If This Doesn’t Work…

Comedian David Jones has been kicked off a plane, survived some unbelievable drunken nights, and worked in an industry everyone loves to hate. But somehow, it was texting his ex that made him seriously reconsider drinking. David joins Justin Anderson and Mike Caropreso on *If This Doesn't Work…* for a ridiculous conversation about stand-up comedy, addiction, bad decisions, growing up in Maryla...

Comedian Umar Khan returns to If This Doesn't Work… after two years of touring, performing with some of comedy's biggest names, and figuring out what actually matters in life. Umar talks about traveling through Australia and New Zealand with Mark Normand, his early days alongside Stavros Halkias, working with Tim Dillon, and why chasing success in comedy isn't always what it's crac...

Baltimore rapper Menace Monroe says the streets didn’t choose him, he chose them. After entering the juvenile system as a kid, serving multiple prison sentences and coming home again this year, Menace is trying to build a life that doesn’t end with another bid. Menace joins Justin to discuss becoming addicted to criminal life before drugs, being incarcerated alongside his brother, facing 63 charge...

Jeff “Chippy” Taylor Jr. came in ready to talk about change and ended up telling a much bigger story. At his heaviest, Chippy was 465 pounds. He lost more than 100 pounds, found running, battled depression and anxiety, checked himself into a psychiatric hospital, went through broken relationships and family trauma, landed in jail after a fight in Federal Hill, and eventually found himself rebuildi...

Bam Jacobs won McGooby’s New Comedian of the Year. Dom Solesky got second and seems to be processing it beautifully. Bam and Dom return to talk about comedy competitions, Dom’s JFL audition, disastrous New York trips, bombing in the wrong room, the delusion required to keep doing stand-up, public freakouts, terrible customer service, and their upcoming short film Easy Money. Along the way, Bam adm...

Check Out the Website: https://if-this-doesnt-work.pages.dev/Justin and Mike are back for a two-man episode that starts with one surprisingly serious question: why is saying “I love you” so much harder than just saying “love you”?Then everything falls apart. This week we're digging into the Ig Nobel Prizes, frozen poop knives, cockroach milk, military dolphins, zebra-striped cows, a 103-year-o...

Mo Noor is back, and somehow this turns into therapy again. We get into men’s groups, why chaos can feel normal, comedy, relationships, weird childhood memories, cult-ish behavior, sexual awakenings, and the kind of personal shit that probably wasn’t supposed to come up on a podcast. Mo also talks about getting back to making his own stuff, including his micro-podcast and comedy clips. Follow Mo N...

Justin went to Las Vegas and sat down with 607 Unc for another conversation that immediately went somewhere nobody could have predicted. Unc talks about the Wack 100 confrontation, his relationship with Charleston White, why internet “content” can become genuinely dangerous, why he considers marriage and streaming different kinds of prison, and his theories about animals, human bodies, relationshi...

Melvin Daniels went from being one of Federal Hill’s most dedicated customers to owning Mugshots, Locals Only and Wanna Smash. He explains how he opened a bar with no industry experience, why Mugshots found an audience other bars were overlooking, and how its success changed the business around it. Melvin joins Justin and Najee to talk about hiring bartenders for personality and social pull, race...

Before Nick Troisi ever became the vocalist of Omen Skye, he spent years living what he calls the “rock-star lifestyle” without actually having the band. He joins Justin and Mike to talk about addiction, getting sober, learning to scream in his car and finally using the musical potential he thought he had wasted. Nick takes us through the whole path: getting cut from Chesapeake JV football, receiv...

Justin came back from six days hiking Iceland with roughly 50 pounds on his back, a damaged knee and one important realization: he might not actually be a hiker. Justin’s cousin Chris Carroll joins Mike and Justin to talk about Iceland’s volcanic terrain, sulfur clouds, crowded hiking huts, fermented shark, Sky Lagoon and the 17-mile push that finally ended the trip. Then the conversation turns to...

Mike Nauton found a man unconscious in a gas-station parking lot and somehow a Yoo-hoo became part of the story. A longtime friend joins Justin and Mike to talk about growing up as a neighborhood knucklehead, becoming a father and provider, working in the cell-tower industry, unexpected encounters in Houston, questioning his own political beliefs, and using AI to examine the evidence. Subscribe fo...

KC (Kasey) joins Justin to tell the full nightmare-room story, explain how an acid-fueled house party led to a raid and cocaine charges she says were eventually dismissed, and confess the Air Force incident she believes should have gotten her kicked out. They also get into parenting anxiety, cleaning houses, comedy jealousy, addiction, questionable childhood decisions and the seven-second gravity...

King Yella joins Justin Anderson in Las Vegas for a raw conversation about getting baptized, feeling like a dark cloud had followed him from the streets, and finally taking steps to change his life. He speaks about trauma and self-medication, turning down a drink for the first time, prison, fatherhood, the message behind drill music, Lil Durk and Pooh Shiesty’s situations, why content creation has...

607 Unc came through and turned the podcast into a broken TV signal from another timeline. We talked about downloads, timelines, gut-brain theories, food programming, linen sheets, dreams, attention, YSL vs OTF, Crip Mac, Adam22, piss therapy, love, death, and whether any of us actually exist. This is one of the wildest conversations we’ve ever had. Watch the full interview and let us know the exa...

Comedian Karan Singh joins Justin for one of those episodes that starts with a name pronunciation and somehow ends up in Virginia Tech crime stories, Kash Patel impressions, plastic surgery office chaos, dating apps, bad jobs, local comedy, family expectations, and possibly the meanest grandma story ever told on the show. Karan talks about going from “K Squizzy” to his real name, growing up in Nor...

Steve Huber of 100.7 The Bay joins If This Doesn’t Work… for a long, honest conversation about Baltimore radio, growing up on a farm, starting at 98 Rock as an intern, becoming a music director, moving to 100.7 The Bay, and what happens when the station you helped build gets sold. Huber talks about the current situation at 100.7 The Bay, how the staff found out, what the final stretch feels like,...

Skyy Royal is back on If This Doesn’t Work… and somehow this episode starts with grief, turns into a conversation about spiritual massage, and ends up somewhere between the Matrix, Bigfoot, aliens, meat being dead bodies, and whether the world is a “dimensional threshold.”Skyy talks about losing his dog Fluffy, how he sees grief differently now, the coma experience that made him feel like he saw t...

Comedian Matt Pennington returns to If This Doesn’t Work… for a conversation that somehow moves from internet arguments and dispensary customers to childhood Adderall, getting arrested with mushrooms, cocaine heart-rate experiments, fear of looking cringey, and one of the best period-sex analogies ever told. Matt talks about working at a dispensary, why “sativa versus indica” does not tell the who...

Comedian Mert Wolf joins If This Doesn’t Work… for a conversation that starts with whether his mom would help with a drug deal and somehow gets stranger from there. Mert talks about growing up in Turkey, moving to America, legally choosing the last name Wolf, accidentally calling 911 during an argument, being haunted in Columbia, Turkish circumcision ceremonies, kidney stones, conspiracy theories,...

We still can’t believe this happened. On May 8th, we got to sit down with comedian Steve Hofstetter in the greenroom at Baltimore Soundstage before his show. Steve was insanely generous with his time, and the whole thing felt surreal; walking backstage, sitting behind the curtain, and getting a real conversation with someone who has been doing comedy at a level most people never reach. We talked a...

Comedian Luca Spinoso joins If This Doesn’t Work… for one of the wildest episodes we’ve had in a while. Luca talks about growing up between Florida and Maryland, his chaotic childhood, the stepmom from hell, getting stabbed while working as a bouncer, battling addiction, getting sober, becoming a husband, finding out he might be a dad, and somehow ending up in Baltimore comedy. He also tells the i...

This week on If This Doesn’t Work… we handed the microphone to our friend’s 9-year-old daughter and let her answer the kind of questions most adults can’t even handle. What followed was part Kids Say the Darndest Things, part tiny roast battle, part accidental philosophy seminar. Harleigh explains why adults make no sense, why dogs are probably faking it, what she’d do if she ruled the world, how...

Baltimore-area comedian Caitlin Austin joins If This Doesn’t Work… for one of the strangest, funniest, and weirdly heartfelt episodes we’ve done yet. Caitlin talks about growing up around Dundalk chaos, being raised by her grandmother, having a real-life “prison papa,” becoming a pre-K teacher, getting sober, starting stand-up comedy, living in her car while still going to open mics, smoking Newpo...

Baltimore graffiti legends DLordInk and Meca came through If This Doesn’t Work to talk about the real culture behind graffiti; the rules, the respect, the beef, the crews, the toys, the side-busting, and how street art turns into paid murals across the country. In this episode, Danny Lorden aka DLordInk and Meca break down what most people don’t understand about graffiti: how writers earn respect,...