An Examined Life with Jeff Allen 51: Laughing All the Way with Dobie Maxwell

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Dobie Maxwell (aka Mr. Lucky) is one of my favorite comedians from one of my favorite cities, Chicago. Not only is Dobie incredibly funny, but he has a heart of gold.

For instance, a dog in Kentucky, who just had a litter of puppies, was shot in the head and left for dead. Amazingly, she survived and was nursed back to health at an animal shelter. Then, somehow, she was shipped up to Wisconsin. Now, Dobie has had some runs of bad luck in his life, so he does charity events whenever he can as a way to help lift up people who are where he once was in life. So, while he was backstage at a charity event for the Wisconsin animal shelter, he met one of the people who worked at the shelter and invited her to bring the dog to his radio show the next day. And the dog took over the show! When a dog takes over a radio show, you’ve got one incredibly charismatic canine!

What Dobie didn’t know was that this morning with the survivor dog would lead to an opportunity with the NSA… no, not the ones listening to our phone calls, but the National Speakers Association (Where Professionals Speakers Connect). Dobie’s story of how a father’s influence on a man can alter is course in life is incredibly impactful… plus he makes everyone laugh while hitting at the heart.

As a guy once told me in regards to relaying a convicting message along with my comedy set, “If you can make a group of people laugh for 45 minutes straight, you’ve earned the right to take 15 and share whatever you want – especially if it will benefit their life and touch their soul.” And I think that’s where too many speakers go wrong – they focus too much on their message and neglect any humor in their delivery.

In fact, back in September of 2001, I was working at a comedy club in Las Vegas the day that the Twin Towers came down. I went to the club owner that afternoon and asked what he wanted to do, and he insisted that I go out there and tell jokes, then tell more jokes. Make them laugh non-stop and never ever mention the terrorist attacks. (Only in Vegas, right?) That very night, I called my wife and told her I needed to find another place or another way to work. I needed something with more significance and meaning, so I asked my manager if speaking at churches made any sense… or any money. Since then, I’ve found that speaking to Christian audiences is a good fit for me. So, my hope is that this new opportunity with the NSA is as good of a fit for my buddy, Dobie.

I’ve found that the toughest part of this whole “show business” thing is the business side of it. Guys like Dobie and me have figured out how to put on a show and make people laugh but the business part of the equation is something that a lot of us don’t get right.

As Dobie puts it, it’s like being left-handed or right-handed. Very few people are truly ambidextrous and aptly skilled with either hand. Likewise, guys like us might be very skilled on one hand (telling jokes); but clumsy as all heck with the other (business). Finding the next job, getting to the next town, nailing down the right deal… this is all like speaking a foreign language while using our opposite hand to write everything down for most entertainers.

Not to mention the complexities of having a family while working in show business. Not a day goes by when I’m not extremely grateful that I married a woman who was willing to stick around. There was a point where she wasn’t going to – having me on the road 40 weeks out of the year took its toll and she didn’t realize what she was getting into when she said “I do”. So, after some tough discussions, I said, “Well, we can cut our lifestyle in half and I can cut my travel down to only 20 weeks away,” which seemed workable.

But, before I knew it, I was applying for a job at Dominoes Pizza. I had been a stand-up comic for sixteen years, but I had the idea of learning to deliver pizzas and maybe someday own my own Dominoes franchise. Now, I had no skills other than telling jokes. (This is how idiots think)

So, in my head, I’m thinking I’m doing Dominoes a favor by bringing ME to the table! I was going to allow them to have ME deliver pizzas for them. Before I knew it, I had some 19-year-old with acne looking over my application.

“What do you do?”, he asked.

“I’m a comedian.”

“What’s that?”

“I tell jokes at nightclubs.”

“How does that qualify you for this job?”

I replied, “I’m applying to drive pizzas around town. You’re not splitting atoms back there, are you?”

So, apparently my interviewing skills had suffered, but I couldn’t believe that they thought I was unqualified to deliver pizzas! I said, “Look, I regularly find addresses of clubs in towns all around the country that I don’t live in. I can find addresses… that’s gotta count toward something.”

On my way home from my failed interview, I realized this was God humbling me to the point where I realized that He wanted me to go all-in with comedy and follow the doors He would open.

For years, I kept one eye on the lookout for some other way to make an easier living. I knew I wouldn’t last performing at comedy clubs. My wife was wanting to leave me, the money was going down, I was on a track to lose everything. But, every time I got to a point where I wanted to quit and I’d start looking for other lines of work, doors would slam shut and I’d get humiliated. It took a lot of humiliation for me to get the point that God had gifted me in a certain way and wanted to use those gifts for His work.

Image: Jason Merritt

Image: Jason Merritt

Dobie can relate. That’s largely why he went to radio… to find something different. He actually uses a swear word when it comes to what he was in search of: STABILITY. But, he quickly learned the instability of radio. It actually makes stand up comedy look stable. He’s been fired five times in all four U.S. time zones. As Dobie puts it, he was driving a Geo Metro, shoved all his worldly possessions inside of it and still had room to pick up hitchhikers. Life was not looking up for “Mr. Lucky”.

I remember doing a morning radio show in Iowa somewhere, and a month later I was sitting across the desk in another state, talking to the same DJ.

“Weren’t you just in Iowa?”, I asked.

“Yeah… I got fired, so I moved down here. That’s just the way the radio business goes.”

Talk about a career path that takes its toll on families! Radio wives simply get tired of moving. Even as a comic, we moved five times during my sons’ childhoods. It’s only by the grace of God that we all still love and like each other!

Yet, Dobie seems to have found a safer way to branch out… book writing! His life story, Monkey in the Middle, is available from Eckhartz Press.

Image: Eckhartz Press

Image: Eckhartz Press

“Born in Milwaukee to a biker father and drug abusing mother, Monkey in the Middle tells Dobie’s amazing story. When he was only five months old, his mother abandoned him and his two older siblings. Dobie was separated from his siblings and sent to be raised by his paternal grandparents. It was there, in his grandparents’ neighborhood, that Dobie befriended another societal misfit. The two became best friends.

Years later, as Dobie pursued his dream as a professional comedian and radio personality, that same “friend” robbed a local bank. He used Dobie as his unknowing getaway driver as they took a cross-country trip to Las Vegas in a rental car in Dobie’s name. The same friend robbed the same bank again two years later. This time he did it disguised as a Gorilla Gram–a robbery so audacious it made all the local television news programs. Who would have done such a thing? Law enforcement thought it just might be the work of a comedian, and all trails led to Dobie.

Dobie was dragged into the story against his will, and eventually had to make the excruciating choice of either testifying against his life-long friend in court or going to prison for crimes he did not commit.

Monkey in the Middle is hilarious, tragic, joyous, dark, and smart. In short, it’s just like the real life narrator of the story; Dobie Maxwell himself.” (Eckhartz Press)

The hard truth is that 99% of books that get published never sell 1,000 copies. But, serial killers and bank robbers always sell books. Dobie’s story has a bank robber, so the future looks bright!

Dobie is also working on helping other comics learn the ins and outs of the business through The Maxwell Method of Standup Comedy. As Dobie says, he’s made every mistake that there is to make, so he wants to help others by telling them what not to do… just like Colonel Sanders. The Colonel didn’t invent fried chicken, but he was the one to put his face on the bucket! Likewise, Dobie didn’t invent comedy, but he’s putting his name and his face on the Comedy Method Group. It’s a safe and encouraging environment for people of all ages and stages to learn – from up and coming comics to pastors and corporate speakers.

Like I said, things continue to look up for Dobie in all his endeavors. You can check out more of his work at

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