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Classic Conversations

Take a deep dive into pop nostalgia with us! Pop culture influencers, TV stars, film actors, comedians, and musicians share inspirational stories about the road to success. Insightful conversations that are part comedy/part drama and are always entertaining! With your host, comedian, Jeff Dwoskin.
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Latest Episodes

Rich Little: A Thousand Voices and the Stories Behind Them

May 25, 2026

Rich Little has done impressions of presidents, Rat Pack legends, and Hollywood royalty for decades, but the stories behind those performances are even more entertaining than the impressions themselves.

The man of a thousand voices sits down to share what it was really like performing in front of the very people he was imitating, the moments that went sideways, and what keeps him performing in Las Vegas to this day.

Show Highlights:

  • What happened when Frank Sinatra quietly appeared onstage while Rich was in the middle of doing Frank Sinatra.
  • The very specific coaching George Burns and Jack Benny each gave Rich on how to imitate them better.
  • Why Rich Little finished an entire episode of The Muppet Show with a rash on his face.
  • The moment at the Dean Martin Roasts when Rich tried to teach Jimmy Stewart how to do his own impression.
  • How Rich Little's swearing-in as a US citizen left him genuinely unsure who had just become an American.

You're going to love my conversation with Rich Little

Follow Jeff Dwoskin (host):

Ways to support the show: SPONSOR: STAMPEDE SOCIAL Drive engagement from your social channels and podcast with Stampede Social's Instagram and Facebook DM automation! Visit https://stampede.social Also check out: Why Instagram + Stampede Social Is the Growth Strategy Podcasters Need in 2025 (and Beyond)

Thanks for checking out Classic Conversations! Dive into pop culture nostalgia with comedian Jeff Dwoskin as he hosts the best TV and film interviews. Hear inspiring stories from actors, comedians, musicians, and pop culture icons about the road to success. Part comedy, part drama—always entertaining.


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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The $2.5 Billion Queen of Pitch Dr. Forbes Riley Reveals Her Secrets

May 18, 2026

From a gapped-tooth kid who dreamed of Hollywood to the woman who gave Kim Kardashian her first TV appearance and generated over a million dollars a day on home shopping, Dr. Forbes Riley has built one of the most extraordinary careers in entertainment and sales history.

In this conversation, Forbes opens up about the acting career that took her from Splatter University to Broadway opposite Christopher Reeve, the pitching philosophy that turned her into a $2.5 billion force in infomercial history, and why her brand new book, Pitch Secrets A to Z, is really a life skills manual disguised as a business book.

Show Highlights:

  • The story behind how Forbes invented her own talent agency, complete with a fictional British manager named Lindsay Maxwell, and booked herself into Broadway, commercials, and movies before anyone found out.
  • Forbes was the woman in the room when Kim Kardashian filmed her very first television appearance, and she shares what she remembers about that day.
  • She played Lily Tomlin's iconic one-woman show for six months straight, learning every one of 250 pages through hypnotherapy after nearly quitting the production.
  • Forbes breaks down a live pitch in real time, getting a yes out of thin air using just a question and an embedded command.
  • Her philosophy that pitching is not selling but enrolling, and why the people who find it pushy are usually the ones who need it most.

You're going to love my conversation with Forbes Riley

Follow Jeff Dwoskin (host):

Ways to support the show: SPONSOR: STAMPEDE SOCIAL Drive engagement from your social channels and podcast with Stampede Social's Instagram and Facebook DM automation! Visit https://stampede.social Also check out: Why Instagram + Stampede Social Is the Growth Strategy Podcasters Need in 2025 (and Beyond)

Thanks for checking out Classic Conversations! Dive into pop culture nostalgia with comedian Jeff Dwoskin as he hosts the best TV and film interviews. Hear inspiring stories from actors, comedians, musicians, and pop culture icons about the road to success. Part comedy, part drama—always entertaining.


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Open Audio Episode Page

Golden Girls, Laverne & Shirley, Gary Shandling and the Stories Nobody Tells

May 11, 2026

Marc Sotkin has written and produced some of the most beloved sitcoms in television history, and the stories behind those shows are even better than the episodes themselves.

From selling underwear in Houston to running the writers room on Golden Girls, Sotkin's career is a masterclass in persistence, instinct, and surviving chaos with a sense of humor.

Show Highlights:

  • How an underwear salesman from Texas talked his wife into moving to Hollywood and somehow made it work.
  • The $15 quiz show question that was rewritten before it ever aired, and why it still bothers him.
  • The secret comedy duo Marc Sotkin formed with a young Gary Shandling before either of them were famous.
  • The Laverne & Shirley season that included a star quitting, a cast member dying the night before a shoot, and Jim Belushi saving the day.
  • Why the showrunner of Golden Girls eventually ran the show from Boulder, Colorado, flying in twice a week.

You're going to love my conversation with Marc Sotkin

Follow Jeff Dwoskin (host): Ways to support the show: SPONSOR: STAMPEDE SOCIAL Drive engagement from your social channels and podcast with Stampede Social's Instagram and Facebook DM automation! Visit https://stampede.social Also check out: Why Instagram + Stampede Social Is the Growth Strategy Podcasters Need in 2025 (and Beyond)

Thanks for checking out Classic Conversations! Dive into pop culture nostalgia with comedian Jeff Dwoskin as he hosts the best TV and film interviews. Hear inspiring stories from actors, comedians, musicians, and pop culture icons about the road to success. Part comedy, part drama—always entertaining.

 


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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Greg Evigan on BJ and the Bear, My Two Dads, TekWar, and a New Album

May 4, 2026

Greg Evigan has lived one of the most colorful careers in Hollywood, and this conversation brings all of it rushing back.

From the stages of Broadway to the cab of a big rig, from a home recording studio he built himself to Abbey Road in London, Greg sits down to revisit the stories, the shows, and the music that have defined his remarkable life. Along the way, he reveals that he has never stopped chasing the thing that started it all: the music.

Show Highlights:

  • Greg wrote the iconic My Two Dads theme song in just 20 minutes with writing partner Lenny Macaluso, then had to play it for producer Michael Jacobs on a cassette tape in a car 15 times before getting the greenlight.
  • BJ and the Bear pulled a staggering 47 share on its premiere night, meaning nearly half the country was watching. NBC executive Fred Silverman had tried to kill the show by scheduling it against the movie Network, and it crushed the competition anyway.
  • Greg turned down the lead role in Knight Rider, and he has no regrets. As he puts it, after years of talking to a chimp, he was not about to start talking to a car.
  • The new album, Greg Evigan with London's Royal Philharmonic Orchestra, features 8 original pieces Greg wrote and performs on piano, recorded with a 65-piece orchestra at the legendary Abbey Road Studios in London.
  • Greg shares a jaw-dropping story from the Grease memoir book about a well-connected New Jersey "relative" who offered to handle a casting problem the old-fashioned way, involving Jeff Conaway's knees. Greg politely declined.

You're going to love my conversation with Greg Evigan

Follow Jeff Dwoskin (host): Ways to support the show: SPONSOR: STAMPEDE SOCIAL Drive engagement from your social channels and podcast with Stampede Social's Instagram and Facebook DM automation! Visit https://stampede.social Also check out: Why Instagram + Stampede Social Is the Growth Strategy Podcasters Need in 2025 (and Beyond)

Thanks for checking out Classic Conversations! Dive into pop culture nostalgia with comedian Jeff Dwoskin as he hosts the best TV and film interviews. Hear inspiring stories from actors, comedians, musicians, and pop culture icons about the road to success. Part comedy, part drama—always entertaining.

 


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Open Audio Episode Page

How Gossip Girl Defined a Generation of TV Fans with Lindsay Denninger

April 27, 2026

A deep dive with Lindsay Denninger into the cultural phenomenon of Gossip Girl reveals just how powerful storytelling can shape generations.

From downloading episodes overseas to becoming fully immersed in the fashion, music, and drama, Lindsay Denninger shares how Gossip Girl became more than just a show, it became a defining force in pop culture. Through her new book, she explores the lasting influence of the series, from its groundbreaking pilot to its commentary on fame, identity, and the rise of digital surveillance. This conversation unpacks the nostalgia of early 2000s television while examining why certain storylines still resonate—and others don’t. It’s a candid look at fandom, storytelling, and the messy brilliance of iconic TV.

Show Highlights:

  • The unexpected rise of Gossip Girl during the 2007 writers strike
  • How teen dramas shaped identity and pop culture in the 2000s
  • The behind-the-scenes reality of writing about television and celebrities
  • Why the show’s themes feel more relevant today than ever
  • A critical look at controversial storylines and character arcs

You're going to love my conversation with Lindsay Denninger

Follow Jeff Dwoskin (host): Ways to support the show: SPONSOR: STAMPEDE SOCIAL Drive engagement from your social channels and podcast with Stampede Social's Instagram and Facebook DM automation! Visit https://stampede.social Also check out: Why Instagram + Stampede Social Is the Growth Strategy Podcasters Need in 2025 (and Beyond)

Thanks for checking out Classic Conversations! Dive into pop culture nostalgia with comedian Jeff Dwoskin as he hosts the best TV and film interviews. Hear inspiring stories from actors, comedians, musicians, and pop culture icons about the road to success. Part comedy, part drama—always entertaining.


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Open Audio Episode Page