J

eff Dwoskin of West Bloomfield is the host 
of Classic Conversations, a podcast show he 
created during the COVID pandemic to 
satisfy his insatiable appetite for pop culture, TV 
and movie stars, writers and comedians. It leans on a 
heavy dose of the good old days in show biz. It’s not 
his day job, just a side dream job, that now finds him 
in the top 1.5% of listened-to podcasts. 
In the “real” world, Dwoskin has spent more than 
30 years as an E-commerce, digital and social media 
maven, his talents traversing him through the tech 
and creative worlds in Detroit, including a stop 
at Little Caesars Pizza as its director of consumer 
engagement.
Today, he’s a partner in a company he co-founded 
with his wife, Robyn, called Stampede Social that 
has “created game-changing software to help inspire, 
manage and measure engagement on Instagram.
” It’s 
very fascinating, innovative, cutting-edge technology 
that is above my level of comprehension. 
However, there’s another side to Dwoskin that is 
smack-dab in the middle of my comfort zone. He’s 
also a writer, comedian and a lover of all things 
nostalgia. And, for the past four years, he has found a 
way to nurture those passions through his podcasts.
It’s a tremendous understatement to say Dwoskin’s 
guest list has come a long way since July 2020, when 
somehow he chose me for his ninth podcast subject. 
He won’t admit it, but I still believe I was a test case. 
Dwoskin has raised the talent bar since and has 
grown exponentially as he learned the ropes of 
being a first-time, self-taught interviewer. The first 
conversations were brief and lasted only 15 minutes 
and involved very little prep. 
Today, he has honed his skills and amassed more 
than 300 interviews, many featuring stars from some 
of television’s most successful and iconic sitcoms, 
each lasting between 45 minutes to an hour. 
Among them include Ed Asner of The Mary 
Tyler Moore Show and Loretta “Hot Lips Houlihan” 
Swit from MASH. Plus, cast members from Happy 
Days, including Donny Most (Ralph Malph), Anson 

Williams (Potsie) and actress Marion Ross, yep — 
Richie’s lovable mom, Mrs. Cunningham herself! Or 
as the “The Fonz” would say: “Mrs. C — ayyyy!” But 
wait, there’s more!
The lineup of Classic Conversations is like flipping 
through a TV Guide magazine of yesteryear, also 
featuring lead actors from The Love Boat, Lassie, 
The Brady Bunch, Little House on the Prairie, The 
Munsters, Batman, The Danny Thomas Show — and 
more classic shows than you can shake an old metal 
TV antenna at.
There’s plenty more podcasting pontificating about 
Jeff still to come including his conversations with 
notable Jewish entertainers. But first, a fun backstory.

COMEDY CONNECTION
Jeff Dwoskin and I first crossed paths in 2007 when 
the Dick Purtan Morning Radio Show on WOMC 
created the “Purtan Protege Contest.
” It was a talent 
contest looking for the funniest folks in Detroit. 
Fledgling comedians from our listening audience 
flooded us with auditions on cassette tapes and CDs, 
and Jeff was among them.
We narrowed down the field to a few finalists. The 
payoff was a chance for them to appear as an opening 
act for the Dick Purtan Comedy Night Out! on July 
13, 2007, at the Royal Music Theater. The evening 
benefited the Gail Purtan Ovarian Cancer Research 
Fund.
That night, our comedic contenders vied for the 
title of Purtan Protege with their fate in the hands 
of Purtan’s People judges. It was a big deal, with big-
time national headliners on the bill.
Making a rare, special return to do standup was 
(drum roll) Michigan’s one and only Tim Allen! 
Tim has known Dick Purtan for years and has 
generously donated to many of his charitable causes. 
His agreeing to appear in person before a sold-
out audience in honor of the radio icon took his 
generosity to a whole new level. 
The night also featured popular national standup 

‘Classic 
 Conversations’

ALAN MUSKOVITZ CONTRIBUTING WRITER

OCTOBER 31 • 2024 | 49
J
N

Jeff Dwoskin’s podcast show will satiate 
your hunger for pop culture and nostalgia.

continued on page 50

Dwoskin doing his standup comedy

Jeff Dwoskin and Dick 
Purtan at the Comedy 
Night Out event

DAN LIPPITT

