew up in that neighborhood. I grew up in a predominantly black area and I’m a street kid. I don’t have a degree from Macadamia but I got a doctorate from the streets. So watching Richard Pryor and talking about his neighborhood and his material that spoke to my soul. And I met Richard years later and he encouraged me. I did an album in front of an all black audience called “That White Boy is Crazy,” Richard wanted me to call it “That Honky is Crazy” because as you know, he had an album called “That Nigger is Crazy.”
Now, and he said, “Tom, you should do the opposite, ‘That Honky is Crazy’” and I said, “Richard, I would do that, but no black guy ever called me a honky in my whole life.” and I grew up in a predominantly black area. I played basketball in an all black basketball team. I played football on a black football team. I grew up with the brothers and they never called me that, they called me white boy in a very affectionate way. They would say, “Hey, white boy come here. We’re gonna play this afternoon” and they would be arguing about something that is a lie, you know I scored two touchdowns.” They were saying, “Hey, white boy come here, white boy come over here.” and to this day as I go back to my neighborhood those black guys would call me white boy. I was 12 years old when I found out my name wasn’t white boy. So it was an affectionate term.
So Pryor was a great influence on me watching him do his material, but Jack Benny for a totally different reason. I think a person is an artist in any endeavor when they make their work look one word: effortless. Frank Sinatra made singing look easy. “You will be my music, you will be my song” and you will say, “Well, I can do that.” No, you can’t and he just made it look like you could. Jack Benny made comedy look easy and it’s not. He made it look effortless and it’s not, but that’s the way he made it. When I teach young comedians I give classes and I do a seminar sometimes for comedians called “The Joy of Standup Comedy and How to Get There,” where I combine my motivation speeches with teaching young standup comics.
But how do I enjoy this journey? I tell them, if you don’t remember anything I say and I read in the blackboard, “it is conversation and not presentation.” Is it your act? Of course, it is your act, but it is your job to make it look like it is not your act. Like Richard Pryor made it looked like he was standing on a corner, and a bunch of people gathered, and he was coming about things about the neighborhood. Jack Benny made the comedy looked easy and that’s the way it is. You are an artist when you make your work look effortless. But whether you are a truck driver, a bricklayer or a bar tender making your work look effortless.
A moment ago you mentioned Frank Sinatra and you were known for the 14 years you opened for Frank Sinatra. That’s one of things you’re known for. Given his stature as an artist and entertainer, were you nervous to meet him?
I’ll tell you, it’s interesting. First of all, I would like to think that I didn’t open for Frank Sinatra, that he closed for me. But I will leave that to you. I used to tell that joke in front of him and of course, he would get a big kick out of it “That’s right! I close for Tommy.” He had a great sense of humor in that direction you know. First of all let me digress. I was a fan. I mean, when I was little boy, shining shoes in all the bars in my neighborhood he was on the jukebox and where I grew up at people love Frank Sinatra, on the Southside of Chicago, are you kidding me? He had two songs about Chicago. He was the epitome of what live entertainment was all about.
The guys in the bar that were struggling… Frank Sinatra’s daughter once said something very profound Nancy said, “My dad is a winner that losers identify with.” So the guys in my neighborhood whose dreams are never going to come true, whose women left them, with heartaches and sitting in the bar at a quarter to three in the morning, pouring their heart out to the bartender. That’s Frank, “it’s a quarter to three, there is no one in the place, except you and me.” He sang his songs was their life, was the script of their life and I was one of those guy. And here when I first was going to meet him I mean I thought this was going to be the coolest thing in the world and an interesting thing happened.
Many years ago there was a comedian named Pat Henry that opened for Frank Sinatra. And Pat had taken a liking to me. I was performing, opening for Fats Domino in Chicago in a place called Mr. Kelly’s and Pat Henry saw me and he took a liking to me.
He was a veteran comedian and he was opening Frank at that time. So they were in town and he said to me, “Would you like to meet Frank Sinatra?” And I said, “Oh, my god. Yeah! Are you kidding me?” so he took me to the Ambassador East and rank was in the bar in the pump room with his friend and bodyguard Jilly Rizzo and Pat went around the corner and Frank said, “Pat, where the hell have you been?” he said, “I was with my friend. This is my friend Tom Dreesen, a comedian, the kid I told you about.” and Frank looked at me and said, “Hi, kid!” and that’s all he said and I had to leave after that. I went home and I put, “Hi, kid” on my wall and I thought wow, Frank Sinatra said that. But then years later, when I met him I was performing for him. I met him at rehearsal and he was very polite. But by that time I was a veteran comedian I had done a lot of “Tonight Shows,” I had toured with Sammy Davis for 3 years. I toured with Smokey Robinson. I was doing Vegas, Tahoe, Reno, Atlantic City and have done you know, Dinah Shore, Merv Griffin, Mike Douglas and hundreds of shows when I met Frank. So I was a little bit more of a veteran. And yet still was very impressed, but I thought I would work with him one week.
I thought well I was going to work with him one week and then I would try to get my picture taken with him and hang in every bar back in Chicago, but it turned out that on the second night that I was with him, we performed, he and his wife Barbara took me out to dinner. In the middle of dinner I can remember like it was just yesterday, he set his knife and his fork down and he looked at me and he said, “I like your material and I like your style. I’d like you to do a few other dates with me.” and I didn’t say let me check my calendar, I said, “Yeah. Yeah.” and it turned into 14 years and 45, 50 cities a year and a friendship. I was a pallbearer at his funeral and I spoke at his funeral and I miss him every day of my life.
A moment ago, you mentioned, you said Frank Sinatra had a good sense of humor. Could you describe what his sense of humor is like? What kind of stuff really tickled Mr. Sinatra?
Well, by my humble definition Paul a sense of humor is not when you have the ability to laugh at the other shortcomings and misfortunes. It’s when you have the ability to laugh at your own, that’s when you have a good sense of humor and he had one. One night at a bar in Palm Springs, a bar called Chaplin’s Bar, Sydney Chaplin was the owner of the bar. Ironically, he was the son of Charlie Chaplin. He was an old guy and he owned a bar down there. Frank and I used to hang out in it. One night, Sydney would go home at 2 o’clock in the morning and he would lock the place and he would give Frank the keys and say, “You lock up when you leave.” We could stay there and drink.
One night, Frank forgot to lock the front door and I was talking to him looking over and over his shoulder, he didn’t notice, but a car pulled up and this woman got out. There were two women in the car and one of them got out in the driver’s seat in the car and she run in and came in behind Frank. And she said, “Excuse me, excuse me. Do they have a jukebox in here?” and Frank turned around and looked her right in the eye and he said, “I am sorry what did you say?” She said, “Do they have a jukebox in here?” He said, “I don’t think so.” and he is looking around and he said, “No.” and then he looked at her and he said, “I’ll sing for you.” And she said, “No, thanks.” and she turned around and she walked out. And he watched her like a little boy going out the door.
And I said to him, “She obviously didn’t recognize you.” And he said, “Maybe she did.” you know and we both laughed about that. Meaning you could do something on him. You know, they roasted him on “The Dean Martin Roast.” Do you know there are people who can’t be roasted because they don’t have that sense of humor about themselves. But he allowed himself to be roasted a couple of times in his life and so people could poke fun at him. Of course, Don Rickles, their stories are legendary. The Rickles poking fun at him and I could have fun with him, he would laugh at himself, but he also had a weird sense of humor. Sammy Davis, Jr. had a glass eye and Jilly Rizzo has a glass eye, his bodyguard. So Frank, one year at Christmas he bought a set of binoculars saw them in half and sent one to Jilly and one to Sammy Davis.