Discombobulated with Bobby Jaycox

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 Tatum's daughter and reflecting on how children understand (or don't understand) the value of time, money, and presence. Through these everyday moments, he unveils profound observations about human connection and what truly matters.

The episode takes a humorously chaotic turn when Bobby attempts to record outdoors and battles with aggressive ants – a perfect metaphor for his larger philosophy about embracing life's unexpected challenges rather than fighting against them. "Do you want to live a life where ants don't sometimes get in your pants?" he asks, suggesting that a too-comfortable existence might actually be the more boring option.

Bobby's raw honesty about finally tackling years of overdue taxes (including a year he made just $14,000 as a comedian) and choosing to live without an apartment despite others' judgments reveals the courage it takes to design a life that brings personal joy rather than meeting external expectations. His vision of becoming "a comedian on the road who owns a dirt bike in the back of a fucking van" may not be conventional, but it's authentically his.

Whether you're questioning your own path or simply enjoy witnessing someone navigate life's complexities with humor and heart, this episode offers a refreshing perspective on finding freedom through embracing chaos rather than fighting it. Catch Bobby on tour this July across multiple cities – details in the episode!

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

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," Bobby shares a refreshingly honest perspective on choosing adventure over conventional adulthood. The contrast between friends with mortgages and his nomadic existence creates a fascinating exploration of different paths to happiness.

The episode weaves through recent adventures in Cleveland (where the clubs are getting too loud for his advancing age), beach trips with friends, and the peculiar experience of being complimented by strangers simply for walking with "babes." Bobby's stream-of-consciousness style leads to hilarious tangents about microphones that have seen better days, the geography of Batman's Gotham City, and the puzzling invention of Pokéballs.

Looking forward, Bobby announces his upcoming headline show in St. Louis on June 20th, his plans to see Story of the Year perform, and his first-ever international trip to Canada—where he'll ironically be celebrating the 4th of July. His genuine excitement about these experiences reminds us that sometimes the most fulfilling life isn't found in stability, but in embracing the unknown.

Subscribe, share with friends, and catch Bobby's headline show at St. Louis Helium Comedy Club on June 20th!

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

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 months he's paid rent, he's only spent about four to six months actually living there—a realization that makes his decision surprisingly clear. With characteristic humor, he recounts the apartment hunting nightmare: misleading agents, occupied apartments being shown by mistake, and the final straw of a suspiciously long lease term that sent him literally running for the door.

The conversation shifts to his unexpected back injury (pulled while coughing—the same thing that happened during his last move) and ambitious plans for the road. Between dreams of buying a dirt bike before securing housing and reflections on creative focus, Bobby shares a surprisingly philosophical perspective on choosing freedom over stability. "Anytime I've ever slept in my car, I always just feel like I'm doing the thing I've always wanted to do," he confesses, revealing how this seemingly radical choice actually aligns perfectly with his values and aspirations.

Whether you've ever questioned conventional life choices or simply enjoy Bobby's unique perspective on the comedy lifestyle, this episode offers both laughs and genuine inspiration. Check out his upcoming tour dates in Cleveland (May 30-31) and Austin (June 6-7), and consider supporting his Patreon for just a dollar—he'll even send you stickers from the road!

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

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 impossible to resist. Bobby recounts his reluctant plunge alongside his fearless friend Dom, capturing that perfect blend of regret and exhilaration that comes with doing something simultaneously stupid and memorable. Then there was Atlantic City's water park, where grown adults rediscovered childlike joy on slides that delivered unexpected thrills, punctuated by Bobby's humbling attempt at simulated surfing that ended with spectacular failure.

In perhaps the most surprising turn, Bobby found himself transformed into Britney Spears for a 2000s-themed party, where his costume became so convincing that partygoers bypassed his comedian credentials entirely: "We don't give a flying fuck about that. You're Britney Spears." Against this backdrop of unbridled fun, Bobby contemplates his return to reality—an emptying apartment, potential homelessness, and big decisions about his living situation. Yet through it all runs a thread of wisdom about embracing change and pushing through discomfort rather than avoiding it.

Ready for more Bobby adventures? Catch him in Cleveland at Don't Tell Comedy (May 30-31) and headlining the Velveeta Room in Austin (June 6-7). Come witness this comedian who might technically be homeless while performing—unless you want him going back to firefighting. Because as he warns, you won't be laughing when he's the one coming to save you from a burning building.

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

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 performing next door) to downtown Los Angeles (where he accidentally wandered near Skid Row). The constant thread through these adventures? His unmedicated ADHD brain noticing everything from bad paint jobs in bathrooms to the psychological warfare of airplane deplaning etiquette.

The most touching moments come when Bobby reflects on the friends who supported his early comedy career—those who showed up to open mics and struggled to find positive feedback beyond "everything you did up there was English." This raw honesty about the comedy journey resonates whether you're pursuing your own creative passion or just trying to figure out how to navigate social interactions without losing your mind.

With his signature unfiltered style, Bobby reminds us we're all just trying to figure life out, whether we're giving middle fingers on highways or watching our friends chase their dreams while wondering if they'll ever "make it." Sometimes the most human response is simply acknowledging our shared frustrations and finding humor in the chaos.

Come see Bobby headline in Cleveland (May 30-31) or Austin at the Velveeta Room, and check out his Patreon for exclusive updates about upcoming shows in your city.

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

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 defending your sandy territory from strangers who don't respect the craft of hole construction! My frustration with these "shovel thieves" reveals a larger theme – those moments when we feel justified in our reactions, only to question them later.

The sunscreen saga with fellow comic Tatum highlights our stubborn resistance to learning from experience. Despite clear evidence that "I don't burn" was categorically false after day one, she questioned needing protection again on day two! It's the perfect metaphor for how we sometimes refuse to accept reality despite painful consequences.

My Easter adventures back home take an awkward turn when I confront children I believe are stealing eggs we'd hidden for Tatum's daughter, only to discover they were part of a neighborhood scavenger hunt. These moments of misplaced righteous indignation – followed by the awkward realization of my mistake – capture the essence of being imperfectly human.

From making "booger bets" at airports to navigating lost luggage situations, this episode celebrates finding humor in life's frustrations. I'm learning to embrace my "diva bitch era" while acknowledging when my reactions might need tempering with understanding. After all, aren't we all just digging holes and trying to protect what matters to us?

Come see me on tour this spring! Dates in Salt Lake City, California, Cleveland, and Austin are all on sale now. Your support means everything – because yelling at beach families and misunderstanding Easter egg hunts doesn't actually pay the bills.

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

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 episode shines brightest when Bobby recounts his time in New York City, his favorite place in the world, where he spent quality time with friends Carly Aquilino and others. Despite getting only an hour of sleep after talking until 5 AM, the joy of these connections fuels his comedy. With refreshing candor, Bobby discusses the financial realities of being a working comic—how the constant need to save money leads to questionable hotel choices, and how sometimes splurging an extra $50 for comfort is worth it for your mental health and performance quality.

Whether describing his broken three-wheeled luggage, getting bitten by a "nice but also mean" cat, or his momentary existential crisis upon meeting identical twins (one of whom was a former pastor), Bobby's storytelling perfectly balances vulnerability with laugh-out-loud observations. His experiences wandering through malls and discovering that Spencer Gifts somehow still exists taps into a delightful nostalgia that many listeners will relate to.

Ready for more Bobby? Catch him on tour with Cactus Tate in Florida, Salt Lake City, and various California venues through May. Support the show on Patreon for exclusive bonus content starting at just $1 monthly and experience the beautiful, chaotic life of a comedian on the rise!

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

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 challenge of many. Bobby perfectly captures that stomach-dropping feeling of potential disaster, comparing it to "when the teacher hands you your paper face down."

Things escalate dramatically at the airport when Tatum suddenly falls ill, leading to an emergency cleanup operation and the purchase of a bright yellow Pittsburgh Pirates hoodie. The incident sparks a friendly rivalry as Bobby defends his response to the crisis: "You want me also to go vomit?" Their friendship endures through these messy moments, revealing how road partners take turns supporting each other through the chaos.

The tour takes them through Soul Joel's Comedy Club in Pottstown (where they're treated exceptionally well) and the Pittsburgh Improv (where audiences react in their own unique way). Bobby shares insights about the unwritten rules of touring relationships—like quietly cleaning hotel rooms without acknowledgment until the one time you forget and someone notices. These small gestures reveal the delicate balance between headliners and feature acts.

Between stories of farting on the road and accidentally calling venue managers by the wrong name, Bobby captures the beautiful absurdity of comedy life. Join him for upcoming shows with Emma Willman, Cactus Tatum, and solo dates across the country—just check the links to find tickets and witness the aftermath of these road stories firsthand.

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

Bob Jaycox greets his "she's, he's, they's and gay's" with the unmistakable warmth and self-deprecating humor that's made Discombobulated a favorite among comedy podcast fans. This episode finds Bob in rare form as he riffs on the peculiar satisfaction of embracing your own body odor, particularly when you're "stinking and trying your hardest."

With knees that sound like "when you should take the popcorn out of the microwave," Bob explores the unique indignities of aging into your mid-30s. Just when you think you've figured life out, your body starts betraying you in increasingly vocal ways. The podcast takes a surprisingly philosophical turn when Bob contemplates the nature of the afterlife, wondering if hell simply stinks like a grandparent's house, while heaven smells like a rich person's home—clean, but with a hint of "we're better than you."

One of the episode's most cathartic moments comes when Bob describes hurling his Google assistant against the wall in a fit of rage. "I threw that thing like the first pitch of a game, but I'm like a governor who doesn't know how to throw," he confesses, reveling in the pure satisfaction of destroying something that had been causing him frustration.

The episode culminates with Bob's excited plans to visit Brazil for the first time to see his favorite band, Story of the Year, perform. His attempts to learn Portuguese lead to a hilarious struggle with technology that somehow leaves his Google assistant speaking Portuguese and refusing to stop. Between announcing tour dates across Pennsylvania, Connecticut, Florida, Utah, and California, Bob manages to deliver an episode that feels like hanging out with your funniest, most unfiltered friend.

Whether you're battling your own aging body, contemplating infinity, or plotting your escape to South America, this episode of Discombobulated reminds us it's okay to embrace the chaos. Listen now, and remember—as Bob says—you don't have to be good, just don't be bad.

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox

Help Erin and her family here:

https://www.mealtrain.com/trains/w0kvdq

Sometimes life throws the hardest challenges at the best people. My childhood friend Erin, who shaped my musical tastes and shared countless teenage adventures with me, is now battling Guillain-Barré Syndrome – a condition where her immune system attacks her nervous system. As a mother of twins and other children, she needs our community's support now more than ever. Throughout this episode, I share memories of our friendship, from introducing me to Story of the Year (when they were still Big Blue Monkey) to navigating the awkward terrain of high school relationships.

Between urgent calls for support, I take you behind the scenes of the Two Hit Wonder Tour across California. From the historic walls of Cobb's Comedy Club in San Francisco (where comedy legends like Robin Williams once performed) to connecting with seemingly unreachable audience members at Sacramento's Punchline, these road stories highlight why comedy remains my perfect happy place despite its challenges. Plus, you'll hear about airport absurdities – from humiliating singing cupcake machines to the peculiar ways TSA consistently profiles my tour partner while I breeze through security.

This episode also marks a personal turning point as I share my journey quitting vaping, establishing a workout routine, and taking control of my finances. After some challenging years, I'm embracing positive changes while maintaining the silly personality that defines my comedy. As a particularly meaningful Coheed and Cambria lyric reminded me recently, "People call it luck, but they're just trying to pass the buck" – success requires both good fortune and persistent effort. Check my social media for links to help Erin, and come see us on the Two Hit Wonder Tour as we continue bringing laughter to new cities.

Support the show

https://www.patreon.com/c/DiscombobulatedwithBobbyJaycox