7 Questions

7 Questions with Dennis Regan

dennis regan hires - 7 Questions with Dennis Regan

by Ryan Meehan

When Dennis Regan was young, he was on track to fulfill his dream of becoming an NFL quarterback.  Unfortunately, he blew his knee out when he was in kindergarten when he came down a little too hard on the teeter totter one spring afternoon.  Right then and there, he realized that he was going to have to find another way to make a living.  He reassessed his skills and asked himself “What am I good at?  What do I like to do?”  The answers came easily:  He liked daydreaming, goofing off, staring out the window, and cracking up his friends.  Actually the part about wanting to be a quarterback is not true, and his knee is fine.  The true story might not be quite as fascinating, but here it is:

He is a comedian.  He hasn’t always been – He started doing stand-up comedy in his early thirties.  Before that he had many different jobs:  Bussing tables, bagging groceries, killing bugs, throwing luggage, painting houses, and working construction just to name a few.  He hit his first open mic at Coconuts Comedy Club in North Miami in 1987, where he did “okay”.  Four months later, he won a local contest and within a month a club owner was paying him $30 for a ten minute set every weekend.  The next year he moved to New York City, started to do late night shows, and began to break into the main line-up of all the important clubs:  The Improv, The Comic Strip, The Comedy Cellar, Catch a Rising Star, and Dangerfield’s.  From there he went on to appear on television dozens of times:  He’s had multiple appearances on The Late Show of David Letterman and the Tonight Show with Jay Leno.  He’s also been on Showtime and Comedy Central, and you probably would have seen him there if you didn’t have eight hundred channels.  I am delighted to have Dennis Regan as my guest today in 7 questions.  

RM:  What was the first comedic performance you saw on television that led you to the realization of stand-up comedy as a legitimate form of entertainment?   At that point in time did you think that it was something you could see yourself doing; or was it not until years later that you actually had the thought that this might be something that you’d like to try?

DR:  When I was a kid, it never occurred to me that I might grow up and be a comedian. Not even in high school. It wasn’t until I was 33 years old that I decided to go to an open mic night. And not until about six months later that I was pretty sure I could do this for a living.

RM:  Why do you think that you’ve never been to Arkansas?  Isn’t there a comedy club in Little Rock?

DR:  Arkansas is the only state to which I’ve never been. I would like to visit Australia so I could say that Antarctica is the only continent to which I’ve never been. I’d love to hear from a club in Little Rock… or Perth.

RM:  When you watch video clips of yourself performing, which facet of your delivery to you tend to be the most critical of and why?  Do you think that will ever change?

DR:  I find it hard to watch videos of myself shortly after a performance. I’m hyper critical at that point. But after a little time passes, a year or two, I tend to just think, “that was pretty good.” After more time passes and my skills have advanced further, it becomes difficult again. I tend to cringe.

RM:  Which of your television appearances was the most nerve-racking and why?  What did you do to calm those nerves and focus on the task in front of you?

DR:  Although I’m very happy that I’ve been able to do some of the big shows like Letterman and Leno, those sets really aren’t as much fun as your regular club sets or corporate shows. They’re exciting, but if you flub one line, you’re screwed. If you flub a line in a regular show you just laugh it off and move on.

RM:  Let’s say hypothetically that I run a successful corporation and we are looking to hire a comedian for an event that we are having.  How would you sell yourself to me without using information from your bio or testimonials from previous corporate gigs?

DR:  I’d say, “I work squeaky clean and I’m very fucking funny.” Actually, I find it extremely uncomfortable to blow my own horn, especially to get a gig. It’s much better to let an agent do that. But since you asked, one thing I’ve gotten quite good at over the years is personalizing a show with crowd work. I don’t really do any advance prep work or anything. I just talk to the people in the crowd and it usually turns out to be a lot of fun. Also, I have plenty of material that works well with corporate crowds whether they be younger or older.

RM:  Which aspect of joke construction do you think is the most critical in order to really generate a good laugh?  When writing new material, do you start from that point and work outwards; or do you construct most of your bits chronologically starting with premise and working though all the way to the punchline?

DR:  It always starts with the premise. It will occur to me that there is something funny about this or that. The challenge is coming up with a precise way to express that to an audience through a bit. What’s the best wording. This may seem obvious but it’s the hard part.

I’ve never read a book about joke writing. I’ve always preferred to think of it as more of an art than a science. But there’s no denying there’s a science to it. One mistake most newer comedian make is they are too wordy. Brevity, really is, the soul of wit.

RM:  When you work colleges and cities with debaucherous reputations such as Vegas and Atlantic City, are you ever heckled by audience members who are expecting more of a raunchy act?  If so, how do you usually deal with that?

DR:  First of all, I don’t find the audiences in Vegas or Atlantic City to be like that at all. I love doing shows for people that are on vacation. It’s a good vibe. But I have come across crowds like that. One time I got heckled, “Be more vulgar.” I responded, “Fuck you.”  Not very clever. But vulgar. And pretty funny. The truth is, that over the years, my act has gotten strong enough that they don’t even notice that I’m not being dirty.

RM:  If all comedy audiences were relatively the same and were not offended by any sort of dirty language, do you think that you would still work clean?  What is the main reason that you have chosen that path for your career in comedy?

DR:  I wouldn’t say I’ve chosen any path to work clean. And I don’t always work clean. I guess I work clean 98% of the time. But I never promoted myself as a clean comedian until I started tapping into the corporate market. In general, I’m not worried, in the least, about offending people with language or material. I just work the way I do because of the way I feel about comedy and about using the language creatively. I just think of it as part of my style.  After people see my show, I want them to feel like they don’t have to run home and take a shower.

RM:  What’s up next for you in the remainder of 2015 and beyond?  Anything big in the works that we should know about?

DR:  My calendar these days is filled with corporate gigs, small theaters, and cruises. I work very few comedy clubs anymore. My primary project right now is a soon-to-be-launched web-series called That Darn Dennis.

Official Website:  http://www.dennisregan.com/

Dennis on Facebook:  https://www.facebook.com/pages/Dennis-Regan/147424318628419

Dennis on Twitter:  http://twitter.com/thatdarndennis

Once again thanks for visiting First Order Historians and enjoying more of the internet’s finest in user generated content.


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