Tom Dreesen- 2nd Interview, "The Man Who Made Sinatra Laugh" Show #267

Tom Dreesen, with a remarkable 55-year career in stand-up comedy, has established himself as a seasoned comic whose work continues to resonate from the 1980s to today. After being in the first Black/White comedy team in the 60's (Tom & Tim) and opening for Sammy Davis Jr., Tom is best known for his extensive tours as Frank Sinatra’s official opening act, Dreesen has captivated audiences in over 45 cities annually while also making more than 500 television appearances, including over 60 on "The Tonight Show." He attributes his enduring success to his passion for comedy, a commitment to moving forward, and the joy he finds in performing relatable material drawn from personal anecdotes. Beyond the stage, Dreesen actively shares his wealth of experience through motivational talks and by guiding aspiring comedians, remaining a vibrant and influential figure in comedy. 

(00:01:04) "The Man Who Made Sinatra Laugh" - A Comedy Legacy

(00:03:19) Flappers Comedy Club: Jay Leno's Legacy

(00:08:31) "Tom Dreeson's Evolving Bond with Sinatra"

(00:13:59) "The Man Who Made Sinatra Laugh" Show

(00:17:07) "Tom Dreesen's Mentorship Through Comedy Performances"

(00:18:38) Adapting Stand-Up Comedy for Online Platforms

The Education News Comedy Quiz -- Some of the Above
Play along with guest contestants from the education world. Laugh some & learn some...

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• 17:07 [Ad] The Education News Comedy Quiz -- Some of the Above
• 17:57 (Cont.) Tom Dreesen- 2nd Interview, "The Man Who Made Sinatra Laugh" Show #267

Transcript

R. Scott Edwards: 0:04

This is another episode of stand Up Comedy. Your host and emcee celebrating 40 plus years on the fringe of show business. Stories, interviews and comedy sets from the famous and not so famous. Here's your host and emcee, Scott Edwards. Ladies and gentlemen, welcome back to the podcast. It's another amazing interview on the stand Up Comedy. Your host in MC podcast. I am so proud to have back on my show one of the best comics ever. I mean, he's been around for too many years to think about, but let's get him on the show and then I'll kind of go over everything and catch you guys up. Ladies and gentlemen, please welcome back to the podcast, Tom Dreeson. Tom, to get you on the podcast twice just feels like so honored. Thank you so much.

Tom Dreesen: 1:02

I'm happy to do it. I had fun the last time.

R. Scott Edwards: 1:04

Well, we got a chance to talk about your early days in Chicago and some of your work, but let me catch the audience up real quick. Tom Dreeson is famous for so many things, but I'm going to mention just a couple. He was the official opening act of Mr. Frank Sinatra for many, many years. He also authored a book recently called Still Standing. We'll talk about that. But he's had over 500 TV appearances. He did over 60 spots on the Tonight Show. He was on Letterman a lot and co hosted a lot. He is one of the premier stand up comics of the 80s, 90s, 2000s and beyond. And it's just so exciting to get a chance to chat with you again. How you doing, Tom?

Tom Dreesen: 1:47

I'm doing real good. Doing real good. This is my 55th year in show business.

R. Scott Edwards: 1:53

Wow.

Tom Dreesen: 1:53

And I'm still out there doing it. I'm having a lot of fun. And oftentimes when I'm asked like, what's the secret of longevity? It's quite simple. Just keep moving, keep moving. But also, if you're lucky that you found the work that you love and you can continue doing it into your senior years, then that's the blessing of them all. And I found the work that I love many years ago, 55 years ago. And to be still doing standup and going out there on the road to my one man show is one thing. But when I come off the road, I go over the Comedy Store. Bill Burr and Sebastian Maniscalco and I are on sometimes there. And then I go over to the Laugh Factory in Hollywood and the audiences are young and my material still, I can still write material that relates to the younger generations as well. So that's what's so exciting in my life and why it's fun to get out of bed every morning, you know?

R. Scott Edwards: 2:43

Well, you are so correct, sir. We're talking about an industry, stand up comedy, that we've both been in for over four or five decades. And it is one of those great institutions where when you love your work, you can do it forever. Historically, somebody like George Burns really sets that in place. But even more recently, Jerry Seinfeld and Jay Leno, who have more money than God, are still out there getting into clubs, getting into concerts and doing comedy every week because they just love this industry, this art form.

Tom Dreesen: 3:19

Just about two weeks ago, I worked with Jay over at a club called Flappers in Burbank. You know, he goes there every weekend. He's like, loyal to that club for some reason, but so he goes there every weekend and I go there on occasion. I'll drop in and do a set and then Jay and I talk afterward because I've known him for almost 50. Over 50 years. I met him when he was in comedy. About four months I was working at the Boston Playboy Club in a comedian named Mike Preminger. Brought Jay there and introduced him to me. And he had a big goofy hat on. He had glasses, real thick glasses. He'd been doing stand up about four months at that time.

R. Scott Edwards: 3:57

Well, I had a chance to work with Jay. He came to work for me still early in his career. He was already headlining. But not only did he work my chain of comedy clubs, but I was able to do a couple large sold out concerts with him. And, and then he kind of just went beyond me. I was a stepping stone in his very successful life. But what's interesting is about the people that we have interacted with in the beginning. Now I referenced that you spent decades working with Frank Sinatra, working some of the best rooms, some of the best shows around the world. But we didn't touch on in the first conversation that you also must have had a chance to kind of hang out and be friends with people like Dean Martin and Sammy Davis Jr. The, the rat Pack group. There was a lot of celebrity and politicians in Frank's universe. Was that exciting, intimidating, fun, all those things?

Tom Dreesen: 4:56

I, I toured with Sammy Davis for three years as his opening act before I ever met Frank. Oh, and Sammy. Sammy would, Would tell me stories about Frank and how much he knew I was a fan, but. And he would tell me how much he admired Frank and what Frank did for him and how Frank broke down the racism in Las Vegas where he told them, if Sammy can't Stay in the hotel, then I can't stay there either, you know, because at one time, black acts could go work in the hotels back in the 50s and stuff, but they had to stay. Sammy called it Colortown. They couldn't stay in a hotel. They had to stay in a town, what they call Colortown. And Frank put a stop for that, as well as other things. So Sammy really adored Frank and told me a lot of stories. And I did the Dean Martin roast. And you mentioned George Burns earlier. I actually was on the roast with George Burns one time, or we were roasting him, but I did the Dean Martin roast, got to know Dean and played golf with him and did some shows with him, a couple corporate things, and really liked him a lot. I liked Dean a lot. And his family and I are still real close, his children. I introduced him, his one daughter, Gail, to her husband. He just passed away recently, but so I've known the family and. Yeah. And as far as intimidating, when you're touring with a guy like Frank Sinatra, and I think I explained this to you the last time we interviewed, you have to think what your job is. You know, there's 20,000 people in an arena and in Hawaii, 40,000, and who all came to see him. And you got to go out there. And I'd say, scott, I think I may have told you this last time, but embarrass, repeating. I'll say, scott, it's five minutes before show, before showtime. We're here at the, say, Nassau Coliseum in New York. I say, Scott, there's 20,000 people out there. I want you to go out there for the next 40 minutes, Scott, and stand in the center of that arena where they're all around you. Not presidium or out in front of you. They're all around you, 20,000 people. And I want you to hold their attention for the next 40 minutes, Scott. Oh, one more thing, Scott. I want you to hold their attention, but I want you to make them laugh for the next 40 minutes. And one more thing, Scott, I want you to make them laugh. When you want them to laugh, I want you to pull the strings and the emotions of 20,000 people. No props, no trick, no charts, no special arrangement, no special lighting, no orchestra. Just you and 20,000 people. And one more thing, Scott, not one of them came to see you. That's what was intimidating. And then, you know, we did shows at the White House. I mean, wherever you went with Frank, wherever you toured with Frank, whatever city you were in, the who's who of the governors, the politicians, you know, heads of state, heads of mafias, you know, in that room were all the power brokers. And so every night you walked out on stage, you know, and sometimes, like, staying in his home, you know, I'd stay in his home like five, six times a year. And the house guests, he had all these bungalows. The house guests would be Gregory Peck and his wife. Bernie could be Kirk Douglas and his wife, and Jack Lennon and his wife Felicia would be Clint Eastwood and whoever he was dating at the time and Robert Wagner and Joe St. John. And these are people I saw in the movies. When I was a little boy in Harvey, Illinois, I saw these people in the movies, and now I'm sitting at a dinner table with them.

R. Scott Edwards: 8:08

Wow, that would be. You know, that would be intimidating to me. Obviously, you spent many decades in that world, and I'm sure you weren't specifically starstruck, but out of all those celebrities and politicians were. Was there even one person that kind of set you back or you maybe wanted an autograph from?

Tom Dreesen: 8:31

You know, I mean, it would have to be Frank because, you know, he was so larger than life. But I never. The reason I stayed with Frank all the years I did, he never knew how much in awe of him I was because I never let him see that. I was a bartender before I was ever in Siblings, and I picked up on personalities a lot. I worked in two neighborhood bars, and I. Just. The moment I met him, I picked up on him. He didn't want another fan. He didn't like people gushing over him, you know, so he didn't want another fan. He wanted a friend. And that's what I. I was. You know, first I was. He was the boss of this magnificent tour, and then he was like a buddy. We hung out late at night. He stayed up till dawn every night. He never went to bed till the sun came up. And then toward the end of his life, he was like a father to me and gave me a lot of advice, and I spent a lot of time with him. I was a Paul Beer at his funeral, and I spoke at his funeral. And I miss him every day of my life, Scott. That's for sure.

R. Scott Edwards: 9:27

Well, I think it's incredible and really amazing for you to have met and worked with all those incredible celebrities and politicians. And the one person that you were always in awe of was the one you were opening for in and best friends with, Mr. Frank Sinatra. That's amazing. And ladies and gentlemen, there's a lot of amazing stories in Tom Driessen's book Still Standing. And if you haven't had a chance, go to Amazon and pick it up. Tom, could you tell everybody a little bit about Still Standing?

Tom Dreesen: 10:00

The subtitle is My Journey from Streets and Saloons to the Stage and Sinatra. And it's my journey from the beginning. I had eight brothers. It's a triumphant book and that's why it's got over right now. Over 455 star reviews on Amazon. I'm really proud of it because even to this day people are still buying the book. And I put it out a couple of years ago, but it's a triumphant book. There were eight of us kids in a suburb on the south side of Chicago, Harvey, Illinois, and we lived in a shack. Rat infested, roach infested shack. If you holes in your shoes, you put cardboard in it. If a window book, you stuck a rag in it. You know, we didn't have a bathtub. No bathtub and no shower, no hot water. And from a very early age I sang shoes in Caverns, I sick pins in bowling alleys, I cattied in the summertime. I sold newspapers on the corner, all to help feed my brothers and sisters. And none of this do I regret. So that's all in the book. Because I came from a neighborhood where in those days there was no such thing as welfare. The mantra in the neighborhood is you only deserve in life what you work for. That's all you deserve in life is what you work for. And so that was the mantra. And in those days. And so us kids went out very early in life and you know, made money, you know, to help bring money home to the. Help feed the family. So and that's what the book is about. It's my. And then all my rejections in my four years in the military and coming out and all the problems of wife and three kids and going from job to job and never finding who it was and then finally getting in the show business and realizing this is what I was put on the planet to do to make people laugh. And then there were still rejections. As you know, Tim Reed and I were America's first black and white comedy team history shows. We were the last. There was never one after us. For six years from 1969 to 1975, we toured the north and the south as the first black and white comedy team that was in the Jim Crow south. But even up north there were people that really wanted us to succeed and there were people that didn't because there's a Game people play in our societies called divide and conquer. And some people do not like seeing us get along. If we worked an all black club where there was a black guy who hated white people, hated him with a passion, he wasn't mad at me, he was mad at Tim for being with me. If he worked at all white club and a redneck hated black people, he wasn't mad at Tim. He was mad at me for being with Tim. So we put up a lot of that kind of nonsense. But you know, that's in the book and so many other things. My journey to finally getting on the Tonight show, which changed my life in 1975. Wherever you went in America, people said, what do you do for a living? You say, I'm a stand up comedian. The next question out of their mouth was, oh yeah, have you ever been on Johnny Carson? If you haven't been on Johnny Carson in those days you weren't considered a comedian. You might want to be one. But you know, because one appearance on that show, Scott, and your life changed. 28 million people watched that show. Cody Prince did one show when he got a sitcom the next day. I did one show on cbs, signed me to a development deal the next day.

R. Scott Edwards: 13:03

Well, and you ended up doing 60 appearances on the Tonight show. So I think you're proof positive. First off, I love the fact that your story and your book is all about a merit based life. You earned everything you have. You went from a shack to Sinatra. That is incredible journey. It didn't happen overnight. It took a lot of hard work and perseverance and, and it took a lot of dedication to who you are and what you wanted to do. And I think that's an incredible story and everybody should go out and it's still available. It's very affordable. Go get the still standing book on Amazon from Tom Driessen. But Tom, all those years in show business and now you're retired, but you're still getting out and doing some shows at Flappers and a few other clubs. Is this something that you are making a point of doing every week or once a month? How much comedy are you still doing?

Tom Dreesen: 13:59

I'm not retiring. I've never retired and I never will retire.

R. Scott Edwards: 14:02

I didn't mean to insult you.

Tom Dreesen: 14:04

Oh no, no. But I don't blame it because people might ask that because I'm not on national television much anymore. But I do a one man show called the man who Made Sinatra laugh. It's a 90 minute show that I do in theaters around the country and it's Stand up comedy. You know, I would rather work theaters than comedy rooms because theaters people have their drinks out in front, they come and they sit down and they're all right there in the palm of your hand. You know, there aren't waiters and waitresses roaming in out of the aisles and all that, you know, and such a great venue to work. But instead of comedy, the theater goes dark and a screen comes out. And Dennis Farina, God rest his soul, introduces me on screen and all the things I've done up to this point. And then I walk out, I do about a half an hour stand up comedy. Then I segue over to a bar on the stage that has a bottle of Jack Daniels on it. And of course, was Frank's drink of choice. And I tell a funny story behind the bar. Like I'm a bartender and all the lights go out. When the audience is laughing, all the lights go out. And on the screen, Frank is singing to me. I'm behind the bar. It's quarter to three. There's no one in the place except you and me. You know, it's one for my baby. And when he gets to the chorus, he goes off screen and spotlight hits me. And now the audience is in a bar with me and I've come home. And I tell him, the first time I heard that voice, I was 10 years old, shining shoes in a bar in Harvey, Illinois, and he was on the jukebox. Then I take the audience from that little boy hearing Frank Sinatra on the jukebox in Harvey, Illinois, to one day carrying his coffin out of a church in Beverly Hills, California. And as I'm telling stories, pictures are coming on the screen authenticating the story and video of Frank and I. So it's really. It's all about the Tim and Tom years and the Tonight show and touring with Sammy and Dean and finally getting to Frank. And then I close with. I take him to the funeral and sometimes have him in tears. And then I close with a very funny monologue. And I end it with a. There's a shot of Jack Daniels between you and I. It's iced tea. Cause I don't drink, but I'll toast him. I'll say, I wish for all of you what Frank Sinatra wish for you. The very last song that he ever sang is that the best is yet to Come. Good night, everybody. And you hear Frank Sinatra singing the Best is Yet to Come as you're leaving the theater.

R. Scott Edwards: 16:15

Wow. Well, you pretty much just synopsized the whole show, but it's incredible. Tom on not only have you touched the audience with comedy and humor as you always have, but with this final one man show, you're bringing some emotion, sensitivity and engagement with the audience. And I just know it's going to be heartfelt and touched. That's incredible. Ladies and gentlemen, if you see it coming to a city near you, the man who made Sinatra laugh, Tom Driessen's one mad show. It's a must see. Well, Tom, you seem to constantly be busy between your gigs and your book and your one man shows. Is there any gigs or special projects coming up in the next year? Let's say six months to a year that on top of this or are you just the one man show is your focus?

Tom Dreesen: 17:47

Well, I also give motivation talks to corporate America and at universities and I do a special one for comedians called the Joy of Stand Up Comedy and how to get there. But I talk on four subjects. Perception, visualization, self talk and develop a sense of humor. And I elaborate on those four points and then I have a Q and A afterward. And so I'm doing that. In fact, there's a place in North Hollywood now called Comedy Chateau and they just, they're having a big comedy festival where comedians come from all around the country, wannabes mostly. And they have a week there and I'm gonna do a stand up for them and then I'm also gonna give a motivation talk to them. That's next like in about two weeks.

R. Scott Edwards: 18:32

Wow, that's incredible. So it's not a TED Talk, it's a Tom Talk. And you get a chance to share some of your wisdom and experience to both enlighten and educate. Maybe the next group of comics coming up through the entertainment ranks. And as you pointed out, it is never an easy road. Well, Tom, it is so special to get a chance to share some of this with you. You have your one man show, your book still standing, your amazing history with Frank Sinatra. Thanks so much for sharing all this we with my audience and if it's okay with you, I'm going to share a little bit of your stand up comedy. At the end of this, I won't pull the gig that you did at Motel 6 if that means anything.

Tom Dreesen: 19:18

You know, when I go to Laugh Factory and now the Comedy Store does it, they film you and so does a comedy chateau. They'll film your set and before you get home they'll send it to you and then you can take two minutes off of that or a minute and put it on Instagram or TikTok. And a while back I There was a young audience and I wanted to prove this. Some friends of mine that I said, this is two jokes that I wrote in 1977 and 78. And I went up on stage and I did it and got a huge laugh and I put it on the Instagram. It got over 2 million hits, like 78,000 shares or something like that. And my point of that is I always have to tell people who do not know our business and even comedians, there's no such thing as an old joke if you've never heard it.

R. Scott Edwards: 20:05

That's so true. My answer to that, Tom, is I use material old and new, and to me, trying to entertain an audience, the key phrase is funny, is funny true.

Tom Dreesen: 20:22

I don't know how many times I have to explain this to people all the time about that. There's a brand new audience every two years, you know, and every two years there's, you know, another group in there. You know, you see kids today, 19, when they're 21, they're going in the club. So all you have to. There's. There is only one rule in comedy, and you just expressed it. There's one rule in comedy, be funny. And that's the only rule you have, you know.

R. Scott Edwards: 20:46

Okay, I'm going to put you on the spot. Tom, do you remember either one of those jokes?

Tom Dreesen: 20:50

Oh, sure, yeah.

R. Scott Edwards: 20:51

Go ahead and share the joke from 1977.

Tom Dreesen: 20:56

One of them was I said, my wife, I'm talking about my ex wife. We used to argue about the downest things. I once said, what would you do if I won the lottery? She said, I'd take half and I'd leave you. I said, I won $12. Here's six. Stay in touch. That's on Instagram. And then with it. I think the other one was that. Oh, I will say my wife did try to save the marriage. I came home one day, she was stark naked. She said, tie me up and you can do anything you want. So I tied her up and I went to play golf.

R. Scott Edwards: 21:30

Well, that is perfect and a great way to segue into your material. Mr. Tom Dreeson, always an honor to talk with you. Thank you again for coming back on the podcast. Ladies and gentlemen, stay tuned. I'm going to have a little bit of great comedy material by Mr. Dreeson. Tom, thank you so much for being on the show.

Tom Dreesen: 21:49

Thank you, Scott. Anytime, anytime you want me, I'm available.

R. Scott Edwards: 21:52

Great. Ladies and gentlemen, get his book still standing. Look for his show, the man who made Sinatra Laugh. And if you're in Southern California, he appears once in a while at Flappers and a couple of the other clubs. Keep an eye out for the one and only Tom Dreeson. Thanks, Tom.

Tom Dreesen: 22:08

You're welcome, Scott. And by the way, they can go to tomdresen.com that has all the information that they want on me.

R. Scott Edwards: 22:14

Oh, that's great to know. Tomdrason.com. thanks, Tom. I'm glad we got that in there.

Tom Dreesen: 22:19

Okay, buddy, talk to you soon.

R. Scott Edwards: 22:21

Ladies and gentlemen, here's a little bit of comedy by Tom Dreeson.

Tom Dreesen: 22:30

I have a 32 year old daughter I'm very proud of because she's so independent. She lives by herself in my house. She's got turtles all over her house. I think turtles might be the one dumbest pet a human being can have because, you know, you can't tell if a turtle's dead or alive. A turtle will lay in one place for 10 days, and just when you're ready to throw it out, it'll make a move. I have a son just like that. The Heights had a little place and they still had a little place called the Hill. When I was going up the hill, yeah, 55,000 Italians, three families saw one of my teachers, he said, you don't remember me, but I said, yes, I do. Your name is Richard Bruno. You teach algebra. He said, that's amazing. I said, listen to this. X to the fifth power times X to the fifth power is X to the tenth power. Because in algebra, you don't multiply exponents, you add them. He said, that's incredible. I said, you know, this is incredible. That's the first time I've ever been able to use that since you taught it to me. If you played a word association game with me when I was growing up in Harvey. If you said tall, I'd say short. If you say black, I say white. If you said show business. I said, Frank Sinatra, Dean Martin and Sammy Davis Jr. And the vice president of Harrah's Hotel, a man named Holmes Hendrickson, very powerful guy in Jose saw me and he was talking to a guy with a cigar. He said, tommy, come here, come here. I went over and he said, tommy, this is Mickey Rudin. Well, I recognize your name. That was Sinatra's lawyer. He said, mickey, this is Tom Grieson. And I think Tom would make a great opening act for Frank Sinatra. So they called me and they said, you know, a week later, would you like to work one week with Frank Sinatra? And I thought, this is going to be fun. And the second night I was with him. We went out to dinner and he laid down his knife and his fork in the middle of the meal. He said, I like your material and I like your style. I'd like you to do a few other days with me if you're interested. And I didn't say, let me check my calendar. I said, yeah, yeah. And it turned into 45, 50 cities a year for almost 14 years, whether on the road or off the road. Frank didn't go to bed till the sun came up. And like I say, he wanted you. And that was fun for the first 10 or 12 years. But, you know, one night we landed in Fort Lauderdale. Squad cars and limousine rushed us to this hotel. Frank went inside, he went to street to the lounge, and I tiptoed out of the car and I went up to my room. I thought, great, I can play golf in the morning. I was in my room, I wasn't there five minutes. I heard. I opened the door and it's a big redhead bellman, looked like a linebacker. He said, Mr. Dreason, Mr. Sinatra wants you downstairs in the lounge. I reached my pocket, I pulled out $20. I said, could you tell him you couldn't find me? He said, Mr. Sinatra gave me $100 to tell you he wants. Frank was a big tipper. Frank gave you $100? Whatever. If you bought him, you got $100. He didn't show off. He'd slip it to you. You brought him a pack of cigarettes, you got$100. He was coming out of Maison restaurant in Los Angeles one time, then the valet parker pulled his car up and Frank said, what's the biggest tip you ever got? And the kid said,$100. And Frank gave him two $100 bills. And Frank said, by the way, who gave you $100? He said, you did last Friday.

R. Scott Edwards: 25:41

We hope you enjoyed this episode of stand up comedy.

Tom Dreesen: 25:44

Your host and emcee. For information on the show, merchandise and.

R. Scott Edwards: 25:48

Our sponsors or to send comments to Scott, visit our website at www.standupyourhost and mc.com. look for more episodes soon and enjoy the world of stand up comedy.

Tom Dreesen: 26:01

Visit a comedy showroom near you.