2 Broke Boys

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:

Videographer Banga Jaxon stopped by If This Doesn’t Work… to talk about what it’s really like shooting music videos in Philly, Baltimore, and Delaware. From chaotic rap shoots, dangerous situations, fake money, contracts, and late-night calls, to working with bigger names, staying neutral in the scene, and why authenticity matters more than fame. This one goes all over the place in the best way.We also get into how Banga got started, why he moved from rapping into videography, the difference between a cheap video and a big-budget one, the weirdest concepts he’s been asked to shoot, mental health, therapy, and somehow NSYNC, Eminem, and screamo all end up in the conversation too.If you like behind-the-scenes music industry stories, real talk, and funny chaos, this episode is for you.Check out Banga:Instagram: https://www.instagram.com/therealbangajaxon/Follow the Podcast:

Dom Solesky returns to If This Doesn’t Work… to talk about going viral, getting recognized in public, landing brand deals, getting management with Brillstein, and preparing for a Just for Laughs New Faces audition in New York. The conversation also gets into comedy, content strategy, creator money, construction work, Baltimore media, sports betting, and a lot of wild side roads along the way.Do yourself a favor and go see Dom live.Follow Dom:

Jean-Marie Rose Pfeifer joins If This Doesn’t Work… for one of the wildest life stories we’ve heard on the podcast.We talk about addiction, jail, recovery, rebuilding her life, plant medicine, trauma, somatic healing, skydiving, and how she went from absolute chaos to owning a skydiving company and two airplanes.Jean-Marie also opens up about chasing an image of success, leaving New York behind, writing her memoir, and the spiritual work that changed how she sees herself and her future.If you like real conversations about recovery, transformation, healing, mindset, and unconventional life paths, this episode is for you.Follow Jean-Marie Rose Pfeifer:Instagram: https://www.instagram.com/jeanmarierosepfeifer/Check out Skydive Chesapeake:https://skydivechesapeake.com/Subscribe for more episodes of If This Doesn’t Work…

Davey Cook from True Colors Beauty Co stopped by If This Doesn’t Work for a conversation that went way deeper than beauty and business. We got into addiction recovery, grief, family, entrepreneurship, authenticity, confidence, and what it really takes to rebuild yourself while trying to create something meaningful.Davey opens up about getting clean, losing his mom, growing up around chaos, working in a female-dominated industry, and building a brand that helps people feel like the best version of themselves. One minute it’s funny, the next it gets real fast... exactly how we like it.If you’re into real conversations about growth, pain, identity, recovery, business, and the messy road to becoming who you are, this one’s worth watching.Go Check Out Davey:Instagram: https://www.instagram.com/daveylee_mua/True Color Beauty Co: https://truecolorsbeautyco.com/True Color Beauty Co Instagram: https://www.instagram.com/truecolorsbeautyco/True Color Beauty Co Facebook: https://www.facebook.com/truecolorsbydavey/

Matt Brown joins If This Doesn’t Work… for one of our wildest episodes yet. We get into his Kill Tony experience, what it’s actually like waiting in that bucket-pull chaos, why the Austin comedy scene wasn’t for him, and why he thinks most comics need to be bullied a little more.We also get into some much darker territory: losing both parents to cancer, addiction, acting out in high school, baseball, getting hooked on opiates, bombing in brutal rooms, insane road stories, and how grief, comedy, and self-destruction all get tangled together.Matt is one of those comics who can go from deeply personal to completely unhinged in about two seconds, so this episode goes everywhere: Kill Tony, Tom Segura, comedy club politics, dark jokes, weird jobs, Austin vs Baltimore, and some of the most reckless riffs we’ve had on the show in a minute.Check out Matt Brown here:Instagram: https://www.instagram.com/mattbcomedy/Poe Boys Prods: https://www.instagram.com/poeboysprod/Subscribe to If This Doesn’t Work… for more long-fo

Tommy Sinbazo might be one of the most interesting guests we’ve had on If This Doesn’t Work...Baltimore comedian, musician, builder, proud geek, and the man behind the band B.U.S.S.I. sits down with us to talk about everything from Dungeons & Dragons, LARPing, and medieval combat to robot building, metal music, murder mystery shows, voiceover work, 98 Rock, and growing up in Baltimore.We get into Tommy’s wild stories from foam weapon battles and armored combat, the origin of Bionic Universal Super Soldiers Incorporated (Bussi), his comedy background, the murder mystery shows with Justin Schlegel and Eric Woodworth, and how he got into building robots, Mandalorian armor, and all kinds of insane props.This one goes all over the place in the best way possible.Go Check Out Tommy:Instagram: https://www.instagram.com/tommy_sinbazo/Facebook: https://www.facebook.com/tommy.sinbazo/LaughFinder Podcast:Spotify: https://open.spotify.com/show/4WeJAxQFOzhkutltlNVJmB?si=3d8068c32ccf4c6eApple Podcasts: https://podcasts.

Najee Thrash and Josh Grimes join If This Doesn’t Work… for a wild one that somehow covers relationship surveillance, peptides, dating gurus, UFC, Dune, Epstein files, AI, body cam footage, video games, and the absolute chaos of smelling salts.This episode goes from genuinely interesting to completely off the rails in the best possible way.If you like episodes where the conversation keeps mutating into something crazier, this one’s for you.

Justin Schlegel from 98 Rock joins us for one of the funniest episodes we’ve done.We get into his early radio grind, overnight shifts, working multiple jobs with zero sleep, and the insane format changes that had him constantly starting over in radio.Then we get into the good stuff:-Wild 98 Rock stories-how he got into stand-up comedy-moving to Los Angeles and coming back-almost losing the morning show with the “Flapjack & Pickle” prank-radio bits that blew up-comedy influences like Shane Gillis, Louis C.K., Norm Macdonald, Brian Regan, Patrice O’Neal-Baltimore radio history + behind-the-scenes chaosand a ton of ridiculous side stories that go completely off the rails (in the best way)Justin is sharp, hilarious, and a monster storyteller. This was a banger.If you like comedy podcasts, radio stories, Baltimore legends, and unfiltered conversations, this one’s for you.Drop a comment: What was your favorite Justin story from this episode?

Na’im Ali pulled up and we got into the real comedian emotional rollercoaster: bombing so hard you question your whole life… then the next week you’re on top of the world.We talk Skankfest excess, Philly vs NYC (and why NYC is basically a rat civilization), writing jokes vs “just telling stories”, getting arrested over a bench warrant, plus the most chaotic hypotheticals you’ll ever hear.You Can Find Na'im Ali: GO SEE HIM LIVE!Instagram: https://www.instagram.com/naim__ali/YouTube: https://youtube.com/@naimali3135?si=YRgjCi_2NaTl9T1NDurag and the Deertag Podcast: https://youtube.com/@duragandthedeertag?si=wcERoDgO_dH5D8LeTrue Dat Podcast: https://youtube.com/@truedatpod?si=hsF6IcYdWretwCmbDurag and the Deertag Patreon: https://patreon.com/duragandthedeertag?utm_medium=clipboard_copy&utm_source=copyLink&utm_campaign=creatorshare_fan&utm_content=join_linkGasDigital.com

Mo Noor pulls up and we immediately derail into self-care, Brazilian wax logistics, and the uncomfortable truth that everything is over-sexualized in 2026, and even “fluff the rice.”We get into:The weird politics of lotion / skincare / “serum” and why straight guys act like it’s illegalThe absolute insanity of prison pen-pal dating sites (aka “soup money”)Comedy growth: hosting, warming up a room, and why it’s a long gameModern dating vs. real-life interactions (including a laundromat meet-cute that goes off the rails)Taking the pod to the streets: humanizing homelessness and actually learning people’s namesAnd a bunch of chaotic bits you definitely shouldn’t try at homeIf you laughed even once, like + subscribe and drop a comment with your favorite moment so Mike can clip it.Follow Mo:

Roberto Reed pulls up and this episode immediately goes off the rails. From ball pain horror stories to body cam footage obsession, comedy origin stories, therapy debates, and the kind of riffs you can’t plan.We talk: starting standup at 19, dropping out of college, working at a comedy club, why fear is an underrated motivator, the weirdest ER visit ever, and how to stay grounded while chasing big goals.You Can Find Roberto:Instagram: https://www.instagram.com/robertoreed_/

Nitres Tha Veteran pulls up to If This Doesn’t Work… to talk about the real meaning of being independent, why “ownership” doesn’t matter if you have nothing worth owning, and how most artists are doing “music” but not doing business.He breaks down coming up in Raleigh, NC, the difference between old-school album culture vs today’s viral single chase, and why originality is getting watered down. We get into his 20-year journey, family roots (raised by his grandparents), discipline vs chaos in songwriting, and the new album “Switch Up” dropping March 13 We also talk about his first major industry moments (including Petey Pablo), almost signing situations, and his experience filming a Philly-based reality show “The In Crowd 215”, phones taken, tension everywhere, and the unexpected anxiety that came with it.Nitres Tha Veteran “Switch Up” drops March 13.Tap in and support independent artists the right way.You can find Nitres:Instagram: (7) InstagramTikTok: https://www.tiktok.com/@nitresthaveterantv?is_from_webapp

Comedian Chris Randolph joins If This Doesn’t Work… for an episode that somehow hits everything: comedy scene honesty, weird jobs, “pet bird” psychopath energy, conspiracy rabbit holes (Mud Flood), the scariest truth about death (it’s basically FOMO), a brutal staph infection story, and a wild Baltimore night that ended with a bathroom gunshot story.You Can Find Chris Randolph:Instagram: https://www.instagram.com/chris__randolph/on The Happy Podcast: https://youtube.com/@lukeharris5397?si=E3YWBD2aw8SezDx6The Happy Podcast on Spotify: https://open.spotify.com/show/1egTByrvxJQ8C6FmZiCsVg?si=bee92af2d17745ccFollow the Podcast:

Ray Wroten from Bond & Bentley pulls up to the studio to talk touring, local Maryland venues, why the band re-recorded fan-favorite songs instead of “remastering,” and how recording live in the room keeps the human feel intact.We also get into: ridiculous band name ideas, bar-gig requests, “Two Dollar Hot Dog / One Dollar Water,” sobriety + anxiety spirals, meditation that actually works, running a trivia company (M.R. Pub Games), and the most important hypothetical of all time: how many 10-year-olds in bike helmets could you take with a baseball bat?Bond & Bentley “Remnants” is out now.Ray also hosts trivia through M.R. Pub Games.Upcoming: Bond & Bentley live Feb 28 at The Room at Cedar Grove (Lewes, Delaware) dinner + show benefit format.You can find Ray: Website: raywrotenmusic.comFacebook: facebook.com/raywrotenmusicInstagram: instagram.com/raywrotenSpotify: open.spotify.com/artist/5CtSfmKFtZlg8R35flezgUiTunes: itunes.apple.com/us/artist/ray-wroten/412672792You can find Bond & Bentley:Webs

TMZ Baltimore (YC) pulls up to If This Doesn’t Work… to talk about building Baltimore’s biggest blog/vlog page, going viral during the pandemic, rebuilding the page 11 times, and why he switched from posting drama to posting his own life. YC also shares a heavy, real story about a laced street edible, months in the hospital, therapy, and turning that experience into his independent film “Laced” (drops January 1, 2026).We also get into WorldStar-era lessons, internet psychology (how virality really works), Baltimore getting worse over the years, and YC’s short film recommendations.Follow TMZ Baltimore/ Tap In:TMZ Baltimore (YC): IG: https://www.instagram.com/tmzbaltimore/YouTube: https://www.youtube.com/@TheMoaneyZoneTikTok: https://www.tiktok.com/@tmzbaltimore__LACED the movie: https://www.youtube.com/watch?v=o273rnduaas

Baltimore comedian Bam Jacobs pulls up for a chaotic episode: stage name origin, growing up Baltimore/Bel Air, Chuck E. Cheese stories, getting arrested for stealing chocolate milk, comedy writing vs storytelling, true crime doc obsession, and a full run of unhinged hypotheticals.In this episode:-Why he chose “Bam” (and why stage names can be corny)-Baltimore vs Bel Air + the “claiming the city” debate-Chuck E. Cheese / Panera / construction life stories-The chocolate milk arrest story (yes, really)-Favorite comics + getting better at stand-up (reps, reps, reps)-True crime docs, “Perfect Neighbor,” and the “open mic = American Idol” take-Would-you-rather / deep-ish questions that immediately go off the railsYou can find Bam:Instagram: https://www.instagram.com/bam.jacobs/Facebook: https://www.facebook.com/bam.jacobs.2025/YouTube: https://youtube.com/@bamjacobs9162?si=yTHUpTPzySWrv3PJ

If This Doesn’t Work… is back! and this one’s for the DMV.We’re joined by The Walking Flame, a rapper from Annapolis, Maryland, to talk about building a real brand, learning to record + mix at home, performing in Pittsburgh, and being open about OCD and what it took to overcome the worst years of it.We get into how visuals changed everything, why Maryland needs more venues for artists, the story behind his music grind, his projects like Flames on Wheels, and the albums Delusional + Sacrifice. We also talk about loss, motivation, and why creating matters more than ever heading into 2026.Follow / Listen / Watch The Walking Flame:YouTube: https://youtube.com/@thewalkingflame?si=LH2E5GuGQJfrV-TAInstagram: https://www.instagram.com/thewalkingflame/Apple Music: https://music.apple.com/us/artist/the-walking-flame/1607625216Spotify: https://open.spotify.com/artist/3fEG28uvnb6sMM1CcFb4UD?si=CEPrwGzBSIy0t6qEX31OdQTidal: https://tidal.com/artist/30432070TikTok: https://www.tiktok.com/@thewalkingflame?is_from_webapp=1&am

Dre 91 (Retro Since 91) pulled up and this one went everywhere. From not caring about metrics, to therapy + divorce, to why love is a higher vibration than authenticity, to “brain rot” guilty pleasures like Love After Lockup and public freakouts.We also get into Dre’s new project WAVESSS and how he builds as an artist: short tracklists, retro visuals, wrestling inspiration, and a team behind the scenes. Plus: movie talk (Rush Hour 2, Friday, Scary Movie), Marvel fatigue, and the wildest hypothetical you’ll hear today about infinite 10-year-olds with bike helmets.Check out Dre 91:IG: https://www.instagram.com/retrosince91/Latest Project: WAVESSS: https://music.apple.com/us/album/wavesss-ep/1853907132Apple Music: https://music.apple.com/us/artist/dre-91/1497822094Spotify: https://open.spotify.com/artist/0YExi90NFgCEi7V5kEqcxd?si=2Ymhu3t1S7KiMk7CdTaNaAIf you rocked with this episode, like/comment (showing love costs $0), and subscribe for more.

Standup comedian Adam Freesman joins If This Doesn’t Work… for a fully unhinged hang. We talk about how he went from a Division 1 track & field thrower to a Baltimore comic, getting guns pulled on him by literal kids, bombing at early open mics, porn-brain relationships, intrusive thoughts, Thanksgiving food hot takes, and why so much modern comedy content kinda sucks.In this episode we get into:-Growing up an athlete and going Division 1 for track & field (javelin, shot put, hammer throw)-Quitting soccer, lifting like a maniac, and how obscure Olympic sports actually work-Moving to Baltimore in 2020 and hitting his first open mic in May 2021-The brutal reality of eating shit on stage and why delusion is required to do standup-A wild story about kids stealing a moped and pulling guns on him in the city-Calling 911, doing a street ID with the cops, and imagining retaliation after-Delusional comics, lack of self-awareness, and why “my friends say I’m funny” is not a personality-The Kill Tony effect, cro