Getting to Know Dobie Maxwell aka “Mr. Lucky”


1) I started out in a workshop and also did some open mics. So Dobie, how did you start out in comedy and which way do you feel is the most beneficial for a comedian to start out his/her career?

dobie-maxwellI started by going to an open mic in a jazz club in Milwaukee where I’m from. There were no classes or workshops when I started, and in fact I started one in 1993. I went to that open mic 57 weeks in a row before getting a paid slot at a local showcase where I received $10 for ten minutes. I stole that money, as I was horrible as most newbies are, but it was the start of a lifetime of performing all across North America in comedy clubs, colleges, corporate shows and cruise ships. I’ve pretty much done it all.

As far as starting out now, I would recommend anyone find a mentor. There are all kinds of “classes” taught by total idiots who have never been on stage a day in their life. It’s a cash grab, and it looks easy to prey on total newbies — and unfortunately it is. I would highly scrutinize any and all “comedy teachers” and make sure they teach from a position of experience. Other than that, I feel it’s a total waste of money.

One way or another though, find a mentor. I try to be of help to as many new comedians as I can, simply for the fact I know how much I appreciated it when someone helped me when I was starting. Not many did, but those who did are cherished in my mind to this day. It’s not an easy craft, and challenging it alone is asking for sure failure.

2) Your career, just like everyone else’s, has had its ups and downs. How do you cope with the rollercoaster ride, specifically when the cart is not at the top of the hill?

Thanks for flattering me with calling what I have done a “career” but in all honesty, I have had a job in comedy all these years. I have appeared on a few TV shows, but like a baseball player who plays in the minors for twelve years and maybe gets a “cup of coffee” in the big leagues, my name is not on anyone’s “who’s who” list. I have practiced my craft for decades, and have been able to squeak out a living. Some years have been better than others, but it’s always a struggle to get that next run of bookings.

To make things more complicated, I got into morning radio years ago and have had many jobs all over North America. That’s a horrific business, and makes standup comedy look like a civil service job security-wise. That has added a lot more complexity to my personal journey, and I should have chosen one or the other. But I didn’t. I was looking for “security” and “stability” which just doesn’t exist in the entertainment business. It’s always a roller coaster ride, even with the top stars. Nothing lasts forever, and that can be a positive or negative depending on how one chooses to view it.

I was lucky enough to interview Kenny Rogers years ago and he couldn’t have been more insightful, encouraging, and down to Earth. He talked about how he would never allow himself to get really up or really down, because he knew the pendulum would swing the other way soon enough. He said when it was going well he’d enjoy it but did not get cocky because he knew it wouldn’t last. He said the same was true when it wasn’t going well, so he refused to let himself get down as he knew things would turn his way soon enough. I thought this was an outstanding way to think and I have tried to implement it in my own life. I think others would benefit from it as well.

3) You were also in radio for many years. How did it help and/or hurt your comedy career? Are you coming back on air anytime soon, besides your many guest appearances you still do?

OOPS, got ahead of you. 🙂

I did morning radio which is essentially the headliner of the radio station. The bulk of the money in promotion (which usually isn’t much) goes to the morning show, and it’s the one the sales force focuses on the most. The success of the morning show determines the success of the radio station, just as the headliner determines the success of a comedy show.

It helped my comedy pursuit in the cities where I worked. I would always do guest sets in whatever town I worked, and it helped get listeners for the radio show. It hurt in that it kept me local or at least regional, and I wasn’t able to spread out across the country like I would have liked.

Comedy and radio are very different skills, and I happen to be one who can do both well enough to get hired consistently. That’s not bragging or showing off, and there sure are a whole lot of things at which I am terrible, but for whatever reason standup comedy and radio are skills I was able to learn quickly and get hired.

Someone once described the difference as comedy is doing the same material to different audiences every night while radio is doing different material to the same audience every morning. I think that sums it up really well. Some can do one or the other, and I have seen all kinds of radio people who think they can do comedy and vice versa. They are both difficult skill sets to master, and it takes years to do both.

I love radio and have been doing some guest fill-ins for a sports talk radio station in Milwaukee. I also had a paranormal talk show for a while which was really popular until the station got sold and I got booted — a very common radio scenario. I am starting that up again as a video cast, and it’s really fun. It’s called “The Mothership Connection” and we have a channel that has our shows cataloged. We also have a Facebook page at

4) You have taught comedy and have over 2,000 people who have received the benefit of your teaching. I’m a member of your FB page “The Maxwell Method of Stand-up Comedy” and continue to learn things and connect with some great folks. Why did you start the page and is this another form of your teachings? Is this a book in the making?

Yes, I have taught classes for more than 2,000 students since 1993. I had a nasty car accident in 1993 in Milwaukee and was near death. I had no food and no gigs, and I was really scraping bottom. A local college contacted me and asked if I might be interested in teaching a comedy class. I politely said there was no way to teach comedy as one was either funny or they weren’t.

They responded “We’d be willing to pay you a few bucks.”

I responded “Tuesday at 7 we will have a comedy class!”

I had NO clue what I was going to “teach” anyone but I knew I had made more mistakes than I could count and knew what NOT to do. I went at it with the approach of if I was starting over again what did I wish I knew that I didn’t? I taught from that angle and it just kept growing. I love teaching, as it keeps me close to the fundamentals of comedy.

As far as the Facebook group goes, I’m in a transition right now. I have put all kinds of time and effort into it to try and educate new comedians, but there has been a steady group of newbies who think (wrongly) they know it all. I am taking a hiatus for a while and will either come back stronger or shut it down permanently. I’m not sure yet.

5) Speaking of books, you’re also a published author. Tell us about “Monkey in the Middle”.

All of us as entertainers have a private life, and before I was a comedian I had a childhood best friend as most of us do.

Mine happened to be head of security at a bank and he and his crew lost their jobs as the bank chose to hire another security company. My friend decided he wanted to get back at his bank manager and planned to rob the bank to “teach him a lesson.” Well, he had $105,000 of stolen bank money in the trunk of a rental car in my name as we took a cross-country trip from Milwaukee to Las Vegas. I had no idea the money was there until almost a year later. Needless to say I was more than a bit shocked to find out.

One thing led to another and eventually he decided to rob the same bank again. He wore a gorilla mask, tuxedo and carried helium balloons, hence the title “Monkey in the Middle.” He tried to blame that second robbery on me, and I had to wear a wire for the government to get him to confess. It took several years to play out, and there are a lot of stories both funny and dramatic that make the book a page turner.

People who have read it love it, and are passing it along to their friends. I get emails regularly that say, “I don’t know who you are, but my friend gave me your book. I can’t put it down!”

It’s available at my publisher’s website No worries if you don’t get a copy. There won’t be any quizzes. 🙂

6) You’ve also opened The Kenosha Comedy Club in southeast Wisconsin, what was that process like and what do you perceive moving forward with this new endeavor?

For those that don’t know, Kenosha is located between Chicago and Milwaukee and is becoming a boom town. They just built a HUGE Amazon warehouse and are building another one for a business called U-Line. The population is about 100,000 but people are moving up from Chicago at an alarming rate and it’s growing like crazy.

I did radio in Kenosha years ago, and have many friends here. I know a guy who owns a local magazine and told him we could probably do a weekend comedy room at some point. He found a hotel that was willing to do it and we started New Year’s Eve of 2017. It’s still pretty new but it’s been growing every week, and I am putting a lot of effort into building a brand. Our audiences are mostly 40-70 and like cleaner shows. I have been booking acts who fit into this category and audiences have been really positive about it.

I am a 1/3 owner along with the hotel owner and my magazine publisher friend. I am in charge of the comedy aspect, and that’s all I know. I wouldn’t know how to run a bar if my life depended on it, and of course that’s where the bulk of the revenue comes in. This is a joint venture, and we all need each other’s expertise. So far, so good!

7) Thanks again for doing this interview Dobie, any last thoughts or…warnings?!! (haha)

schlitz-caricature-1aBrian, thank YOU for having me. Like me, I know you’re a comedy “lifer” and want the craft to continue to future generations. Not everyone can do it but those of us who can know just how difficult it is to make one’s exclusive living at this. There are all kinds of unexpected pitfalls none of us ever expected, but become part of our daily existence.

If there’s one thing I would suggest to anyone starting out, it’s get to know the business side early. It’s Show BUSINESS, and it should be the other way around as that’s the most important aspect. Being funny is fine, but there are a lot of funny people. Being able to craft it into a business is something else entirely. There are ugly things to look after like taxes and creating products to sell, and so many other things we never thought we would have to deal with.

In essence, every comedian is self-employed and most of us never look at it that way — at least at the start. In reality that’s exactly what it is, and the sooner we learn to deal with the business side the more likely we are to be around longer than a year or two. It’s a LONG road, and there are lots of obstacles to overcome.

I sure wish someone would have told me that invaluable pearl of wisdom when I started, but I had to learn the hard way — and I still am. I made all kinds of mistakes that didn’t need to happen but did, only for the fact I was too shortsighted to see the bigger picture. Be smart and don’t do what I did. Treat this as a business first!

Whatever anyone does, I wish them all the best. Have fun and know it’s a hard road. That will hopefully keep you grounded in the bad times and humble in the good ones.

Best of luck to us all!

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Comedian Brian T Shirley has been in the Business for 20 + years. His act is derived from growing up poor, divorce, the USAF, partying, relationships, infomercial's, sports, and more. He has performed all over the U.S., Canada,The Bahamas and Japan. He also works Country Clubs and corporate events all over the U.S. He has done special engagements such as a tour of Japan to entertain the troops, opening for Huey Lewis and The News, The "Laughter for Love" benefit for Va. Tech, & a Country music festival for Dodge trucks. Brian has performed @ The Jokers Wild Comedy Club inside the Atlantis Resort on Paradise Island,The Bahamas & for Carnival Cruise Lines. Brian is also a philosopher.he's written 2 books of wisdom &wise sayings called "Make Love Not Warts", and "Four Score and Seven Beers Ago..." (Which recently won the "Amazing Book Cover Art Award" in a contest sponsored by LeRue Press) BRIAN"S THIRD BOOK , "A Funny Thing Happened on the Way to the Club" contains short stories about his life on the road as a professional comedian. Brian has created and hosts a WEB Series about being a stand-up comedian on the road called "BTS On The Raod" which can be seen on Youtube, American Hearts Radio WEB TV Network every Saturday @ 8 PM EST and in the online magazine No Strings Attached-E News. Brian's a weekly guest host on a segment called "BTS Entertainment Corner" on Janice Hermsen's radio program "What's The Story" every Friday @ 2:30 PM EST on Brian also co-hosts a monthly radio show on The Lina Jones Diamond Network called "The Lina and Brian Hour". Brian has done Voice over work for the award winning WEB Series "U.S.E." (2014) and the feature film "Inside Ben" (2016) and he's a main character in the animated feature "Professor Gravitron Saves The Universe" (2016).


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