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
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.
I'm a tech entrepreneur, podcaster, and professional stand-up comedian. I started my journey in the tech industry back in 1997 when I founded my own website development company, which was one of the pioneering companies in the country at the time. While working in technology, my comedic talents couldn't be contained, and I eventually took to the stage as a stand-up comedian.
My passion for comedy led me to create Hashtag Roundup (@hashtagroundup on Twitter), a platform that has contributed to over 8000 top 10 USA trends on Twitter. With the growth of social media, particularly Instagram, I founded Stampede Social, a company aimed at helping creators drive traffic to their content without relying solely on a link in their bio.
