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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,...

Freedom calls from the wide-open road as Bobby makes a life-changing decision to abandon apartment living and embrace nomadic comedy life. After a frustrating apartment hunt culminating in a deceptive 15-month lease attempt, Bobby walks away from conventional housing altogether in favor of living out of his car while touring the country. This raw, honest episode captures the moment of transition as Bobby prepares to leave his Austin apartment for good. He calculates that out of the thirteen ...

Strap in for a wild ride as Bobby takes you on his recent adventure to New Jersey, where what started as a surprise appearance at his friend Venetia's 30th birthday spiraled into a week-long celebration that defied all expectations. From the moment he revealed himself on the balcony (causing tears of joy) to the hibachi dinner complete with sake squirted from water guns, every moment pushed the boundaries of adult fun. The Atlantic Ocean beckoned at midnight, frigid and foreboding, yet impos...

Ever been so enraged in traffic you contemplated getting out of your car to flip someone off? Bobby explores this universal frustration with hilarious candor, sharing his recent experience acting as a road rage surrogate for his friend. It's not just about anger—it's about human connection in our modern world where we've traded physical confrontations for symbolic gestures. Bobby takes us along on his recent comedy tour journey from Salt Lake City (where legendary comic Rory Scoville was per...

Ever found yourself digging metaphorical (or literal) holes you can't escape from? This episode dives deep into the beautifully chaotic reality of living with ADHD, territorial beach behavior, and those moments when we become the unexpected villains in our own stories. Fresh from Naples, Florida (affectionately dubbed "Nipples, Florida"), I share my passionate dedication to beach hole digging that sparked an unexpected feud with a family over borrowed shovels. There's something primal about ...

Bobby Rackleff chronicles his wild adventures as a touring comedian in this honest, hilarious episode that perfectly captures the beautiful chaos of life on the road. From accidentally being marked as needing special assistance at the airport (despite having never requested it) to the nightmarish experience of staying in a Travel Lodge smoking room that felt haunted by the souls of previous occupants, Bobby's travel misadventures will have you laughing and cringing in equal measure. The epis...

Ever wonder what really happens when comedians hit the road together? Bobby takes us behind the curtain of comedy touring life, revealing both the hilarious disasters and tender moments that unfold when performers spend too much time in close quarters. The adventure begins with a midnight dog hunt at Cactus Tatum's house before a painfully early flight. The panicked search through rainy streets ends with relief when the runaway pup is found at a neighbor's home—but it's just the first challe...