Classic Conversations: Pop culture Interviews with Jeff Dwoskin

Comedian, podcaster and actor Jackie Kashian has been doing stand up since 1984, when she got thrown out of a Madison, Wisconsin comedy club for heckling Sam Kinison and came back three weeks later for the open mic.

She talks about featuring for Brian Regan and Maria Bamford, playing an airport cop on the final season of Murphy Brown, the year Mark Ridley's Comedy Castle told her she was too much like Kathleen Madigan to book, and why watching Jay Leno do two word perfect sets in 1987 rewired how she thought about the job. She also digs into The Dork Forest, the podcast she has been making since 2006, where the whole point is letting somebody talk for an hour about sandcastles, Rummikub or the size of A4 paper.

Throwback episode - originally recorded 2021

Show Highlights:

The Dork Forest. Jackie Kashian has been recording her interview podcast since 2006 and has close to 700 episodes in the archive, all built on one idea: an hour of somebody explaining the thing they love most. Guests have walked her through Remember the Titans beat by beat, Star Trek, Marvel comics, and competitive sandcastle building.

The Jackie and Laurie Show. Her weekly show with Laurie Kilmartin lives on the Maximum Fun network, and unlike The Dork Forest it is not evergreen, which means it gets recorded wherever she is, including one episode whispered into a laptop at a Kinko's in Milwaukee.

Murphy Brown. She played an airport cop on the 1998 final season and calls it typecasting, and she is honest that acting is a learned skill she has never formally learned.

Featuring for Brian Regan and Maria Bamford. These are the only two headliners she opens for now, and the reason is simple: it means she gets to watch Brian Regan and Maria Bamford every night.

Getting started in 1984. At 19 she got drunk in the front row of a club owned by Bill Kinison and heckled Sam Kinison, years before the Letterman and Rodney Dangerfield appearances broke him nationally. The manager told her open mic was on Sunday.

You're going to love my conversation with Jackie Kashian

Jackie's website

Instagram

The Dork Forest

YouTube

IMDB

Jackie's Merch

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.

Rhonda Shear hosted more than 400 episodes of Up All Night on USA Network from 1991 to 1998, and she is one of the only hosts from that era who still owns the name.

She talks about the Happy Days incident with Henry Winkler that got her blackballed from every Paramount sitcom at 23, the one line in Spaceballs that Mel Brooks cast her in himself, opening for Robin Williams at the Holy City Zoo, and how a Playboy pictorial where she kept all her clothes on cost her a pageant crown and made headlines around the world. She also explains how a warehouse in Tampa became the studio where she is producing brand new Up All Night episodes today, funded by the bra and panty company she built with her husband.

Show Highlights:

Up All Night on USA Network. Rhonda Shear hosted the show from 1991 to 1998 and estimates she has 400 plus episodes, but USA destroyed the masters when the network sold, taking a decade of Gilbert Gottfried material with them.

Spaceballs. Mel Brooks personally auditioned every tiny role, told her he wanted a blonde for the diner waitress, and hired her anyway when she offered to wear a wig. She has one line and gets asked about it more than anything else she has done.

Chuck Barris. She did The Gong Show, The Dating Game, the $1.98 Beauty Show, and a Barris pilot called Comedy Courtroom, and argues he was doing reality television decades before anyone called it that.

The pageant scandal. Her $1.98 Beauty Show appearance aired in the middle of the Miss Torrance pageant she was leading, the judges said she was mocking the pageant system, and she finished first runner up instead of advancing toward Miss America.

Playboy and the Floral Trail. Her 1977 Girls of the New South pictorial was shot fully clothed in antebellum dress at New Orleans plantations by photographer David Chan, and the Floral Trail Society stripped her of her queen title over it anyway.

Stand up in the 1980s. She worked the Improv, the Laugh Factory, and the Comedy Store, introduced Robin Williams at the Holy City Zoo and effectively became his opening act, and pitched Jamie Masada on a women of comedy night she booked and filled herself.

You're going to love my conversation with Rhonda Shear

IMDB

Up all Night Network

Rhonda's Book

Instagram

YouTube

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.

Rebeca Arthur was hired for one week on Perfect Strangers and stayed eight years.

Before that she was a working private investigator in New York, and one of her agency's cases was Robert Durst. She talks about playing Mary Anne Spencer opposite Bronson Pinchot's Balki Bartokomous, photocopying her own backside for Scrooged, improvising with Bill Murray, getting career advice from Bob Newhart at a table read, and the dog who got a SAG paycheck out of Match Game. Forty years after Perfect Strangers premiered, she is still working, still funny, and still friends with almost everyone she has ever worked with.

Show Highlights:

Perfect Strangers. Rebeca Arthur auditioned for Jennifer, read the Mary Anne sides on the back page, and told the casting director she wanted the other part instead. The one week guest spot turned into eight years, and she and Melanie Wilson were on the phone with each other, using call waiting, when the calls came in telling them they were coming back.

Private investigator years. She could not get a waitressing job in New York, so she answered an ad, was told she would never make it as a PI because she was too noticeable, and immediately decided that was the job she wanted. She worked cases for three years while finishing school.

The Robert Durst case. Her agency was hired by Durst after his wife Kathie went missing, but only to field the tips coming in off his reward offer, never to look for her. Her boss Jerry kept telling the staff their hands were tied while Kathie's own family called the office demanding answers.

Scrooged. A production assistant walked her down to an office to photocopy her rear end for the film, and yes, it was actually hers. Bill Murray built the whole scene with her on the spot, kept forgetting what he had just improvised, and had her feed his own lines back to him between takes.

Newhart. Bob Newhart lowered his newspaper at a table read, listened to her worry about a prop gun in a play she was doing, and told her to walk to the phone right then and quit. She calls him one of the most generous actors she ever worked with.

You're going to love my conversation with Rebeca Arthur

IMDB

Instagram

Cabi store

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.

Thirty years after the last shot was fired, the bank robber and the FBI agent who chased him are sitting down together.

Steve Meyers helped Scott Scurlock pull off the Hollywood Bandit crime spree that hit 19 Seattle banks and took roughly $2.3 million between 1992 and 1996. Shawn Johnson was the FBI case agent who spent four and a half years hunting them. Both appear in the Netflix documentary How to Rob a Bank, and both say the film left out the story that actually matters, which is why they reconnected, why they are now friends, and what really happened on Thanksgiving Eve 1996.

Show Highlights:

How to Rob a Bank (Netflix). Steve Meyers and Shawn Johnson break down what the documentary got right, what it padded with filler, and why the cartoon reenactments were lifted from Steve's unpublished manuscript without credit.

The Treehouse. Steve wrote the book in his first year and a half in prison as stream of consciousness, then edited it down over the years, and Shawn says reading it put him back inside the case with details he never knew as the lead agent.

The reunion. Shawn tracked down Steve's phone number after the Netflix release, then drove the friendship forward after reading the book, and Steve brought the original prison manuscript to Virginia for a four day sit down last November.

Scott Scurlock, aka Hollywood. Steve describes the man behind the disguise as a chameleon with a different personality for everyone, a builder and volunteer wildland firefighter who studied FBI journals to learn why other bank robbers failed.

The lawsuit nobody talks about. Six months after the shootout, Detective Mike Magan and four other officers sued Scurlock's parents for $250,000 apiece for trauma, and Steve calls it the strangest footnote in the entire case.

You're going to love my conversation with Steve Meyers and Shawn Johnson

IMDB - How to Rob A Bank

The Treehouse (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.

Douglas M. Wilson has been in the room for some of the strangest and most memorable television of the last thirty years.

A four time Emmy nominee, he went from being an assistant at MTV to the Comedy Channel, then spent the better part of a decade on Politically Incorrect with Bill Maher, rising from associate producer to showrunner. From there he built an entire second career in unscripted television with LA Ink, The Pickup Artist, American Inventor, Best Week Ever and Paris Hilton's My New BFF. He breaks down how the Politically Incorrect panel was engineered, why Bill Maher was far kinder than his on air reputation suggests, and why he believes a bad profit deal, not the 9/11 comments, is what actually killed the show at ABC.

Show Highlights:

Buffalo and Broadway. He grew up flying to New York for weekends of four and five shows, directed A Day in Hollywood and A Night in the Ukraine in college, and walked away from theater directing once he did the math on a decade of apprenticing for free.

The Comedy Channel. His first television job was as Janet Scardino's assistant at MTV, and he left for the Comedy Channel, an office full of comedians where he worked on Night After Night with Allan Havey, The Higgins Boys and Gruber and Rachel Sweet's show.

Politically Incorrect with Bill Maher. Scott Carter brought him on as an associate producer and he left in 2000 as showrunner, and he lays out the four chair formula behind every panel, why John Waters was the best guest they ever had and musicians the worst, and how generous Bill Maher was about his work despite agreeing on almost nothing personal. He blames an ABC demand for Tom Cruise, not the 9/11 comments, for the end of the show.

20th Television and Best Week Ever. A two year overall deal produced four shows total, and the Best Week Ever pilot he built and called in every favor for was taken away from him when VH1 moved production to New York.

The Eyes of Nye. He spent a stretch commuting to Seattle to work with Bill Nye, who he calls the genuine article, a host who would not let anything scientifically wrong get on the air.

The Pickup Artist. He cast men who genuinely could not talk to a woman, which turned Mystery's seduction series into a show about making a real connection, and he is proudest that couples ended up watching it together.

American Inventor. A short run with Simon Cowell's Syco and showrunner Clay Newbill, where he ran the studio episodes and found the format flawed, closer to a pitch competition than the invention challenge the title promised.

LA Ink. He read several books on tattoo culture before taking the job, worked with Kat Von D, Corey Miller, Hannah Aitchison and Kim Saigh, got tattooed by Kat Von D on live Fox 11 news, and watched TLC's push for personal drama drive the original artists out.

Paris Hilton's My New BFF. He kept his distance by design and handed the relationship to a younger producer, and he describes a human chain on a Tokyo rooftop to hold back fans plus a final elimination twist that is genuinely ruthless.


You're going to love my conversation with Douglas M. Wilson

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.