Dennis Regan, the older brother (by three years) of comedian Brian Regan, traded one family business for another.
He swapped the harsh sunshine of south Florida, where he and his dad owned an asphalt company called Tars & Stripes, for the darker recesses of comedy clubs, and found his calling.
Dennis, who’s opened for his brother as well as for Ray Romano and others, headlines comedy clubs around the country now. He's worked behind the stage as well. He wrote for the Kevin James comedy “The King of Queens,” from its sixth season to its ninth and final season.
All of it certainly beats the asphalt business.
I saw you and Brian together at the Paramount when he was taping his special. How often do you two work together?
I just started opening for Brian again after not doing it for a few years. It’s fun! I like Brian’s crowd and visa versa, I guess. It’s nice to do theaters once in a while. The audience is all facing in the right direction. No one is stuffing nachos into their mouths. The focus is great!
What made you decide to get into comedy, because originally you were in the asphalt business, right?
Well I did a lot of things before the asphalt business. It was just something I did for a short time. I was doing it when I started doing comedy. So it was an easy transition because I hated that asphalt business.
Was it Brian that inspired you to do stand up?
It was. I probably never would have gotten into it if he hadn’t. Brian started six or seven years before I did. I had never dreamed about being a comic. It was just one of those things you wondered about. I got to a point where I started doing things I was afraid of in my life, to challenge myself, and that was one of the things that I could do. You can go to an open-mic night for free and give it a try and that’s what I decided to do. Over the years, I had given Brian a few jokes. He’d come back and say, “Yeah, that joke kind of worked.” But his style was a bit different from mine. Sometimes he would keep them in his act but most of the time he wouldn’t because he had a different sensibility. I had a little bit of a – I wouldn’t say head start — but I had tried a couple of jokes through Brian over the years.
So you knew what would get a laugh and what wouldn’t?
No, it wasn’t that so much. When I started I had an idea that you needed punch lines and laugh points or whatever you want to call them. A lot of people, when they’re brand new, go up with rambling premises and haven’t really got the idea that there has to be some place where the laugh is supposed to be. At least I knew that.
Did Brian give you some pointers, once you decided you wanted to do this as well?
He did, but he wasn’t really around. He was in New York and I was starting in Miami. I’d call him up and I’d say I did this and I did that. When I look back on it, he was really – not just supportive – but very cool about things because when you’re new you don’t realize that some of the bits you’re doing may have been done a thousand times or a million times. I’d go, “Here’s this brilliant idea I’ve been doing” and he would let me find my way rather than going, “Oh, Jimmy Robertson’s doing that bit” or anything like that. He just kind of let me find my own way.
How hard was it the first time you went on stage? Or how easy was it?
It was hard. It was hard. In fact, I drank three or four glasses of wine. I’m not a wine drinker, but for some reason I decided some wine would help me up there. The second time I did it, I think I had two glasses of wine. Then I told myself if you need to drink to do this, then you’d better find something else to do. So I never drank before performing, really, again. On occasion I might have a beer or something like that, but for the most part I got away from it right then. The first time was hard, but I tell people who are thinking about trying to do comedy that you’re never going to wake up and say, “I’m ready to do it today. I am ready.” It’s not going to happen that way. What’s going to happen is you’re going to get up the nerve to just go and do it and it’ll be hard but you will have done it and you’ll know you can do it again. But you’ll never wake up and go, “I’ve got the confidence and the material and everything. Let’s do it.”
What was it about that first experience that made you want to do it again?
I got laughs. I got enough laughs the first time to think: “I’ll go back and do it again.” But it wasn’t a career thing. I wasn’t thinking I was going to be a comedian. I was just doing it for fun. And it was just fun. I was going up three, four times a week and doing my five minutes or whatever, and it was just fun. It wasn’t until one night when I’d been doing it about six months and there was a small crowd – about 16 people – and none of the other comedians had done very well, and I got up and I did well with this small crowd and came off and thought I might be able to do this. Because that is hard. That’s what you’re up against sometimes. The big crowds are actually easier, much easier, than the small crowds.
Why is that?
For a few reasons. Small crowds are uncomfortable. There’s pressure on them to laugh and they feel it. If you can make them feel comfortable, let them know that they can laugh or not laugh and it will be alright, there is much more chance that they will laugh. You have to finesse it too and make this stuff sound less like material and more like a conversation with a small crowd.
Were you going back to the same club when you were starting out?
When I started in Miami, Florida, it was 1987 and, at first, there was only a couple of clubs. Shortly after I started, a bunch of new clubs opened and there were six comedy clubs in the area: Two clubs in Dade County, two clubs in Broward County, two clubs in Palm Beach County. I was driving a lot, but I was able to get on stage three, four times a week. Clubs were open more nights back then. Five, six nights a week, Tuesday through Sunday, that kind of thing. And they all had open-mic nights. After about four months or something like that I had my first pay gig.
Where was that?
It was a club called Casey’s Comedy Club in Fort Lauderdale and I got $30 a set to do 10 minutes. And that’s what I did. I did one show Friday and two on Saturday and they gave me $90. I thought, “Damn! This is alright!”
But that wasn’t enough to live on. You couldn’t quit your day job at that point.
No, but I was headed that way.
Did it click in your head that suddenly you were a professional comedian?
What clicked was I would have done this for free, and I got paid for it. Most people say if you can do for a living what you enjoy, then you’ve won half the battle. I was starting to think in that direction.
When your brother Brian went off to college to study accounting and then decided he wanted to be a comedian, what was the family’s reaction to that?
I don’t remember any reaction to that. It’s not like we sat around the table and had discussions about Brian. He walked to the beat of his own drummer, even back then. I don’t remember being that aware of it. I do remember when he started going to the Comic Strip in Fort Lauderdale. I was very supportive of him. It was never my big dream, but it was his. I remember when I started a few years later. I was in the asphalt business with my dad. I decided I was moving to New York. I’d been doing both, that business and comedy, for about a year and a half. My dad was sort of depending on me and I said, “I’m gone. I’m out of here, Dad. I’m going to New York and I’m going to do comedy.” He said, “Dennis, if I could make a living telling people jokes, that’s what I would do.” That was nice. He was encouraging.
Are you all funny? Is there a Regan sense of humor?
We’re all pretty funny. Except for my brother, Jack. He’s never said one funny thing and he tries all the time. I’m just kidding. I don’t have a brother named Jack. My dad has a very good sense of humor and my mom does, too. My mom was always a tough crowd. She would laugh, but she wasn’t an easy laugh. If you got her to laugh, you did good.
What happened once you got to New York?
I moved to New York after only doing comedy for about a year and a half, and started trying to break into the clubs. It’s not easy. It wasn’t easy then, but I had pretty good success. You’d audition at 2:15 in the morning or 2:30 and some club manager would watch you and say you could do the 2 a.m. slot tomorrow night or Wednesday night and you’d be going up when the crowd was leaving or there’d be five people left. Then, after you did the late night stuff at a certain club for a few months, they might use you for the opening spot at 9 p.m., which was equally hard for different reasons. I had good success breaking into the clubs. You work yourself into the prime spots of the night, like the 10:15 to 11:15 spots when the crowds were all kind of good and I’d try to develop material and gain confidence.
What was wrong with the 9 p.m. spot?
Well, There might be eight people in the audience. I’m talking about the Comedy Cellar in the Village. The emcee would just do a bunch of crowd work. “Where you from?” “Staten Island.” “Australia.” And then he would bring you up and you couldn’t do any more crowd work because he had already done that and he hadn’t done any material so it was hard to do any material. It was hard to transition. You had to try to do material but make it sound like it wasn’t material. Kind of tricky.
What were you doing to support yourself?
I was just doing comedy. At the time I moved up there I didn’t have any money but I could get middle work at clubs around the city or in Long Island or in New Jersey. Or Connecticut. Upstate New York. You could get a hundred bucks a set and you could make 600 bucks for the week and you could do that a couple of times a month. If you worked at clubs in the city, the Cellar, Catch a Rising Star or the Comic Strip, you could make a few dollars on the weekend, too. I didn’t need much money. I rented a room in Queens that cost me $330 a month. A room in a house. It was not the Trump Plaza, just a little room.
Was there a point at which you said you could make a living at this and not go back to Tars and Stripes?
There was a point where I said I really enjoy this and I made the decision, if I could, for the rest of my life just do what I enjoyed. That’s not an easy thing to do. There’s times when I didn’t enjoy headlining. I would just middle because I found that to be more fun. That was a lot less money but I just wanted to do what was fun.
Is there more pressure when you’re the headliner?
There’s more expectation and it’s harder. The people in the clubs, they’re more tired, they’re more drunk and sometimes you have to follow somebody who isn’t easy to follow for a variety of reasons.
Who did you have to follow who was hard to follow?
Once in a while, there will be a comic who is just real hard-hitting and he might be funny but he doesn’t require very much of the audience. He doesn’t ask them to think at all. The audience doesn’t know it. They just know they’ve having a good time. Then when you go up and you want them to think a little bit, they’re not in that frame of mind. They can freeze up on you. It takes a while, sometimes, to get them to transition from that guy’s frequency to your frequency. Most of the time they come along with you, but sometimes they don’t.
When you’re opening, like when you opened for Ray Romano at Carnegie Hall, how exciting is it to be a performer at Carnegie Hall, even as an opener?
It’s fun. It’s fun. I mean, you would like it to be your name up there, the person that everyone came out to see and hopefully that’s down the road a little bit. Carnegie was a pretty cool opportunity and it’s a real cool house. It’s a nice credit to have been on that stage where so many people have been. A comedy audience that came out to see comedy in a place like that, it was great.
Do headliners give you any restrictions or advice before you go on?
No. For the most part you get the gig because they know what you’re like. They know you’ll set them up well. That’s why you got the gig. No, I’ve never had anybody say do this or don’t do that. But if a guy does a bunch of married material, I just won’t do mine. I won’t burn that stuff for them. That helps me get those sorts of gigs. It’s also a matter of professionalism and appreciation for what they do. I don’t think that enough comedians think that way. When you’re the opening act your job is different from going out there to kill. Your job is to help set up the show.
What do you learn from working with other comedians who have been doing it longer and have had more success?
Starting out, I learned a lot from watching other comics. And I learned by watching them more than once. If there was a comic in Miami when I was new, I would go to the open-mic night on Wednesdays and then I would try go to back on Sunday to watch them. I would watch them both nights. The reason is on Wednesday I would just enjoy his act. I wouldn’t really get anything out of it. I would just enjoy it. But if I went back a second time and watched it, I would kind of go to school. I would see that he always looks for a lady with a big purse up front. Or he decided not to do that tagline for some reason. He decided not to do this bit with that crowd. You would learn things about the act in that way.
What about when you’re in the regular orbit of comedians, like when you were working on “King of Queens” and you were working with Kevin James and Patton Oswalt and Jerry Stiller and Ann Meara on occasion?
You mentioned the actors. I was around the actors some. I was around during the taping, but I was a writer. Most of my time was spent with the other writers. I learned a lot about writing. All the little things, the techniques and things like that. For the most part it was discipline that I learned there. It’s different from standup. With standup you might wait for inspiration. There it was: “You people go in that room over there and come back with some funny stuff about this or that. Come up with something for this scene or this character.” Then you would do it and you would come back with something.
How did you get that job?
They were looking for somebody to bring in. I think they interviewed a few people. And I got the job. I think they liked my standup. I think they had seen a set I did on “Letterman” which dealt with married stuff. Since that’s what the show was about primarily, that kind of got them interested in me.
Does your wife get veto power over any marriage jokes you tell?
Yeah. I wouldn’t want to do anything that upset her. I can’t think of anything that she’s vetoed to this point, but I try to find some balance so it’s not all just my point of view. Well, it’s all my point of view, but I try not to come across as being right all the time.
You mentioned earlier trying to get your mom to laugh, the competition between your siblings. Is there any competition between you and Brian as the only professional comedians in the family?
I think mostly we’re just supportive of each other. We give each other bits once in a while. I get advice from him when I’m going down a path that he has already been down. And if he needs somebody beat up, then I’ll step in and do that. But I wish, like most comedian do, that I was doing as well as Brian.
Did having him as a brother open any doors?
Maybe a few. Not too many. You gotta remember that when I was getting started, he wasn’t that much farther along. I mean, I might have gotten an audition at a club because he had worked there. But an audition is just an audition.
If you could rank on a scale of 1 to 10, and 1 is open-mic night and 10 is a household name in comedy, where would do you see yourself and where do you see Brian?
I get compared to Brian sometimes and I would rather be compared to the 9 million other comedians. Not too many comics are having the success that Brian’s having. In fact, I can’t think of any who are having the success Brian’s having without having a TV show. Brian’s built a base, an audience of people that love him, but he’s worked his butt off for a long time. I’ve done different things. The writing job took me out of standup for a few years. And I’m not sure how hard I want to work at it. I have a little boy and I like being home and it’s hard to get material working being out there one or two weeks a month. It’s hard to get that stuff going. Stand-up is not the kind of thing you can do into your 60s if you haven’t had some sort of significant amount of fame. If I don’t get a little more popular in the next few years I’ll probably find something else to do.
How do you make the transition from being on stage to writing, having to be funny on command?
The writing room at the “King of Queens” was a good room. It was the only writing job I had, but I heard other writers talk about rooms where it wasn’t appreciated if you threw out a less-than-stellar idea. I was in the type of atmosphere that allowed you to throw out any kind of idea you had — whether it was lame or just off the top of your head — without a lot of pressure. I think that’s important because even if your joke wasn’t that good, it might give somebody else an idea and that idea would be good. Where I was was a lot of fun and you could feel free to throw out whatever idea occurred to you. I really enjoyed my writing job.
You had to know the characters. Early on I would pitch a joke for, say, a character like Deacon as an example. I thought it was funny joke and it was, but it wasn’t something he would say. It wasn’t true to his character. I had to learn the ropes.
Was it hard writing for someone besides yourself?
Yeah, it’s hard. Because I was only used to writing for myself, things that I thought were funny, and here I am writing for these characters.
Having seen this side of a sitcom, would you want to be the front-and-center star of a sitcom?
I would like a part in a sitcom, maybe a supporting role. but at this point I couldn’t carry the ball like Kevin James did. There’s a lot more to it than people realize.
Are there more in the family who are going to be taking the stage?
My oldest brother, Mike, has gotten into Toastmasters. He’s always been intrigued by comedy. He’s been doing that and getting his laughs.
When you’re trying a bit out in your act, how many times do you try it before deciding to keep it? Is it a three-strikes-and-you’re-out rule?
That’s a good question. A lot of comics ask that question, too. It’s not an easy question. You can ballpark it around there, three times or something like that, but you would probably change it a little the second time. It depends on how well you told it the first time, how much confidence you have in it. It depends on how funny you thought it was. You probably wouldn’t go up and try it exactly the same way. If it starts to catch a little bit, you might think you have something to work on. And if you decide to lose it because it’s just not working, it should still stay in your notebook or in your head because, as you get better, lots of things come back and you look at it a few years later and you go “I know how to make that work now.” I’m also finding that for me, I have to give the audience a little bit more information than I had previously. That’s sort of the guesswork. How much do you want to give and how much they need to think? I’m finding I just need to give them a little more information. I’m finding that a lot of my stuff is working that wouldn’t have worked for me before.