An Examined Life with Jeff Allen 47: The Tonight Show, The Improv & the Early Days of Chicago Comedy with Tom Dreesen Frank Sinatra’s Theology & the Downfall of America with Tom Dreesen

An Examined Life with Jeff Allen 47: The Tonight Show, The Improv & the Early Days of Chicago Comedy with Tom Dreesen Frank Sinatra’s Theology & the Downfall of America with Tom Dreesen February 22, 2016


Tom Dreesen is the main reason that I became a comedian. In Chicago, he’s known as the “Godfather of Comedy”. In addition to appearing on the Tonight Show with Johnny Carson multiple times, as well as the Late Show with David Letterman – where he also guest hosted from time to time – Tom opened for Frank Sinatra for over a decade.Tom Dreesen

Tom was working with Smokey Robinson at Caesar’s Palace in Lake Tahoe and Frank was performing next door at Harrah’s. So, one night, without even changing out of his stage clothes, Tom raced over to Harrah’s to hear as much as he could from Sinatra. As Tom puts it, Frank could create more excitement by simply walking out to the microphone than most people do in their whole lives.

As he ran toward the showroom, Tom was stopped by the Vice President of Harrah’s Hotel. Now, Tom didn’t want to miss a second of Frank’s show, but he also knew better than to blow off the VP of Harrah’s (and whoever the authoritative heavyset guy who was with him).

This is when Tom’s life changed forever (once again). The heavyset guy was Frank Sinatra’s lawyer. When the Harrah’s VP said, “I think Tommy would make a great opening act for Frank”, the lawyer rolled his eyes like he had heard that line a million times. But then Tommy saw the wink – a wink between the two big-wigs.

Then the lawyer said, “Hey kid… If I give you a week with Frank, would you want more than $50,000?”

Tom replied, “Sir, if you gave me a week with Frank, would YOU want more than $50,000?” which made both powerbrokers laugh out loud.

A week later, Tom received a call asking if he’d like to work a week with Frank in Atlantic City. Tom figured, if nothing else, he’d get his picture taken with the Chairman of the Board and hang it in every bar back home in Chicago. But, on the second night that they performed together, Frank and his wife took Tom out to dinner. It was over this delicious dinner that Frank put down his fork and knife and said, “Tommy, I like your material and I like your style. I’d like you to do a few more dates with me, if you’re interested.” Tommy didn’t even need to check his calendar before saying YES!

Over the next fourteen years, Tom and Frank performed at nearly 700 stops and became incredibly close friends. Tom actually was one of Frank’s pallbearers and spoke at Ol’ Blue Eye’s funeral.

Image: Carmel Magazine
Image: Carmel Magazine

Over the years, Tom got to see sides of Frank Sinatra that only legends are made of. For instance, his generosity overflowed, as he would scour local newspapers seeking people who were going through tough times and then anonymously donate money into their bank accounts. Frank was greatly influenced by Lloyd C. Douglas’ book Magnificent Obsession; and according to Tom, once you say to your Master, “Lord I want to be a  (fill in the blank)_” and you sincerely and wholeheartedly believe that 1) that is the desire of your heart and 2) the desire of your heart is within God’s will, then as the Bible promises, “Ask and you shall receive”.

As Lloyd C. Douglas prescribes, once you receive any blessings, you need to keep your eyes and ears open for opportunities to pass on those blessings to God’s less fortunate children. But, do so in secret, along the same principle as in Matthew 6:2-4,

When you give to someone in need, don’t do as the hypocrites do—blowing trumpets in the synagogues and streets to call attention to their acts of charity! I tell you the truth, they have received all the reward they will ever get. But when you give to someone in need, don’t let your left hand know what your right hand is doing. Give your gifts in private, and your Father, who sees everything, will reward you.

Likewise, if Frank ever read about a kid in New Mexico who was suffering from a brain tumor and living in a box car, the next day there would be someone knocking on that box car saying, “Your medical expenses have all been paid for”… and the person delivering that news had no idea who the benefactor was.

And it wasn’t just the destitute who Frank was generous toward. As Tom says, you always had to be careful when you hung out with the Sultan of Swoon, because if you simply saw a painting that you liked and mentioned it to him, he’d take it off the wall and buy it for you right then and there.

One night, Tom and Frank were leaving New York’s Waldorf Astoria Hotel out the back exit. As they were getting into their car, a woman who had been waiting for hours outside ran up and begged for an autograph: “Please, Mr. Sinatra… my husband is home sick and if I could bring home a signature of yours, it would mean the world to him.” Of course, Frank stopped what he was doing and began to sign his name for her. While he was writing his autograph, though, she noted how beautiful his cufflinks were (which they should have been – they were $2,000 cufflinks) and of course, he took them off right then and there and gave them to her to give her sick husband.

Tom asked him why he did such things and Frank replied, “Tommy, if you possess something that you can’t give away, then you don’t possess it… it possesses you.”

He simply didn’t care about material things, especially money. As Frank put it, “Aristotle Onassis was one of the wealthiest men of his era. But, the second that he died, all those riches were transferred, so he never really owned any of it… he was just using it for a time.” And Frank didn’t just talk this talk, he walked the walk.

Tom’s dad was an alcoholic and not much of a role model for him, so Frank’s modeling this kind of behavior and life lessons really filled that father figure void in Tom’s life.

And it’s this kind of inspiration that led Tom to the Illinois Fatherhood Initiative.

According to national statistics, three of every ten white children born in America are born without a father in the home. Half of all Hispanic children are born into the same situation. Yet, seventy percent of African American children are born today without a father in their home. All total, this equates to over 40 million children living in the US without a father at home. Couple those numbers with the fact that 77% of all teenage crimes in America are committed by fatherless teenagers, and you’ve got a very easy-to-diagnose problem.

We are creating a nation full of criminals, simply by fathers not being dads to their children. Once upon a time, no matter what type of neighborhood it was in America, if a man saw a teenager up to no good, they would take that punk-kid by the ear and return him to his father to deal with. However, today, there are no men like that in the neighborhoods anymore – no one to police their own – and the punk-kids are left to do worse than ever before. Instead, with the absence of men, the neighborhoods are filled with grandmothers taking care of multiple little babies who are not even hers, but her daughter’s, standing on the street corner trying to keep the gangs away from her grandchildren. However, she’s fighting with a broomstick and they’ve got an AK-47.

No one wants to admit it, but this is the downfall of America. It all began with President Lyndon B. Johnson’s “War on Poverty” in 1964. While it was well-intentioned, it actually incentivized single-parent families. It basically said, “If you are a struggling mom with one child and no father in the house, then the government will give you $250 each month. If you have two children, we’ll give you $500. If you have three kids, we’ll give you $750 each month. However, if you have a father living in the home, you don’t get any money.” What’s the sense in fathers staying home? As well-intentioned as it may have originally been, it has actually destroyed the fabric of America – the nuclear family structure.

Image: USDA
Image: USDA

Instead, the definition and rules of what it means to be a man has been morphed into something completely different and dangerous. Things like honor, commitment, honesty and integrity have fallen by the wayside and are more and more absent from our culture with each passing generation. They have been replaced with perceived power and strength, like street gangs front with – it’s almost Darwinian.

Personal responsibility is simply disappearing.

Tom is doing all he can to reverse this trend. As he has told his kids all their lives, There are only two things that you will ever be judged by: your work and your word. Therefore, take pride in your work whatever it may be and just as importantly, your word and integrity must be of the highest caliber!

This kind of mindset is what Tom and I were raised with – one that told young men that if they were to ever get a girl pregnant, they were to step up and marry that girl, or at the very least, provide for every need of their child. Because if he didn’t, then the family and neighborhood would be forced to and the men of the neighborhood wouldn’t allow that.

Then came LBJ’s plan and the government said, “Noooo… don’t worry about that, kid. You don’t have to be responsible for that child because we in the government will take care of all his needs, paid for by American tax payers.

To help buck this trend, the Illinois Fatherhood Initiative equip young men with tools and mentors that help change the tide and encourage young men to stay home and raise their children.

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