Inspire. Educate. Entertain.

Conversations featuring authors and influential leaders in the arts, media and business.


According to Tom Dreesen, there's one essential rule for stand-up comedy: be funny. He's quick to add something he learned from Sammy Davis Jr. -- you can't make everyone love you -- which he says, particularly applies to comedians. And, if you are thinking about writing jokes, it helps to know that the setup line has to hide the punchline, that there are no "victimless" jokes, and, according to Mort Sahl, someone is always wrong.

The deeper we go into it, Dreesen imparts a dozen gems about the evolution of an extraordinary career in comedy richly earned, from the process of developing an ironclad six minutes for The Tonight Show, to a who's who roster of influential personalities. After 48 years in show business and counting, including 14 years on tour with Frank Sinatra and over 60 appearances on the Tonight Show, Tom Dreesen still maintains a very busy schedule of personal and promotional appearances, stage shows and charity events. 

There is much more, as you will hear in our July 28th CONVERSATION, about the passing of Barbara Sinatra, the legacy of Johnny Carson and the early days, teaming up in 1969 with Tim Reid for Tim and Tom, the first -- and last -- black and white comedy team.


The Tim and Tom Show … “The very first time I went on stage was September 1969 … with Tim Reid. We were America’s first black and white comedy team and history shows we were the last. We did it for six years … we struggled… America was in turmoil and we were going to make them laugh to make them forget about their troubles."

How to Write a Joke … “In comedy, if you dissect it, it gets boring but let me say this … when you are writing a joke, comedy is two things: number one, it is nine tenths surprise. The audience laughs because they did not think you were going to say that or do that. So, the setup line has to hide the punchline, and the other rule is there are no "victimless" jokes. Who is the victim in this joke? Is it me, society, the government, the airlines? Someone has to be the victim in this joke.”

On Barbara Sinatra … “She was always a good friend to me … She and Frank always opened their home and hearts to me and I will miss her… If I could speak for God  -- and I can because I talk to him all the time -- I would say that God is going to say to her when she arrives at the pearly gates that some of my children came to you in severe pain and you never turned them away, so, I am not turning you away.”

Working Blue … “In comedy we call it ‘working blue’, when you work dirty … I am working at the Laugh Factory a couple weeks ago trying out some new material … Around the corner … two of the young comedians did not know I was there and were talking about me. One said, ‘You know Tom Dreesen is here. He is old school.’ The other comedian said, ‘Old school what do you mean?’ ‘He doesn’t use the F-word’ and the other comedian says, ‘He doesn’t use the F-word? What does he use for adjectives?’ ... and I stuck my head around the corner and I said, ‘Adjectives.’”

On Frank Sinatra … “He was larger than life … I used to say to be an opening act for Frank Sinatra was like when I was an altar boy, if I had to serve mass for the Pope. I wanted to follow it for as long as it would take me and it turned into a great friendship … This kid from Harvey with holes in his shoes, shining shoes on the floor of every tavern in Harvey and on the jukebox was Frank Sinatra, Dean Martin and Sammy Davis Jr.  and then years later I flew with them and performed with them … an amazing time.”  




Copyright 2019

Roxbury Road Creative, LLC

Powered by Squarespace