I couldn’t wait to talk with comedian Steve Dupin.
I hate to even type his name that way.
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He’s the likable, hair-flipping, Trans Am-loving, fiercely American “Stevie D” to those who watch him perform.
I’ve seen his act a couple of times in Nashville.
Both times I laughed until my face hurt.
I definitely have a feel for Stevie D the comedian.
He’s ALWAYS worth the price of admission.
But as usual, I want to find out who people are when they’re not on stage and figure out what makes them tick.
When I interviewed him just before the Fourth of July weekend for 4th Door Media, I introduced him as a comedian, author, cancer survivor, husband, father, and—most importantly, perhaps—a Trans Am owner.
I asked him if I was missing anything.
His answer?
“You should start with the Trans Am. That’s the lead. That’s my identity... that and the hair flip.”
Fair enough.
Check out his social media and you’ll see him driving or standing proudly beside his beloved Trans Am (or his “Kentucky Porsh,” as the license plate says below).
He says his obsession with the Trans Am began as a kid watching Smokey and the Bandit with his dad.
“Ever since that scene where the Trans Am rolls off the back of the 18-wheeler... boom. I was like, ‘That’s my jam.’”
Even after moving to California, he proudly called himself:
“The Hollywood Hillbilly with the Trans Am.”
He says he’s a “T-tops-off and 8-track-rockin’” kind of guy.
As for his style and his comedy, Stevie D says:
“Either you get it or you don’t. You’re my people or you’re not my people.”
That’s Stevie D in one sentence.
Ten pounds of authenticity in a five-pound bag.
There Was Never a Plan B
A lot of people dream about Hollywood.
Very few actually leave home with no safety net.
Stevie D did.
Growing up in Kentucky, factory work was simply what everyone around him did.
In fact, his mom worked in one for 45 years.
But Stevie D couldn’t stop watching television.
Even as a kid, he watched shows with a childhood curiosity about how they were made.
He discovered The Dick Van Dyke Show and became fascinated with writers.
He watched Dick Clark getting paid to talk about music and thought:
“That’s all I wanted to do... talk about music, be funny, cause trouble and do hair flips.”
Weeks after high school graduation, he did what a lot of teenagers dream of doing but rarely act on.
Instead of attending Western Kentucky University, he drove straight to Panama City Beach!
I’m wondering why on earth I never thought about doing that.
Anyway, he became a DJ at the famous (to spring break types) Spinnaker Beach Club.
It’s the same place he visited as a high school junior over spring break.
Afterwards, he went back to school telling anyone who would listen that one day he'd move there and become a DJ at that very club.
He says, “And that’s what happened. Too bad I didn’t visit the White House!”
Then Stevie headed west with no connections, no backup plan, and little money—but a whole lot of belief.
“I’d never been to California. No Plan B.”
You hear stories about people who do that, but you rarely meet someone who actually has the guts to go for it.
“You just have to believe in yourself. It doesn’t have to be, ‘I’m going to be famous.’ It can be all about doing what I love to do.”
A Throwback Who Sees the Positive in Difficult Situations
What was it like for young Stevie D growing up?
“We didn’t have air conditioning. We didn’t have a car. We were on food stamps. I had a single mom... but we were happy.”
He says he didn’t waste a whole lot of time focusing on what his family lacked.
Instead, he remembers BMX bikes.
Jumping trash cans.
Raising hell.
Being a kid.
“It doesn’t take a lot to make me happy.”
That philosophy still holds true today.
He says he starts every day thinking about what he’s grateful for.
“I’ve got a beautiful family. I’m grateful. I’ve got a Trans Am. I can tell jokes. Sometimes I get paid.”
That may be the most Stevie D sentence ever spoken.
The California Girl Who Balanced the Hollywood Hillbilly
You’ve heard the saying:
“Behind every successful man is a strong woman.”
For Stevie D, that’s his wife, Katie.
They met at the legendary Comedy Store on the Sunset Strip.
She worked in an upscale Beverly Hills art gallery.
He walked in carrying what he believed was priceless artwork.
As it turns out...
Not so much.
“It was a terrible folk art picture of Elvis looking at a cross in the sky with a tear coming out of his eye.”
He proudly paid $25.
Katie politely told him...
“The frame may be worth $25.”
Twenty-six years later, they’re still laughing, still living, and taking nothing for granted.
But as much as the California girl loved her roots, the beautiful beaches, and everything Southern California had to offer, it was no longer the right fit for the Dupin family.
Like many others, they traded California for a simpler life.
Katie followed her Hollywood Hillbilly to Hendersonville, Tennessee.
Turns out...
She loves it.
It’s home now.
Comedy Isn’t About Talking
I asked Stevie D where he finds inspiration for his jokes.
The answer?
“I’m observational.”
He basically observes everything everywhere he goes.
He believes great comedians say the things audiences are already thinking.
“A good comic should say something out loud that you’re thinking.”
Even failed jokes, he says, aren’t failures.
They’re workshops.
“When that happens... you’ve got to address it.”
People don’t necessarily care when a joke bombs, he says, but they will notice how you handle it.
Cancer Changed the Story... Not the Man
In his early 40s, Stevie D was diagnosed with prostate cancer after an earlier doctor failed to order routine bloodwork.
Time to get serious, right?
He decided to write...
Wait for it...
...a funny cancer book.
“My twisted mind said, ‘I’ve got cancer... now I can write a funny cancer book.’”
Only Stevie D could say that.
He’s quick to point out there’s nothing funny about cancer, and he applauds everyone who has had to heroically deal with the disease in one way or another.
His book, The Trans Am Diaries, became an Amazon bestseller.
Then life rewarded him with one of those moments you simply can’t script.
Remember when I said he had originally planned to attend Western Kentucky University but bolted to sunny Florida instead?
Well, his very first book signing took place...
You guessed it...
...at Western Kentucky University.
“Bro... I’m a little late for class,” he deadpanned.
Hope
More than anything else, one word kept coming up during our conversation.
Hope.
You may have noticed I write a lot about what it takes to be “unbreakable” in this wild and wacky world we live in.
When I asked Stevie what being “Unbreakable” meant to him, his answer was no joke.
“As long as you have hope and faith... it’s all good. If you lose hope... that’s when it gets dark.”
That’s coming from a man who has battled cancer, built a career in one of the toughest industries in the world, raised a family, reinvented himself time and time again, moved across the country, and still, somehow through it all, remains relentlessly positive, grounded, and grateful.
The Dream Isn’t the Destination
We all chase dreams.
Not all of us achieve them.
But dreams change.
Circumstances change.
Priorities shift.
So what do you do?
“You pivot,” he says.
And that’s okay.
Because, as Stevie says:
“Happiness is the journey. The dream is the journey—not the destination.”
As we wrapped up our conversation, he shared one final thought that I’m going to steal and try to focus on from the moment I wake up tomorrow morning.
“Open your eyes with gratitude. What are you grateful for?”
Not bad, Stevie D.
Not bad at all.
Just so you know...
This Hollywood Hillbilly is grateful for a whole bunch.
His career.
Family.
Faith.
Hope.
A Trans Am.
And without a doubt...
One more hair flip that will no doubt make someone, somewhere, laugh out loud.
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