An Examined Life with Jeff Allen 46: The Tonight Show, The Improv & the Early Days of Chicago Comedy with Tom Dreesen

An Examined Life with Jeff Allen 46: The Tonight Show, The Improv & the Early Days of Chicago Comedy with Tom Dreesen February 9, 2016


Tom Dreesen is the main reason I became a stand up comedian. We both grew up in the south suburbs of Chicago, and while I am still struggling to sell my wares, Tom is known in Chicago as the “Godfather of Comedy”. He has made over 500 appearances on national television as a stand-up comedian, including more that 60 appearances on The Tonight Show. He was a favorite guest of David Letterman, and frequently hosted the show in Letterman’s absence. For 13 years he toured cross country and opened for Frank Sinatra, and has appeared countless times in Las Vegas, Tahoe, Reno and Atlantic City with artists like Smokey Robinson, Liza Minnelli, Natalie Cole and Sammy Davis, Jr. Tom has acted in numerous television shows and appeared in motion pictures including one of my all-time favorites, Spaceballs with Mel Brooks. He has recorded comedy albums, starred in his own TV comedy special, Dreesen Street, and hosted a late night talk show in Chicago, and so much more.Tom Dreesen

I recently heard him holding court for a whole bunch of us at the Laugh Factory, and all I kept thinking was, “I wish I would have heard Tom’s wisdom 35 years ago. It would have made such a huge difference in my career and my life!” He offers motivational speeches for universities and corporations, but one of the things he enjoys most these days is speaking to fellow stand up comedians, spotlighting the joy that exists in doing what we do. As Tom puts it, being a stand up comic is one of the greatest professions on the planet. We get to travel all over and make people laugh. And because people laugh, they are healthier for it. So, we not only entertain, but we improve people’s physical, emotional and psychological health while doing it! Or, as Tom puts it, we are “physicians of the soul”.

Despite this, there is so much negativity in our business. Tom alone knows five amazing comedians who recently committed suicide. With this in mind, Tom strives to encourage his fellow comics and teach them how to take on life’s ups, downs, successes and rejections.

I remember hearing Tom at the Comedy Cottage back in the late 70’s, when I had just started, hammering home the point that no single comic can do all the work that’s out there. There’ enough work out there for all of us, so if you ARE working, reach back and help the guy who’s behind you. The reality is that our business can be pretty cutthroat, unless we each follow Tom’s advice… and luckily, there are more than a few of us who do.

Image: Univ. of Chicago Books
Image: Univ. of Chicago Books

But, Tom has always been one to buck trends, dating back to his early years when he performed with Tim Reid as the Tim and Tom Show. Tom wrote about those days in his book, Tim and Tom: An American Comedy in Black and White. Tom’s stories are as historical as they are hysterical, and I think it’s a must read! It seems that most people in America today have forgotten what race relations were really like in the 60’s, so to hear perspectives from the first African American/Caucasian comedy team should be mandatory for young people today.

At the time, Tom was wandering around aimlessly after serving in the Navy, going from one job to another, never finding contentment in anything, but also not knowing what he wanted to do. It was during this time in his life when he penned a drug education program, which taught grade-schoolers the dangers of drug use, using humor as his main vehicle. Tom had noticed that there wasn’t any drug abuse education taking place in our colleges or high schools, but there needed to be… even at the grade school age, in order to establish a knowledge of the ills of drug use in our kids at an early age. Joining Tom in this project was a young, very funny, black man named Tim Reid. From the very first classroom they went to speak to, Tom knew they had something special. They were sent into integrated classrooms, which were rare in that part of the country in those days. Students back then weren’t used to seeing a young black man and young white man working together, especially telling jokes while delivering important life lessons. In no time, the program spread to all 50 states and 22 foreign countries.

One day, a little girl approached them after their anti-drug program and told them, “You guys are so funny, you should become a comedy team!” Now, there were no comedy clubs in those days, so as they wrote their material together, they honed their act performing in little jazz clubs here and there. Before they knew it, Tim and Tom were a bona fide act and performed together for over six years, and their story is now in development to become a movie!

Now, keep in mind, people never saw a black guy and a white guy walking down the street together in those days, much less performing side-by-side doing comedy together. So, as they initially worked in all-black clubs, they ran across one guy in particular who hated white people. Yet, when they met, he wasn’t mad at Tom, he was mad at Tim for being with this white guy! And they ran into like-minded people at the all-white clubs as well… guys who hated Tom for being a N_____-Lover and working with a black man. Yet, despite encountering all this racism and the violence that came with it, Tim and Tom persevered, made thousands of people laugh, and they are still friends today!

In the early 70’s the team split up so that Tim could pursue his acting career, and he may be best known from his work in WKRP in Cincinnati, Simon & Simon, Sister, Sister and That ‘70’s Show. Meanwhile, Tom was pounding the pavement in L.A., trying to figure out a way to get onto the Tonight Show with Johnny Carson.   In fact, Tom had to wait a month before he even got a chance to do five minutes in front of Mitzi Shore, the owner of L.A.’s The Comedy Store, just to get her approval and be allowed to stand on her hallowed stage. But, once he made Mitzi laugh, he was allowed to perform all the time with fellow “unknown comics” like Robin Williams, David Letterman, Jay Leno, Gallagher, Michael Keaton, and the girl waiting tables there was Debra Winger, who would eventually move from waitress to Academy Award Nominated Leading Lady!

In those days, stand up comedy became equivalent to rock and roll, in regards to entertainment esteem. The talent coordinators for The Tonight Show, Merv Griffin, Mike Douglas, Dinah Shore, Hollywood Squares, as well as American Bandstand and Soul Train would scour the local clubs, looking for the “next great stand up comedian”. Needless to say, the energy buzz backstage at The Comedy Store was incredible back then with guys getting bookings of a lifetime each and every weekend.

After a year of pestering, Tom finally convinced the booker for The Tonight Show to come see him and a new kid at the time named Billy Crystal. That night, Tom got invited to come to the talent scout’s office the next day, where he told Tom, “I saw what you can do in 20 minutes, show me – right now – what you would do if I gave you five minutes on the Tonight Show stage.” And just like that, Tom was booked for the following Tuesday on the greatest late night show and comedy launch pad ever!

That following Tuesday, Tom arrived early. He patiently waited in wardrobe. He got dolled up in hair and make up. He then waited for his introduction in the green room. When all of a sudden, a producer came in and told him that they had run out of time and he got bumped. Ever the optimist, Tom didn’t lose faith and was re-booked for the following week. Just like the week before, Tom arrived early, he went to wardrobe, hair and make up, and the green room… and was bumped again. Tom was actually bumped three times by the Tonight Show. On his fourth scheduled appearance, while in make up, the show’s producer came and told Tom, “I’ve got bad news for you… you’re going on tonight!”

Now, keep in mind that in those days, fifteen million people watched Johnny Carson on any given night and a comedian could go from absolute obscurity to a household name overnight. After a single appearance with Johnny, Freddie Prince got a sitcom. Similarly, after that first appearance on the Tonight Show, CBS signed Tom on to a development deal. At the time, Tom had a wife and three kids and they were dead broke. They couldn’t even afford their $225 per month apartment rent. But that all changed after one performance on the Tonight Show. His contract with CBS included a $10,000 signing bonus and $1,850 each month for a year. Meanwhile, the William Morris Agency brought him on board and Sammy Davis Jr. took him on the road to perform for the next several years.

All from that first Tonight Show performance… and the years and years and years that it took to get to that point.

In fact, to close his five minutes on the Tonight Show, Tom said, “You’ve been a wonderful audience. Now, this is my first appearance here on the Tonight Show; and show business is a tough life, so if you like me and you’re Protestant, say a prayer for me. If you’re Catholic, light a candle. And if you’re Jewish, somebody in your family owns a nightclub… tell them about me!”

Amazingly, Tom never stopped working from that very day.

But, it wasn’t until Tom’s third appearance that Johnny finally called him over to the couch – the real sign that “you made it”.

Now, Tom “graduated” with flying colors from the school of hard knocks. But, he knew early on that if he was going to have longevity in show business, he would have to learn to work clean and make grandma and grandpa laugh just as much as the parents and kids. So, he learned to communicate without cussing or being too raunchy, which is also exactly what television executives wanted, which led to him being invited back time and again on late night TV.

Image: CBS San Francisco
Image: CBS San Francisco

One of Tom’s favorite stories, though, goes like this:

My son said something to me the other day that maybe you have said to your parents or thought at one point or another when you were arguing with your parents: “You know… I didn’t ask to be here”. Now think about it, when you say or think those words, first of all it puts you into a victim mode. And we are not meant to be victims, but victors! Now, I don’t want to give you a whole biology lesson, but when the male and the female make love, over five million seeds come from the male. 2.5 million of these die instantly and the other millions die along the way. Soon, there are only 100,000 seeds left, then 10,000… then only 100 seeds left… then five seeds left!… four… three… two… then it’s just you. So I told my son, “Don’t ever tell me that you didn’t ask to be here. That’s bull. You FOUGHT to be here!” And that goes for all of us. We’re all winners… from birth, as we beat those 2.5 million-to-one odds!

It’s all about having the proper perspective.

As Tom puts it, the message is too prevalent in today’s culture that we are all victims. And with this perspective, none of us has to take personal responsibility for any of our actions.

But, take Tom’s example: both of his parents were alcoholics; he shined shoes in taverns from the time he was seven-years-old until he turned twelve; He set pins in bowling allies; he caddied during his teenage summers; he sold newspapers… all to help feed his brothers and sisters. He can find all sorts of reasons why he should not be a success in life, or even an alcoholic himself. But, he realized that he needs to take sole responsibility for all his actions, as do all of us. When we adopt the mentality of victimhood, we voluntarily bind ourselves in chains and perpetuate the cycle instead of breaking those chains and become victors!

As a friend and follower of Tom, I can attest that I have never heard a negative, or victim-centric, comment from him. Tom is absolutely inspirational!

In fact, after seeing him simply introduce an act at Luigi’s Pizza in Chicago’s South Side, I was inspired to dive into a career in stand up comedy…without having a clue what stand up comedy even was!

In fact, when Tom was still performing with Tim Reid, they went to New York and heard about a place called The Improvisation. Now, this was before there was a single comedy club in Chicago, so a club where comedians got a chance to work out every single night was not a novelty, but an answer to prayer for Tim and Tom! It was at the Improv that Tom saw young comics recording themselves with their portable tape recorders and honing their acts every single night. That’s when it hit Tom and Tim – What if we had a place like this in Chicago?!

So, they went home and talked to the owner of LePub and asked him what his worst night of the week was… which was Monday. From there, Tom and Tim convinced him to allow them to do strictly comedy each Monday instead of the typical live-music acts. Tom then took to local radio and told everyone who would listen about Chicago’s first live comedy club. On their opening Monday night, there were lines wrapped around the block to get in!

And, thanks to Tom’s vision, comedy clubs like LePub and Comedy Cottage thrived and that’s where I got my nerve up to try to make people laugh! But I didn’t have a clue what I was doing. The emcee’s couldn’t leave the room since they didn’t know if I was going to do five minutes or five seconds. There were plenty of nights, in those early days, when I would walk out on stage and completely draw a mental blank.

My wife even asked me, “What on earth made you go back?!”

I replied, “I didn’t know if I was a sadist or a masochist, but someone in that room – either me or someone in the audience – was getting punished and enjoying it.”

Then, I remember seeing a fellow comic writing stuff down in a notebook and I asked him what he was doing. “I’m taking down notes so I can work on my routine”, he said. “You mean you don’t just go up and talk about your day?” was my reply.

I seriously thought that that’s all comics did!

I can honestly say that I couldn’t do what I do today if it weren’t for Tom and his bringing comedy clubs to Chicago when he did. He gave me a place to come back over and again, and endure the hard times, rethink my career choice, and grow as a comedian and a communicator.

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