A sunrise at the Arch, a long overnight drive, and a confession most of us dodge: sometimes the tears just don’t stop, and the only thing that steadies you is the road. We head back to St. Louis to face a stack of old memories—prom photos, a busted elbow, a skyline that still knows too much—and use humor to navigate the heaviness. It’s raw without being bleak, funny without being flippant, and honest about how weird and human it is to cry next to someone you love while pretending you’re fine.

We dig into the small mechanics of hiding big feelings—the fake yawn, the damp sunglasses, the careful breath—and the bigger question of when to share and when to protect your own space. Emotions show up like antique store finds: pretty in the aisle, awkward at home, and tough to part with even when they don’t fit your life. We talk about being “on reserve” for other people’s loneliness, setting boundaries without burning bridges, and why the instinct to go numb can feel easier than being open. Along the way, there’s a rant about bench pressing, a case for gentler movement, and a reminder that presence often starts with a walk, a laugh, and a phone on airplane mode.

This story isn’t about perfect healing; it’s about staying with yourself long enough to hear what the feelings are saying and then deciding what to keep. If you’ve ever driven home just to remember why you left, or stared at a city that holds both joy and regret, you’ll recognize the pulse here. Press play, ride shotgun through the nostalgia and the noise, and leave with a lighter grip on what no longer serves you.

If this resonates, subscribe, share with a friend who might need it, and drop a review. Tell me: what place still messes with your heart, and what did it teach you to carry?

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What happens when you combine perfect hoodie weather, exceptionally potent cannabis, and sidewalks that require the vigilance of a bomb squad technician? Welcome to Portland, Oregon – a city that demands you look up at its breathtaking beauty while carefully watching every step.

The contradictions of Portland create the perfect backdrop for reflection. One moment I'm admiring the stunning architecture and fall colors painting the sky in magnificent hues, the next I'm dodging "dog" waste with the agility of an Olympic athlete. This constant shifting between appreciation and avoidance becomes a metaphor for life itself – finding beauty despite obstacles.

My adventures took unexpected turns, from dropping an AirPod on an airport bathroom floor (creating an existential hygiene crisis) to visiting what I can only describe as a "witch coffee shop" complete with tarot readings and crystal-infused beverages. The cannabis scene lived up to its reputation, leading to a sushi experience where I questioned whether decorative flowers were meant for consumption (they weren't, but I ate one anyway to the visible confusion of the chef).

The most profound moment came during an evening walk as dusk settled over the city. As the sky transformed through different shades of blue, I found myself overwhelmed with abstract gratitude – not directed at anything specific, just a general appreciation for being present in that beautiful moment. Sometimes thankfulness doesn't need a target; it can simply exist as recognition of the wonder around us.

From serendipitous encounters with strangers who became temporary companions to observations about the eclectic Sunday crowd, Portland revealed itself as a place that embraces individuality in all its forms. The city doesn't hide its flaws but somehow integrates them into its unique character, creating an authenticity that's increasingly rare in our world.

Ready to join me on more adventures? Check out our new merch at BobbyJcocks.com and catch me on tour with Cactus Tate – dates and locations on my website!

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The open road has a way of pulling profound thoughts from even the most distracted minds. Cruising down highways lined with autumn-kissed trees, this episode captures the stream-of-consciousness reflection that can only happen behind the wheel.

Bobby dives deep into the peculiar hill he's willing to die on – hot coffee versus canned coffee – and why he'll defiantly order a steaming cup even in the sweltering Texas heat. The conversation shifts to life's small revelations, like his first childhood discovery of cruise control and how it terrified him to see his aunt seemingly driving without feet on the pedals.

The meat of the episode tackles a modern philosophical dilemma: how much understanding should we extend to those who seem incapable of reciprocating? When someone cuts you off in traffic, are you obligated to imagine they're rushing to the hospital? Or is there a point where collective consideration breaks down when only some people practice it?

Throughout the journey, Bobby shares moments of connection that punctuate his nomadic lifestyle – attending Nikki Glazer Day at Busch Stadium, bonding with her family, and even getting invited to smoke with her neighbors. He reflects on the liberation that comes with emptying his storage unit, letting go of VHS tapes and memorabilia that once seemed essential to preserving his memories.

Whether you're a fellow road warrior or simply enjoy listening to unfiltered thoughts, this episode offers a window into the comedian's mind as he navigates both highways and life itself. Check out Bobby's website for new tour dates – he's booking shows and ready to bring his unique perspective to a venue near you.

What happens when musical talent meets comedic genius? In this episode, we dive deep with multi-talented creator Chandler Cooper, whose unique blend of music, comedy, and authenticity has captivated audiences across social media platforms.

Chandler takes us through his fascinating journey from performing Stitch impressions as a child to developing his distinctive musical style. With remarkable candor, he shares the stories behind songs like "Looking for Sarah" and "Funny," revealing how personal experiences transform into art that resonates with thousands. There's something magical about how Chandler crafts lyrics with meticulous intention while maintaining an openness to collaboration that many artists lack.

The conversation explores the delicate balance between influence and originality, with Chandler noting how the most successful artists draw inspiration without becoming carbon copies of their heroes. "I want to be in a room where I'm the dumbest in the room at something," he explains, highlighting a refreshing humility that seems central to his creative philosophy. This approach has allowed him to develop a voice that's unmistakably his own, whether he's crafting emotional songs or creating character-driven comedy.

Beyond music, we weave through surprising territory – from camping out in freezing temperatures to meet Bryan Cranston and Aaron Paul to the creative benefits of saying "yes" to unexpected opportunities. Chandler's recommendation of Matthew McConaughey's "Greenlights" underscores his philosophy of embracing life's journey with openness and authenticity.

If you've ever struggled to find your creative voice or wondered about the intersection of different artistic mediums, this conversation offers both inspiration and practical wisdom. Follow Chandler on tour this March hitting Denver, Omaha, Atlantic, Branson, and Oklahoma City by following @ChandlerCooperOnTour on Instagram for all the details.

Bob takes us on a wild journey through his recent gambling misadventures, road trip observations, and poignant reflections on aging in this deeply personal episode of Discombobulated.

The casino has a way of making us forget everything we know about math and probability. Bob's $240 loss becomes a springboard for exploring the psychology behind gambling – the magical thinking, the superstitions, and the desperate attempts to recoup losses that only lead deeper into the hole. Despite the financial setback, he finds humor in the situation, celebrating the small victory of not visiting the ATM or bumming a cigarette.

As summer draws to a close, Bob contemplates the bittersweet nature of seasonal transitions. He hilariously skewers the clichéd conversations about fall weather and pumpkin spice lattes while touching on something profoundly relatable – that end-of-summer feeling when we realize all the adventures we planned but never experienced. His take on fall as a time to "cozy up with all your sad thoughts" somehow manages to be both cynical and comforting.

The episode takes a vulnerable turn as Bob discusses turning 35. His emotional birthday – crying alone on a Vancouver balcony and realizing he couldn't remember the last time he blew out candles – captures the complex emotions of growing older. The changing nature of birthdays, from the expectation-filled celebrations of our twenties to the more introspective moments of our thirties, will resonate with anyone who's felt the passage of time.

Between philosophical musings, Bob delivers laugh-out-loud moments, including an unfortunate pants-soiling incident and observations about roadside attractions featuring Elvis. His talent for finding profound meaning in everyday experiences, all while making you chuckle, shines throughout.

Whether you're reeling from your own gambling losses, preparing for fall, or contemplating another trip around the sun, this episode offers the perfect blend of humor and heart. Don't forget to check out Bob's upcoming tour dates and join the Patreon to support the show!

Join Bobby on an epic road trip as he drives 24 hours from New York to Texas, sharing unfiltered thoughts from behind the wheel that range from hilarious to surprisingly profound.

When Bobby finds himself with an unexpected day in New York City before hitting the road, he makes the impulsive decision to attend Kill Tony at Madison Square Garden. Standing outside the legendary venue, he experiences a powerful full-circle moment, reflecting on his first-ever New York performance at the tiny Magnet Theater years ago. Though he doesn't get selected to perform among hundreds of hopefuls, the experience becomes a meaningful marker in his comedy journey.

The podcast takes an unexpected turn when Bobby recounts a run-in with NYPD officers after lighting up a joint in a park. Rather than panicking, Bobby's honesty and quick humor lead to a surprising outcome – the officers laughing so hard they tear up his citation. This story evolves into thoughtful reflections about privilege, human connection, and the value of owning your mistakes.

Perhaps the most memorable moment comes when Bobby describes a hotel room interruption at the most inopportune time – a front desk employee knocking repeatedly to charge for "incidentals" forgotten during check-in. Bobby's negotiation for free water and late checkout showcases his ability to find humor in awkward encounters while standing up for himself.

Throughout the episode, Bobby weaves between road trip observations, philosophical musings about life's random encounters, and practical advice about handling uncomfortable situations. Whether he's contemplating what he'd do with lottery winnings or critiquing people who drive with their feet out the window, his stream-of-consciousness style creates an intimate listening experience that feels like riding shotgun with a hilarious friend.

Have you experienced a full-circle moment in your life? Share your story and subscribe to hear more of Bobby's adventures on and off the road!

Dive into the unexpected as I broadcast live from a bubble bath in a Roman-themed fantasy hotel room in Edmonton, Canada! This episode captures the beautiful absurdity of comedian life on the road – homeless but somehow lounging in luxury accommodations that feel straight out of a movie.

The cultural differences between America and Canada come alive through everyday experiences that are slightly tilted from what we're used to. There's something fascinating about walking through a McDonald's drive-thru (they actually encourage it here!), sampling Canadian cannabis that hits differently than stateside varieties, and watching television that alternates between familiar American programming, French broadcasts, and content that would never make it past US censors.

Canadian hospitality takes center stage as I compare my elaborate Roman-themed room with its hand-painted ceilings to my tour mate's princess suite. Meanwhile, I'm constantly on alert for that quintessentially "Canadian" experience that seems perpetually just around the corner. When a fan recognizes my companion on the street, it's a reminder of how comedy connects us across borders.

Beyond the laughs, there's something genuinely thought-provoking about travel – how the extended daylight hours affect the rhythm of life, how subtle differences in everyday interactions reveal cultural values, and how a simple change of scenery can provide fresh perspective. As I contemplate life from this bubble bath, I'm struck by how a single decision to sign up for an open mic 15 years ago created a path that led to this perfectly ridiculous moment.

Join me for this uniquely intimate episode filled with observations about ugly locals, odd hotel features, and surprising cultural discoveries – all delivered with grateful reflection on the strange and wonderful journey of a touring comedian. After all, where else can you contemplate life's mysteries from a Roman bathtub in Canada?