Journey in Some Amazing Moccasins

March 2018

It was a cold afternoon in February when I sat down for coffee with Leonard Dick, accidental comedian, motivational speaker, and retired playboy.

“Retired?” I ask skeptically. I don’t believe it for a second.

“You better believe it,” says Leonard with a grin. “I’d be in big trouble. My wife writes all my material!”
With his alter ego of Moccasin Joe, Leonard has been an icon of the northern comedy scene for over 30 years. He is also a sought-after motivational speaker and workshop leader, with a unique way of fusing humour into some dark situations.

“Comedians go through the school of hard knocks,” he says. “You see the funny in everything. But there’s a point in life when you’re a public figure that you have a responsibility. You have to give back.”

And Leonard certainly does. His personal blend of real-life comedy soon transitioned into workshops and speaking engagement that have taken him all across North America, bringing laughter and healing to big cities and small communities alike. He finds humour in every day situations and I realize that perhaps his greatest gift is his relatability, for his life wasn’t always sunny and bright.

“I lived on streets all over Canada for 5 years,” says Dick. “I was kicked out of my community because of alcohol and drugs. It’s a dark world and I was in a dark place. Imagine how good it felt to go back to that community years later as a motivational speaker. It felt good. Really good.”

Leonard’s journey to emotional health was a long one, and he admits that two people were instrumental on his road to sobriety and strength.

“Forty-four years ago, when I was living on the streets, I met an old Jewish gentleman. At least, I think he was Jewish because he wore a yamaka (or yarmulke) on his head. On some days, he used to come with bread and cheese. On others, he’d come with socks and underwear. I never did know his name, but he gave me my first sense of pride and self worth. So I did the hokey pokey and turned myself around.”

From there, Dick began to apply his formidable personality to changing lives, beginning first with himself. He graduated from the Ontario Police College in Brampton, ON, immediately finding work with Correctional Services, and later as a customs officer at the Can/US border.

“I was a correctional officer and a damn good one,” says Dick. “The men would always thank me for sharing my story, or say that they’re sober to this day because of me. I saw myself in them. I’ve always tried to give people the benefit of doubt. You don’t know how far a smile can go in someone’s life.”

The second person he credits for his continued success is his wife Ann.

“I was working hard and bringing up two sons on my own until she came along,” says Dick with a smile. “She stepped in, stepped up, and became a full time mom. When we first started out, we didn’t have a nickel, but we made do and we made fried bread. She is beautiful and likes to laugh. My family has been blessed with strong, positive women.”

Leonard and Ann now have four grown children, Michael, Dion, Christina, and Darcy, along with ‘so many grandchildren’ that he’s lost count. I know he’s joking, because he’s very proud of them all.“I love spending time with them, singing songs about fried bread!”

Leonard has always been funny, but his first experience in stand-up comedy came through an unusual, almost accidental, route. He and Ann are artists and entrepreneurs, selling arts at craft shows throughout the region, where he became known as the go-to guy for a good story or a laugh.

“I always had a joke,” says Dick and he shrugs. “It was good for business.”

One day, they were selling crafts at a conference and he heard that there was a new speaker taking the stage. He was curious, so went to inquire about tickets and found out that the speaker’s name was Moccasin Joe (his nickname from his son Michael). Leonard was in shock, but he was up for the challenge and took the stage, telling funny stories about his life. To his surprise, people loved it. His stories came from real life, the hardships and the joys and the ability to find humour in all situations. That was the start of a long and varied career, taking him from the Comedy Club at the Landmark Inn to the World Indigenous Peoples Conference.

“There was supposed to be 200 people,” says Dick. “But 700 signed up. I was terrified but figured it out thanks to Ann, who does a lot of writing for me. Travelling in my comedy act, I’d see people struggling with various painful issues, but I know laughter combats stress and depression. It brings a positive energy to dark places.”
Dick has made a career bringing his trademark sense of humour to workshops and conferences all over the world. From Alaska to Arizona, from Labrador to British Columbia, he has discovered that, while cultures may differ, laughter is the common language between them. Well, laughter and food.

“There was one year I had 17 turkey dinners!” he laughs. “I get fed everywhere I go! First seal meat in St. Paul Island; crab in Dutch Harbor! Don’t get me started on the fried bread!”

Our conversation grows serious now as I ask Leonard where he thought life might take him now that he’s ‘retired.’

“I never dreamed that I’d ever have this opportunity to be this Moccasin Joe,” he says, wistfully. “Not everyone likes it, but for the ones that do, they love it. I never want to offend, but I need to speak my truth. I want to finish another book, maybe go into Indian Affairs. I hear a lot of things. I see a lot of things. I’ll never stop wanting to help people.”

I also ask him what advice he might have for folks struggling through tough times in their lives.

“The sun goes down but the sun always comes up,” he says with tears in his eyes. “You may not always have what you want, but you have you. You are powerful enough to overcome if you focus on happiness, humour, and a sense of giving. Ask the creator and expect an answer. There are a lot of negative things, but there are also a lot of positive. Listen to your creator with thanks and pay it forward. It’s not an easy way. Every day is complicated, but you can overcome. Live, really live, until you die.” And he grins again. “It’s okay to be crazy.”

For more on Northwestern Ontario’s most positive comedian, check out Facebook at or his website at

Heather L. Dickson is a photoshop guru, zoologist and author of 6 novels.

Visit her website at

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