Classic Conversations: Pop culture Interviews with Jeff Dwoskin

Jeff Dwoskin
  • 4.9 (107)
  • Film History
  • Updated Weekly

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! If you love classic TV, if you love the movies, if you love film and tv interviews (see where I'm going with this), you'll love Classic Conversations with your host, comedian, Jeff Dwoskin.

  1. Rich Little: A Thousand Voices and the Stories Behind Them

    5d ago

    Rich Little: A Thousand Voices and the Stories Behind Them

    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 Facebook IMDB Richlittlevegas.com Rich's autobiography: People I've Known and Been Follow Jeff Dwoskin (host): Jeff Dwoskin on Twitter The Jeff Dwoskin Show podcast on Twitter Podcast website Podcast on Instagram Subscribe to my Youtube channel Yes, the show used to be called Live from Detroit: The Jeff Dwoskin Show Ways to support the show: Buy me a coffee (support the show) Dashery/TeePublic Store: Classic Conversations merch and more! Love the books I talk about on the show? Here is my Amazon store to shop. 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.

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

    May 18

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

    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 IMDB Instagram ForbesRiley.com Pitch Secrets A to Z by Dr. Forbes Riley Follow Jeff Dwoskin (host): Jeff Dwoskin on Twitter The Jeff Dwoskin Show podcast on Twitter Podcast website Podcast on Instagram Subscribe to my Youtube channel Yes, the show used to be called Live from Detroit: The Jeff Dwoskin Show Ways to support the show: Buy me a coffee (support the show) Dashery/TeePublic Store: Classic Conversations merch and more! Love the books I talk about on the show? Here is my Amazon store to shop. 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.

    48 min
  3. Golden Girls, Laverne & Shirley, Gary Shandling and the Stories Nobody Tells

    May 11

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

    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 IMDB Time Off for Bad Behavior The Comatose Adventures of Lenny Rose Kind of Dirty Paris Confessions Marc's website Follow Jeff Dwoskin (host): Jeff Dwoskin on Twitter The Jeff Dwoskin Show podcast on Twitter Podcast website Podcast on Instagram Subscribe to my Youtube channel Yes, the show used to be called Live from Detroit: The Jeff Dwoskin Show Ways to support the show: Buy me a coffee (support the show) Dashery/TeePublic Store: Classic Conversations merch and more! Love the books I talk about on the show? Here is my Amazon store to shop. 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.

    45 min
  4. Greg Evigan on BJ and the Bear, My Two Dads, TekWar, and a New Album

    May 4

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

    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 IMDB Greg's website Instagram Buy the album Facebook Follow Jeff Dwoskin (host): Jeff Dwoskin on Twitter The Jeff Dwoskin Show podcast on Twitter Podcast website Podcast on Instagram Subscribe to my Youtube channel Yes, the show used to be called Live from Detroit: The Jeff Dwoskin Show Ways to support the show: Buy me a coffee (support the show) Dashery/TeePublic Store: Classic Conversations merch and more! Love the books I talk about on the show? Here is my Amazon store to shop. 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.

    52 min
  5. How Gossip Girl Defined a Generation of TV Fans with Lindsay Denninger

    Apr 27

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

    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 Lindsay's website Lindsay's book Instagram Linday's substack Follow Jeff Dwoskin (host): Jeff Dwoskin on Twitter The Jeff Dwoskin Show podcast on Twitter Podcast website Podcast on Instagram Subscribe to my Youtube channel Yes, the show used to be called Live from Detroit: The Jeff Dwoskin Show Ways to support the show: Buy me a coffee (support the show) Dashery/TeePublic Store: Classic Conversations merch and more! Love the books I talk about on the show? Here is my Amazon store to shop. 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.

    36 min
  6. Lahna Turner on Ralphie May Legacy Love Loss and Come What May Documentary

    Apr 20

    Lahna Turner on Ralphie May Legacy Love Loss and Come What May Documentary

    Lahna Turner opens up about a journey shaped by creativity, loss, resilience, and reinvention. From a shy photographer hiding behind the lens to commanding stages as a comedian, her path was anything but predictable. A life-altering car accident pushed her to confront fear head-on, ultimately leading her into stand-up comedy and a deeply transformative relationship with Ralphie May. Her latest project, Come What May, is more than a documentary—it’s a decade-long labor of love capturing Ralphie May’s life, struggles, and legacy. Through raw storytelling, unseen footage, and personal reflection, Lahna reveals the complexities behind fame, addiction, grief, and healing. This conversation explores not only Ralphie’s rise and impact, but also the emotional weight of telling a story that’s both deeply personal and universally human. Show Highlights: How a near-death car accident pushed Lahna Turner to pursue comedy and abandon fear The unexpected love story between Lahna Turner and Ralphie May before fame Behind-the-scenes insight into Come What May and why it took nearly a decade to complete The truth about Ralphie May’s rise to fame and the pivotal role of Jay Mohr Lahna Turner’s personal growth, grief journey, and rediscovering love after loss Lahna Turner shares the emotional journey of creating Come What May and what it revealed about love, loss, and legacy You're going to love my conversation with Lahna Turner Lahna's website Come What May webssite Instagram YouTube Lahna on Amazon IMDB to squish a bug (daughter's book) Follow Jeff Dwoskin (host): Jeff Dwoskin on Twitter The Jeff Dwoskin Show podcast on Twitter Podcast website Podcast on Instagram Subscribe to my Youtube channel Yes, the show used to be called Live from Detroit: The Jeff Dwoskin Show Ways to support the show: Buy me a coffee (support the show) Dashery/TeePublic Store: Classic Conversations merch and more! Love the books I talk about on the show? Here is my Amazon store to shop. 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.

    46 min
  7. Jeff Altman The Real Story Behind a Life in Comedy and Television

    Apr 13

    Jeff Altman The Real Story Behind a Life in Comedy and Television

    Jeff Altman dives into the unpredictable reality of building a career in comedy, television, and entertainment, sharing behind-the-scenes stories from stand-up, acting, and life in Hollywood. From early days at iconic comedy clubs to landing television appearances and working alongside legendary comedians, this conversation reveals what it really takes to survive—and evolve—in the entertainment industry. With humor and honesty, he breaks down career highs, brutal lows, and the unexpected pivots that kept him in the game. Show Highlights: How asking directly for opportunities led to a first major TV appearance The reality of bombing in stand-up comedy—even on national television Building a long-term friendship with David Letterman early in a comedy career Working with iconic comedians like Rodney Dangerfield and Robin Williams The behind-the-scenes chaos of starring in a TV variety show with a language barrier Becoming a recurring television character and fan favorite on a hit series Navigating the ups and downs of a long-term career in Hollywood A career mistake that cost a multi-season TV opportunity Transitioning between stand-up comedy, acting, and voiceover work Reinventing a career later in life through close-up magic and live events You're going to love my conversation with Jeff Altman Jeff's website IMDB Follow Jeff Dwoskin (host): Jeff Dwoskin on Twitter The Jeff Dwoskin Show podcast on Twitter Podcast website Podcast on Instagram Subscribe to my Youtube channel Yes, the show used to be called Live from Detroit: The Jeff Dwoskin Show Ways to support the show: Buy me a coffee (support the show) Dashery/TeePublic Store: Classic Conversations merch and more! Love the books I talk about on the show? Here is my Amazon store to shop. 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.

    50 min
  8. Charlene I've Never Been To Me And The Journey From Motown To Redemption

    Apr 6

    Charlene I've Never Been To Me And The Journey From Motown To Redemption

    Charlene’s journey is a powerful reminder that timing, talent, and truth don’t always align the way we expect—but when they do, the impact can last forever. From humble beginnings singing at home to being discovered by Motown, her story unfolds through moments of raw emotion, unexpected opportunity, and industry heartbreak. The creation of her global hit reveals just how deeply personal music can be—and how the right song at the right time can change everything. Despite setbacks, missed opportunities, and financial injustice, her voice and legacy continue to resonate across generations, proving that timeless art always finds its way back. Show Highlights: Discovered unexpectedly after casually singing—leading to a meeting with Motown’s biggest names The intense recording process that transformed a deeply personal song into a timeless classic How the song initially failed—then became a worldwide hit years later through a random radio revival Behind-the-scenes realities of the music industry, including lost royalties and contract pitfalls Reflections on legacy, creativity, and why some stories—and songs—never fade You're going to love my conversation with Charlene Listen to Charlene's music on Spotify Follow Jeff Dwoskin (host): Jeff Dwoskin on Twitter The Jeff Dwoskin Show podcast on Twitter Podcast website Podcast on Instagram Subscribe to my Youtube channel Yes, the show used to be called Live from Detroit: The Jeff Dwoskin Show Ways to support the show: Buy me a coffee (support the show) Dashery/TeePublic Store: Classic Conversations merch and more! Love the books I talk about on the show? Here is my Amazon store to shop. 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.

    51 min
See All (426)

Trailer

4.9
out of 5
107 Ratings

About

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! If you love classic TV, if you love the movies, if you love film and tv interviews (see where I'm going with this), you'll love Classic Conversations with your host, comedian, Jeff Dwoskin.

Information

You Might Also Like