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!