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comedian Kathleen Madigan, on her own, no stranger 
to sold-out audiences when visiting Detroit.

AND THE WINNER IS ...
Despite the pressure of appearing before the likes of 
Allen and Madigan, our Purtan Protege finalists were 
more than up to the task. To a person, their material 
rocked. It was a very difficult decision for the judges, 
but the choice was unanimous. Jeff Dwoskin was 
crowned Purtan Protege!
Jeff was simply brilliant that night. “Tim Allen’s 
mom came up to me afterwards to tell me how much 
she liked my set,
” Jeff said. “The ultimate compliment.
”
Dwoskin walked away with a trip to Mexico and a 
lifetime of memories, including some pre-show quality 
time with Allen of Home Improvement and Last Man 
Standing TV fame. Yep, Jeff was in the company of 
a talent responsible for nearly 20 years of top-rated 
television sitcom history. Yet Dwoskin’s pinch-me 
moment would come later. 
“I remember hanging out with Tim Allen back-
stage,
” Dwoskin said. “But it wasn’t until the next day 
I remembered kicking myself because I had blanked 
out on the fact that I had been talking to fricking Buzz 
Lightyear from Toy Story!” 
Winning the Purtan Protege contest was not 
Dwoskin’s first standup comedy rodeo. He had 
appeared at some smaller local comedy clubs. But by 
winning the Purtan contest, he eventually joked his 
way up the comedic ladder and found himself headlin-

ing at the legendary epicenter of Detroit comedy stops 
— Mark Ridley’s Comedy Castle in Royal Oak.
Yes, Dwoskin’s comedy chops were getting noticed, 
but at the end of the day, the gigs were never intended 
to replace his passion for and work in the ever-chang-
ing high-tech world, where he remains to this day — 
except when he slips away to produce another enter-
taining podcast.

THE PODCAST PROCESS
To secure many of his interviews, Dwoskin reaches 
out to agents, publicity representatives and a variety of 
networking connections he’s made over the years by 
attending Comic-Cons, conventions where pop culture 
and nerds collide.
The multi-day events around the country draw writ-
ers, actors and directors who meet and speak to thou-
sands of adoring fans, many who dress up in costumes 
of their favorite characters. Jeff has been selected to 
lead many of those celebrity panels.
I haven’t gotten through all 300-plus of Dwoskin’s 
podcasts, but from what I’ve heard so far, the show’s 
name lives up to its billing. They are truly conversa-
tions, very personal in every sense of the word. They 
are simply not your run-of-the-mill, cookie-cutter 
celebrity interviews chocked full of predictable, cliche 
questions.
Dwoskin’s low-key personality and deadpan sense of 
humor (he never tries to out funny his comedic guests) 
creates a relaxed atmosphere that ultimately leads to 

his celebrity conversation subjects feeling more at ease 
to share behind the scenes details about their career 
journeys.
Equally key to Dwoskin’s success is the exhaustive 
preparation he puts into each and every podcast, 
something that is not lost on his guests. 
“I take a detailed, maybe obsessive approach to pre-
paring to speak to my guests,
” Dwoskin said. “I read all 
I can about them and listen to other interviews they’ve 
done because it’s important to know how much they 
talk when being interviewed. It gives me an indication 
of how hard I need to work to perhaps guide the con-
versation. Are they long answerers or short answerers, 
for example.
”
Dwoskin is not married to a prepared list of ques-
tions. He likes to keep it more improvisational. “I can 
have pages of notes, and I highlight pieces of them and 
have them scattered in front of me, but the only thing 
I know that I’m going to say is the intro,
” he said. “I 
always write that out because you can’t mess that up. 
But after that, the conversations take on a life of their 
own.
”
Those intros, by the way, often include something 
obscure Jeff throws in about his guests that really get 
their attention, his way of telling them, hey, this guy 
has done his homework and then some.
And that’s precisely why Classic Conversations are 
not your ordinary host/guest back-and-forth, rath-
er they end up sounding like heartwarming chats 
between two good friends. 

OUR COMMUNITY

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