The Shallow End

What do a legendary bank robber in disguise and a backyard “experiment” gone catastrophically wrong have in common? They both belong squarely in The Shallow End. In Episode 205, the boys dive into the unbelievable true story of Peggy Jo Tallas—better known as “Cowboy Bob”—a free-spirited Texas woman who reinvented herself as a bearded outlaw and pulled off a string of bank robberies so smooth they baffled even seasoned FBI investigators. But beneath the disguises and daring escapes lies a deeper story about restlessness, identity, and the dangers of a life that feels too small. Then, in a sharp turn toward the absurd (and painfully unforgettable), we head to Salina, Kansas, where one man’s curiosity leads to a question no one should ever ask: what happens if you shoot a live bullet… with a pellet gun? The answer is exactly as bad as you’re imagining—and somehow worse. Plus, a listener email that proves kids, treehouses, and plastic grocery bags should never mix—and why some life lessons only come after gravity gets involved. If you love true crime, bizarre history, dumb criminal behavior, and stories that make you laugh while instinctively crossing your legs, this episode is for you. In this episode: The shocking true identity of “Cowboy Bob” One of the strangest bank robbery careers in Texas history A DIY science experiment that went disastrously wrong Listener story: A childhood stunt that almost worked… until it didn’t Pour yourself something strong and remember: curiosity may fuel innovation—but sometimes it just lands you in the ER. Learn more about your ad choices. Visit megaphone.fm/adchoices

What do a counterfeit cash scheme, a Target return counter, and a doomed diamond heist have in common? Absolutely terrible decision-making—and that’s exactly what’s waiting for you in this episode of The Shallow End. JG and Lindsay dive headfirst into two wildly absurd true crime stories that prove sometimes the biggest threat to criminals… is themselves. First, a man in Augusta, Georgia attempts to return a printer—only to accidentally leave behind sheets of freshly printed counterfeit money inside. What follows is a slow-motion unraveling of one of the least thought-out crimes imaginable, all thanks to a diligent retail employee and one very talkative machine. Then, things somehow get even worse. Meet Leroy and Marcy, two aspiring jewel thieves whose meticulously unmeticulously planned heist ends with smashed glass, a panicked escape, and a fateful elevator ride straight into disaster. With stolen diamond rings, a broken getaway plan, and one unforgettable attempt to hide evidence (yes… inside a human body), this story spirals into one of the most spectacularly botched robberies you’ll ever hear. Along the way, the team shares outrageous customer service horror stories—including attempted double refunds, questionable return logic, and the kind of retail chaos that makes you wonder how humanity functions at all. This episode is packed with laugh-out-loud moments, unbelievable true stories, and a reminder that crime doesn’t pay… especially when you forget the evidence in the printer. In this episode: A counterfeit operation undone by a simple return A jewelry heist foiled by… an elevator Real-life retail stories that defy logic Dumb decisions, instant consequences, and comedy gold If you love hilarious true crime, ridiculous criminals, and stories that make you feel just a little bit smarter by comparison, this episode is for you. Listen now—and remember: make good choices… your life might depend on it. Learn more about your ad choices. Visit megaphone.fm/adchoices

Because even chaos takes a holiday… It’s a Shallow End classic. Due to Easter weekend, we’re cracking open the vault and re-releasing one of our all-time favorite episodes—and trust us, it’s worth resurrecting. JG dives headfirst (as one does) into the spectacularly ridiculous sinking of a World War II Nazi U-Boat—because sometimes history isn’t just tragic… It’s unintentionally hilarious. Meanwhile, Lindsay asks an important question that absolutely no one should be qualified to answer: Can you coach a Little League team all the way to the World Series… and still find time to rob 13 banks? (Spoiler: apparently, yes.) It’s incompetence, ambition, bad decisions, and baffling life choices—all wrapped up in one beautifully broken episode. If any defects in this episode are discovered, do not attempt to repair them yourself. Please return to an authorized Shallow End service center… or just laugh and let it happen. Learn more about your ad choices. Visit megaphone.fm/adchoices

What happens when criminals make every possible wrong decision… and then double down? In this episode of The Shallow End, we dive headfirst into a series of real-life stories that prove you don’t need a mastermind to commit a crime—sometimes all you need is spectacularly bad judgment. First, meet Darren Kimpton—a burglar having what can only be described as an aggressively terrible day. After botching one break-in and leaving behind a literal trail of blood (yes, DNA included), he decides the logical next step is… to try again. What follows is less of a crime and more of a live-action surrender. Then, things shift from clumsy crime to courtroom chaos. A woman named Kimberly Carroll attempts to attend a virtual court hearing via Zoom—while driving. What unfolds is a painfully awkward, wildly viral moment involving a skeptical judge, a very obvious lie, and one of the most expensive car rides imaginable. Plus, listener stories that will make you question how anyone boards the wrong plane—and doesn’t realize it until takeoff. This episode is packed with: Dumb criminal fails (the kind that practically solve themselves) Viral courtroom moments you have to hear to believe Absurd real-life stories that feel scripted… but aren’t The kind of humor that makes you grateful you’re not that person If you love true crime with a comedic twist, unbelievable real-life mishaps, and stories where everything goes wrong in the most entertaining way possible—welcome to The Shallow End. Learn more about your ad choices. Visit megaphone.fm/adchoices

What starts as a routine flight out of Mogadishu turns into one of the strangest “instant karma” stories you’ll ever hear… when a man in a wheelchair boards a plane with a deadly secret—and what happens next defies every expectation. This is a true story of chaos, survival, and a twist so unbelievable it sounds fictional… but isn’t. Then, we head to Clearwater, Florida—because of course we do—where a karaoke night goes completely off the rails. One man waits patiently for his moment in the spotlight… until a broken karaoke machine pushes him into a decision that lands him in handcuffs instead of the chorus. Plus: a listener story featuring a literal “Rick Roll” (gravity-assisted), and a reminder that sometimes the most dangerous place on Earth… is an open mic night. In this episode: A real-life airplane bombing attempt with a bizarre outcome A Florida karaoke meltdown involving a gun (yes, really) Listener humiliation at a Rick Astley concert The fine line between performance art and public disaster If you love true dumb criminal stories, unbelievable real-life events, and dark humor with a twist of “what did I just hear?”—welcome back to The Shallow End. Learn more about your ad choices. Visit megaphone.fm/adchoices