The 90s usually get called hip hop's golden era.

But the foundation was crafted in the 80s.

I went live with journalist and cultural critic Jeff Chang, author of Can't Stop Won't Stop, to talk about the records that changed the game — from Blondie's "Rapture" to It Takes a Nation of Millions to Hold Us Back, from Run-DMC to Eric B. & Rakim.

Then we talk about the greatest Gen X rappers of all time.

Jeff drops some science here. Straight from the dome. I thought I knew everything there was to know about 80s hip hop.

Man, was I wrong.

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MTV was the center of the pop cultural universe in the '80s and '90s. Then, just like that, it wasn't.

Dave Holmes had a front-row seat to both the meteoric rise and shocking fall of the network that defined Gen X.

As an MTV VJ from 1998 to 2003, Holmes hosted iconic shows like "TRL" and "120 Minutes," interviewing everyone from Tom Cruise to Joe Strummer during the channel's peak years.

But Dave also witnessed the critical mistakes that killed the video star—and they weren't what most people think. While many blame reality TV or changing viewer habits for MTV's decline, Holmes points to a corporate decision that sealed the network's fate.

Today, Dave has successfully reinvented himself as editor-at-large for Esquire and producer and host of the popular podcast series Who Killed the Video Star? and Waiting for Impact.

Dave is living proof that career pivots are possible even when entire industries collapse.

In this interview, we talk about:

• Being a closeted gay teenager in a conservative Catholic family in 1980s St. Louis

• His first memories of MTV and how it changed the way he saw the world.

• Dreaming of being an MTV VJ while DJing at a tiny local radio station as a 15-year-old.

• The 4 AM decision to audition for MTV's "Wanna Be a VJ" contest despite his inner voice saying "you're too old" at 27

• Losing to Jesse Camp but parlaying runner-up status into hosting TRL and 120 Minutes and more.

• Why MTV isn't what it was

• Reinventing himself from TV host to magazine editor and podcast producer.

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Andy Buckley never expected to become David Wallace, one of television's most recognizable bosses. But a chance encounter at a farmer's market changed everything. In this Small Talk conversation, the Gen X actor tells the story of his surprising second act from a financial advisor in corporate America to CFO of Dunder Mifflin on The Office. He also shares stories from the set working with Steve Carrell, Jenna Fischer, and Melora Hardin, why The Office continues to be so popular decades after it stopped production, particularly with Gen Z, and the current state of Hollywood production for 50-plus actors.

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Alison Tatlock, executive producer and writer on the hit TV show Pluribus, breaks down why the show resonates so strongly, especially with Gen X viewers raised to question authority, resist groupthink, and trust their own instincts.

We talk about:

• Why Pluribus sparks debate instead of offering answers

• How Gen X distrust shapes the show's central character

• The fear of being left behind by "progress"

• Grief as a quiet engine of the story

• Happiness as something imposed, not chosen

• Why belonging can feel like a threat

• The comfort and danger of consensus

• What refusing the hive actually costs

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Here's a shocking revelation: You know Norm and Cliff from Cheers? They were 37 and 38 years old at the height of that show's popularity. The old dudes in Cocoon were in their 40s! Why did men look so much older back in the day? Investigative reporter Steven Greenstreet, host of the Make This Make Sense at the New York Post, joins the show to explain why men from earlier generations aged so differently. Steven also debunks the latest UFO myths and shares his Gen X obessions, from The X-Files to Radiohead.

Author Max Brooks grew up surrounded by Hollywood royalty, but he never felt like he fit the part. Before World War Z and before he advised the U.S. military on disaster planning, he was the child of Mel Brooks and Anne Bancroft, who obsessed over niche interests and tried to survive school one awkward lunch at a time. In this episode, Max explains why being an outsider became his greatest advantage, how Gen X turned nerd culture into a superpower, and what happens when you finally stop pretending to be someone else. We talk zombies, obsessive research, and the strange freedom that comes from not caring whether anyone thinks you're cool. Max shares the long road from dismissed ideas to global influence. If you've ever felt different, this conversation hits home.

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More on Max Brooks

More than three in five Gen Xers are not confident in their ability to achieve a dream retirement and nearly half think they'll outlive their savings. We have far less confidence in our futures than generations before us. Kerry Hannon and Janna Herron, co-authors of Retirement Bites: A Gen X Guide to Securing Your Financial Future, explain how we got here and what we can do about it. They offer some useful, realistic tips about how to retire happily, even if it might not happen as soon as you'd like, including:

• How to build meaning and purpose into the second half of life.

• The mindset traps that keep us stuck, and how to break them.

• Reasonable retirement numbers for a typical Gen Xer.

• Biggest money leaks Gen Xers make.

• What a realistic reinvention timeline looks like

• Understanding Social Security, retirement accounts, and healthcare.

• Getting out of credit card debt.

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Former Hollywood TV writer Amy Suto walked away from her dream job to build a seven-figure writing business. She has a new book out called Write for Money and Power: The Anti-Starving Artist's Guide to Becoming a Seven-Figure Writer, which argues that writers need to stop romanticizing poverty and start building sustainable businesses. In this conversation, she reveals the three pillars creatives should focus on if they want to make money. Topics include: why self-publishing beats traditional deals, how she made $300K on Upwork, the Substack tweaks that added $100K in value, where freelance writers actually make money in 2025, why cold emails still work, and how to stop romanticizing the starving artist myth. This interview is packed with actionable strategies you can use today.

Small Talk

Amy Suto