A 1960s Holiday Adventure

In this festive, retro-themed episode, Craig, Kenn, Ron, and guest host Randy swap stories about holiday shopping in the 1960s. Ron and his younger brother Randy revisit one of their family’s most legendary tales—five-year-old Randy’s epic struggle to make quick decisions, thanks to his intensely analytical mind, and the surprising consequences that followed.

During a long day of shopping, their parents try motivating the kids—Ron (8), Randy (5), and Sandy (3)—with the promise of a toy at the end of the trip. While Ron and Sandy eagerly snatch up their prizes, Randy’s endless deliberation tests everyone’s patience, ultimately costing him his toy and earning him an unforgettable lesson.

Ron and Randy share several hilarious moments from childhood that highlight a young Randy’s analytical (and often comically slow) approach to decision-making.

Join us for a nostalgic, laugh-filled journey back to the days of childhood, family shopping trips, and holiday memories!

• Boomer rating: Under the Edge.

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Guest host Keith joins the show to help recount one of the most legendary Boomers on the Edge stories—the night at the Duchess.

It’s late, they’re underage, and the Buds (John, Keith, Ray, Kenn, Craig, and Ron) have wandered into the Duchess, a notoriously grimy Detroit strip bar. It’s Kenn’s very first time in a place like this… and his reaction does not disappoint.

While most of the Buds rush to claim their spots around the stage, Kenn and Ron hover awkwardly near the entrance, trying to process the scene. Before long, Kenn starts whispering to Ron that the bar is “scummy”—a whisper that quickly escalates into his unmistakable “passion voice.” Within moments, he’s shouting across the bar, “They’re all scum!”

Ron panics, patrons turn, and the bouncer decides he’s seen enough. With a looming brawl on the horizon, he boots the entire group out in one sweep. And just like that, the Buds’ night is over.

This episode is pure comedy from start to finish—a true Boomers on the Edge classic. Buckle up—it’s a riot from start to finish.

• Adult themes and language.
• Boomer rating: On the Edge.

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In this laugh‑out‑loud episode, Craig shares a wild workplace story about a young apprentice who couldn’t stop bragging about his wife’s beauty—complete with revealing photos. The apprentice proudly flashes a picture, declaring, “This may or may not be my wife.”

That’s when Craig hatches a prank: each day, he shows the apprentice increasingly risqué photos of “his own wife”—images secretly pulled from the internet. The game quickly escalates into a hilarious competition of one‑upmanship, with both sides trying to outdo each other in the battle of “may or may not be their wife’s” pictures.

Tune in for this outrageous tale of workplace mischief, playful rivalry, and comedic escalation. It’s bold, funny, and guaranteed to entertain!

• Adult themes and language.
• Boomer rating: Way over the Edge.

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Kenn, Craig, and Ron return—and things get a little… fuzzy. Literally.

In this episode, Kenn dives into a wild piece of pop-culture news: Kim Kardashian’s SKIMS “Faux Bush” underwear line. Yes, you heard that right—G-strings with faux pubic hair, and apparently, they’re flying off the shelves.

The Boomers weigh in on this retro revival, sharing their reactions and swapping stories about the evolution of “the bush,” from the unshaven images they stumbled across as kids to the clean-shaven surprises they encountered at gentlemen’s clubs in Windsor, Canada during their early business days.

It’s a funny, nostalgic, and surprisingly enlightening stroll through decades of personal grooming trends—Boomers on the Edge style. Just like bell-bottoms from the ’70s, the bush is officially back!

• Adult themes and language.
• Boomer rating: Over the Edge.

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Remember when sneaking a peek at a National Geographic felt like the height of scandal? In this laugh-out-loud episode, Kenn, Craig, and Ron take a cheeky stroll down memory lane, contrasting today’s “so what” attitude toward nudity with the wide-eyed wonder of growing up in the 1960s.

Kenn kicks things off with a headline he read: Jennifer Lawrence appeared fully nude in a film… and the public reaction was basically, “meh.” In an age where nudity is everywhere online, the shock, mystery, and taboo that once surrounded it have all but vanished.

That sets the stage for Kenn, Craig, and Ron to reflect on just how different things were when they were growing up in the 1960s—when young boys had to get creative in their quest to see a bare breast. From sneaking peeks at National Geographic to stumbling upon discarded adult magazines, the crew swaps stories of their hilariously determined (and often disastrous) discoveries.

It’s a mix of comedy, cultural reflection, and a little bit of education—Boomers on the Edge style.

• Adult themes and language.
• Boomer rating: Over the Edge.

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Kenn shares a college Judo class story in which a training partner’s unexpectedly bold flirting puts him in an awkward spot. As Kenn describes trying to stay respectful and composed, Craig and Ron can’t resist teasing him about his reactions—and his younger self’s romantic cluelessness.

When the classmate eventually hands Kenn her phone number, his dramatic decision to tear it up sparks even more incredulous (and hilarious) commentary from Craig and Ron. Their relentless ribbing turns the tale into a running joke that carries through the episode.

To top it off, the show closes with outtakes of Craig and Ron’s outrageous reenactments of Kenn’s “moves,” delivering one last round of over-the-top hilarity.

• Adult themes and language.
• Boomer rating: Way Over the Edge.

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Fast Food, Exact Change and Synchronicity

Guest host Randy takes us on a hilarious trip down memory lane with two unforgettable fast-food encounters — one from behind the counter in the 1970s and another from the customer side in the 1980s.

First, we hear about Randy’s teenage pride and joy — his 1967 Chevy Nova II — and the fateful parking-lot standoff with his McDonald’s manager that ended with a torn-up paper hat and a pink slip. (Don’t worry — karma, and corporate, came for that manager soon enough!)

Then, as a customer years later, Randy finds himself in another fast-food fiasco — this time over a handful of olives at Subway and a perfectly counted pile of coins that sends a sandwich artist into orbit.

In both stories, synchronicity strikes when Randy unexpectedly crosses paths with his former foes, leading to laugh-out loud, full-circle moments you’ll have to hear to believe.

Get ready for nostalgia, comedy, and a reminder that sometimes the universe really does serve things up with a side of irony!

• Adult themes and language.
• Boomer rating: On the edge.

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Bachelor Party: The Aftereffect

Part III of the Bachelor Party Trilogy

It’s the late ’80s—VHS tapes, bad decisions, and one bachelor party that refuses to stay buried. In this outrageous finale, a mysterious coat left at Kenn’s house turns out to hide more than just bad decisions—it’s got drugs in the pocket, setting off a chain of chaos nobody saw coming.

When Ron is asked by a crazy sales manager Tom to bring the infamous bachelor party VHS to a New Year’s Eve gathering, things spiral out of control. Just after the midnight ball drop, Tom pops the tape into the VCR—right in front of the company’s VPs, executives, and their horrified wives. The room clears faster than the champagne bubbles, and Ron takes the fall for the whole fiasco.

Back at work, Tom adds insult to injury—mocking Ron by pretending to crank an old movie camera through the office halls. But the laughs keep rolling as management calls Ron in for “a serious talk” while Tom pantomimes outside the door.

A comedy of errors, misunderstandings, and pure 1980s office madness—Bachelor Party: The Aftereffect is the unforgettable finale of the Bachelor Party Trilogy.

• Adult themes and language.
• Boomer rating: Over the Edge

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