The night your back decides it runs your life, every choice turns tactical. That’s where we start: a no-move sleep position, a desperate attempt to dodge sciatica, and the inconvenient comedy of crying quietly at 4:30 a.m. without alarming the house. From there, the ride swerves through canceled gigs, algorithm pep talks that last exactly one second, and the weird economy of making people laugh while your spine negotiates with gravity. We get honest about money, pride, and the grind of being...
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The night your back decides it runs your life, every choice turns tactical. That’s where we start: a no-move sleep position, a desperate attempt to dodge sciatica, and the inconvenient comedy of crying quietly at 4:30 a.m. without alarming the house. From there, the ride swerves through canceled gigs, algorithm pep talks that last exactly one second, and the weird economy of making people laugh while your spine negotiates with gravity. We get honest about money, pride, and the grind of being...
The night your back decides it runs your life, every choice turns tactical. That’s where we start: a no-move sleep position, a desperate attempt to dodge sciatica, and the inconvenient comedy of crying quietly at 4:30 a.m. without alarming the house. From there, the ride swerves through canceled gigs, algorithm pep talks that last exactly one second, and the weird economy of making people laugh while your spine negotiates with gravity. We get honest about money, pride, and the grind of being...
A beach, a phone on 0.5 zoom, and a comedian trying to outrun a stubborn year—this one starts fast and refuses to walk it back. We kick things off with a flurry of winter tour dates and then throw ourselves into the Gulf-side chaos: strangers staring, cargo ships hulking on the horizon, and the mind game of recording while the world pretends not to notice. It’s messy, it’s loud, and it’s honest about what touring feels like when the budget is thin and the calendar is full. We dig into concer...
The day starts with a jolt: I wake up on the wrong piece of furniture and my back files a formal complaint down both legs. From there, everything turns into an offbeat survival guide—how to stand when you can’t, why stretching is the new humility, and what happens when laughter is the only thing that keeps a pain spiral from eating the whole day. Along the way I confess my love-hate with AI, the climate guilt that had me one click away from ordering bug protein, and the ridiculous debate over...
The plan was simple: leave St. Louis before the snow hits, beat the storm, make it back in time for tour. What actually happens is a slow-motion thriller on unplowed highways that morphs into a funny, unguarded exploration of fear, masculinity theater, and the messy work of healing. I talk through the white-knuckle ramps, the “sport mode will save me” delusion, and why following a semi at a respectful distance can feel like spiritual practice when the lanes disappear. Between jolts of panic ...
The day starts with fart etiquette and donuts and somehow ends with a heartfelt riff on friendship, parenting, and the strange rules of public bathrooms. That’s tour life: messy, loud, and full of tiny moments that turn into the stories we repeat for years. With our favorite chaos magnet Cactus Tate back on the mic, we stumble through airport bathroom mix-ups, “rocks don’t float” river logic, and the unflinching honesty that only comes from living shoulder to shoulder on the road. We go ther...
The day starts under a gray sky and a loud pavilion, and somehow that flimsy roof becomes a philosophy. We kick off by turning “you can’t corner me, I’m in a pavilion” into a whole worldview about space, safety, and the strange etiquette of public shelters. From there, the story jumps to Peoria’s Jukebox Comedy Club, where a broken chair and a grumpy Richard Pryor portrait spark a set built on pure presence. It’s a reminder that the best bits often arrive when you stop trying to force them an...
A closed hotel pool, a hot parking lot, and an angry ant hill aren’t the villains—they’re the chorus. Episode 100 lands mid-bite and mid-thought, which turns out to be the most honest place to take stock of a life on stage. We talk about addiction-level love for Story of the Year’s new song Gasoline, daydreams of skipping lunch for a KTM, and how the road strips away your excuses until only the work is left. That’s where the real conversation starts: anxiety that pretends to be effort, the st...
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....
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 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 chil...
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 pers...
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 finan...
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 Ma...
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 ...
Travel disasters have never been so entertaining! When my carefully measured carry-on luggage wouldn't fit in the overhead compartment and I spilled an entire coffee on the airplane floor, I knew this week was destined to become podcast gold. During a seven-hour Atlanta layover, I'm spilling more than just coffee—I'm sharing the beautiful chaos of life on the road. This episode takes you from Philadelphia casinos where my friends and I tested our luck at roulette tables (minus the alcohol th...
Ever caught yourself nodding politely while your Uber driver shares their life story at 3 AM? Or perhaps you've been that driver, watching a clearly intoxicated passenger try to maintain a conversation? This episode dives headfirst into the bizarre social ecosystem of rideshare culture from both sides of the app. Between announcing a packed summer tour schedule (come see me in Seattle, Portland, Oklahoma City, Philadelphia, and my Canadian debut in Edmonton!), I'm unpacking the strange intim...
What does it really mean to pursue a creative life on your own terms? Bobby takes us deep into his world as he navigates the unpredictable reality of being a touring comedian without a permanent address – something he calls "living flexibly" rather than homelessness. When tour plans to Canada suddenly change, Bobby finds himself celebrating the 4th of July with his friend Tatum's family instead of performing abroad. The unexpected detour leads to building a trampoline in the Texas heat for T...
Bobby returns to the podcast after a month-long hiatus with a delightful chaos of stories from life on the road. Recorded outdoors in Bakersfield, California—a city where "everything's on fire" and the famous nu-metal band Korn (with that backward "R") originated—this episode captures the beautiful mayhem of a comedian's touring life. From waking up in panic not knowing which city he's in, to the surprising contentment that comes with being "literally homeless and having the time of my life,...
The night your back decides it runs your life, every choice turns tactical. That’s where we start: a no-move sleep position, a desperate attempt to dodge sciatica, and the inconvenient comedy of crying quietly at 4:30 a.m. without alarming the house. From there, the ride swerves through canceled gigs, algorithm pep talks that last exactly one second, and the weird economy of making people laugh while your spine negotiates with gravity. We get honest about money, pride, and the grind of being...
