If This Doesn’t Work…

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 the framework of reality, and how massage became more than just bodywork for him. He gets into emotional release, men crying on the massage table, why so many men never experience safe touch, and why he thinks men need other men more than they realize.Then, naturally, the conversation turns into vegetarianism, human flesh theories, Bigfoot, aliens, digital ID, social control, Trump, Israel, and the one hidden truth Skyy wishes everyone knew.This one needs a part two.Follow Skyy Royal:BandCamp: siroyal.bandcamp.comSoundcloud: soundcloud.com/kinqsmoothYouTube: https://www.youtube.com/@UCR8Cs9H11iY1wWCO_ll81YQ Facebook: facebook.com/SirCieloSmoothInstagram: https://www.instagram.com/skyyroyal/Website: https://beacons.ai/skyyroyalFollow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pc

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 whole story, sitting in the front seat of a police car after being caught with mushrooms, growing up medicated for ADHD, and watching someone attempt an absolutely irresponsible amount of cocaine in a single sniff.We also get into sovereign citizens, internet rage bait, drug-fueled art, Bill Hicks, Bill Burr, Patrice O’Neal, local comedy, and why some comedians would rather post nothing than risk looking embarrassing for ten seconds.Follow Matt Pennington on social media and support live comedy in Baltimore.Instagram: https://www.instagram.com/mattpenning10/X: https://x.com/mattpenning10Threads: https://www.threads.com/@mattpenning10YouTube: @MattPenningtonTSRSubscribe to If This Doesn’t Work… for full conversations, stand-up stories, bad decisions, and occasional evidence that the internet was a mistake.Follow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pc#MattPennington #BaltimoreComedy #ComedyPodcast

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, restaurant jobs, fatherhood and whether Donald Trump might secretly be Elvis.Mert also answers the important questions: Which animal would be the most racist? How many helmeted ten-year-olds could he defeat with a baseball bat? And would he rather be cheated on or discover that his partner had a serious drug problem?Follow Mert Wolf:Instagram: @MertWolf11Upcoming shows:June 13 — The Ottobar, BaltimoreJune 19 — Pure Board Shop, AnnapolisFollow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pc

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 about cancel culture, why Steve thinks nobody has actually been “canceled,” how comedy has changed, becoming a dad after years of living child-free, the real cost of having a kid, what it takes to survive 25 years in stand-up, and the story of how he became one of Facebook’s first “whales” before social media was even really social media.Also, yes, we asked him how many helmet-wearing 10-year-olds he could fight with a baseball bat.Huge thank you to Steve Hofstetter for saying yes and being incredibly cool to us.Follow Steve Hofstetter:YouTube: https://www.youtube.com/@stevehofstetterLive Shows: stevehofstetter.com/tourdatesPatreon: patreon.com/SteveHofstetterThreads: threads.net/@stevehofstetterFacebook: facebook.com/SteveHofstetterInstagram: instagram.com/SteveHofstetterReddit: reddit.com/r/SteveHofstetterApple Music: itunes.apple.com/us/artist/steve-hofstetter/130203571Book: amazon.com/Ginger-Kid-Mostly-Tales-Former/dp/1419728709Steel City Arts Foundation: https://steelcityaf.com/Follow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pc

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 insane story of calling the cops on his “competition,” explains how Kill Tony helped get normal people into comedy, breaks down his story-based style on stage, and answers some of our dumbest questions yet. This one goes from dark to hilarious to weirdly heartfelt about every five minutes.

Follow Luca: Instagram: https://www.instagram.com/lucawoodspinoso/TikTok: @lucaspinoso1Follow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pc

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 Roblox could apparently fix homelessness, and why everyone in the room needs serious help with fashion.Then, near the end, her little brother Holden joins the show for a few minutes because after watching his sister do it, he basically said, “what about me?”This episode is chaotic, ridiculous, strangely honest, and somehow one of the funniest conversations we’ve had on the podcast.New episodes of If This Doesn’t Work… every Monday @ 9am.Subscribe for more conversations with comedians, artists, friends, weirdos, and now apparently children who are funnier than us.

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 Newport 100s, calling the cops on herself, and somehow turning all of it into comedy.This episode goes from completely unhinged to genuinely inspiring about every five minutes.Follow Caitlin Austin:Instagram: https://www.instagram.com/caitlinisacutie?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==Follow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pcNew episodes every week.

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, what makes someone a “toy,” why side-busting matters, how Baltimore’s graffiti scene has changed, and how social media made the culture bigger, easier to copy, and harder to control.They also talk about KSW, Baltimore graffiti history, painting trains, the difference between street bombing and mural work, Banksy, Jake Paul, MGK’s DC Warped Tour stage, road life, painting across America, and what it means to turn something illegal, dangerous, and underground into a real career.Next time you watch an episode, the set behind us will be painted by these two.You can find and commission art from these guys here:DLordInk: Insta: https://www.instagram.com/dlordink/Instagram Art & Merch: https://www.instagram.com/dlordink_art/Merch: https://dlordink.com/TikTok: https://www.tiktok.com/@dlordinkMeca: Insta: https://www.instagram.com/jaemeca/Follow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pc

Baltimore comedian Kwame Kumah joins If This Doesn’t Work… for a conversation that goes from completely ridiculous to surprisingly real.Kwame talks about growing up near Annapolis/Odenton, being raised by Ghanaian parents, getting influenced by his older sister’s 90s pop taste, and how his name connects to Ghanaian day-name traditions. He also gets into his finance background, reading graphs, how easy it is to manipulate data, and why he eventually walked away from the corporate world.From there, the episode goes everywhere: Afroman’s police raid and the infamous lemon pound cake, Kwame’s worst job in door-to-door roofing sales, teen court over fake weed, Catholic guilt, musicals, reality TV, aliens, DMT, simulation theory, and the impossible question of how many helmet-wearing 10-year-olds you could fight with a baseball bat.But the biggest moment comes when Kwame opens up about the pressure of working in finance, waking up crying, dealing with depression, getting help, and eventually rebuilding his life through bartending, comedy, and learning how to get through the bad stretches.Check Out Kwame:Instagram: https://www.instagram.com/kwame_kumah/TikTok: https://www.tiktok.com/@UCVHtoTno58suuc6ZYqLNu3g https://www.youtube.com/@Kwame_KumahFollow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pc

Dre aka RetroSince91 came back through If This Doesn’t Work… for a conversation about music, life, relationships, privacy, and staying true to yourself in a world that constantly pushes people to overshare, compare, and perform online.We talk about his new project Waves 2, why he leans melodic over purely technical rap, building a real community instead of chasing numbers, how divorce changed his outlook, why boundaries matter, what men should be more honest about, and why some parts of your life should stay private.Dre also previews new music during the episode, including tracks from Waves 2, and breaks down how he approaches making art that actually feels like him.Follow Dre: @RetroSince91Check out Waves 2 available today 4/20/2026Follow the Podcast:📸 Instagram: https://www.instagram.com/ifthisdoesntworkpodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==🎵 TikTok Main: https://www.tiktok.com/@thejustintimee?is_from_webapp=1&sender_device=pc🎵 TikTok Clips: https://www.tiktok.com/@itdw_clips?is_from_webapp=1&sender_device=pc