Best Sam Cherry Podcasts (2025)

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Coping with Seasonal Astrology Disorder w JC Mendoza Sam Santos | 193 | On The Gate 1:03:26

Play Pause

1d ago1:03:26

1:03:26

The vibes are at an all-time high on this family holiday episode! We’re joined by the hilarious JC Mendoza and Sam Santos (aka PeachfuzzPapi and soon to be PeachfuzzMami) to cover everything from Geo’s transformation goals to the great Dave Chappelle debate. The crew dives deep into Derek’s mid-life crisis, why Sam and Derek are officially "homegir…

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“What’s Our Website?” w/ Finn Wolfhard 1:20:27

3d ago1:20:27

1:20:27

Watch this show on Youtube! Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and TikTok. Advertise on What's Our Podcast? via Gumball.fm. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.…

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Sean "Diddy" Combs BPD Vigilantes | Wolfgang Hunter, Myles Toe | 192 | On The Gate 1:01:33

9d ago1:01:33

1:01:33

Wolfgang Hunter and Myles Toe transferred to the block for a heavy-hitting On The Gate! From breaking down the Diddy documentary to Wolfgang’s legendary Katt Williams impression and the reality of being a "modern-day Uncle Ruckus," the energy is high and the takes are questionable. ON THE GATE! ENJOY! Original air date: 12.15.25 Join the live chat …

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Tony Hawk 1:12:39

10d ago1:12:39

1:12:39

Are we high or is Tony Hawk actually HERE??? Or maybe he’s HIGH cuz he’s in the air on his cool skateboard!!!? Anyway, he came to the studio and then told us about breaking his femur and also how much he likes being a granddad :) P.S. Go Padres Watch this show on Youtube! Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Hea…

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Wedding Crashers and Beating Up Tupac w. Talent Harris Jr | 191 | On The Gate 1:02:50

15d ago1:02:50

1:02:50

Geo and Derek are back to unleash pure chaos with Talent! We're tackling everything from celebrity conspiracies to the practical—and often hilarious—realities of modern body modifications. Plus, a Casa de Alofoke recap! ON THE GATE! ENJOY! Original air date: 12.8.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on …

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Zach Cherry 1:26:01

17d ago1:26:01

1:26:01

Please welcome our first ever Rocco guest, Zach Cherry! Zach wanted to take a look back at the first 15 episodes of the show and of course we said yes. So join us for the inaugural What’s Our Podcast retrospective, where we answer all your (Zach’s) burning questions and take all your (Zach’s) feedback as we roll into the next chapter of the show. W…

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Long Term Effects of Being a Junkie w Aaron Putnam Priya Blunts | 190 | On The Gate 1:01:48

23d ago1:01:48

1:01:48

We're joined by the hilarious Aaron Putnam and Priya Blunts to break down some of the wildest stories—including a dive into addiction, stealing pills from family, ex-con dates, and the time Priya got hopelessly lost on Bourbon Street without a phone! Plus, we discuss Dominican racism, male comics asking for "favors," and the weird nostalgia of drug…

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Kevin Nealon 1:12:22

24d ago1:12:22

1:12:22

We’re back with the legend Kevin Nealon to talk about our mutual alma mater (SNL) and how clutch it is when you’re working at the mall as Santa and a kid pees on you but you’re wearing water-repellent Santa pants (just in time for the holiday season). Tune IN! Sign the Take A Hike Definition Petition at takeahikepetition.org! Watch this show on You…

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Episode 4: Confidentiality and Off-Market Sales 11:38

26d ago11:38

11:38

🎙️ Should you name your business when you sell — or keep it under wraps? Damien Fahey and Sam Cherry unpack confidentiality, legacy, and when an open sale makes sense. Key takeaways: 🔹 Most Tabak sales are confidential — handled via anonymous listings, NDAs, and carefully screened buyers. 🔹 Why stay confidential? Protect staff morale, reduce compet…

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Nick Mullen Nick Rochefort Mike Figs Skankfest 2025 | 189 | On The Gate 49:30

1M ago49:30

49:30

Two Nicks—Nick Mullen and Nick Rochefort — join Geo Perez and Mike Figs for a hilarious and unhinged episode recorded at Skankfest New Orleans 2025! From speculating about the intricacies of the Mexican Revolution and the absurdity of controlled protests to recounting bizarre personal stories like getting food stamps as a "bit," this episode leaves…

1
Prison Workout for Guardian Angels | Derek Humphrey | 188 | On The Gate 1:00:53

1M ago1:00:53

1:00:53

Derek Humphrey explains NYC policy changes with Derek Drescher and Geo Perez. They also discuss the pros and cons of being in prison, childhood stories before technology, achieving fame, and fighting. ON THE GATE! ENJOY! Original air date: 11.17.25 Join the live chat Wednesday nights at 11pm EST. Uncensored versions of the show streamed Monday and …

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Kate Berlant 1:27:04

1M ago1:27:04

1:27:04

Sup sickos? >:) This week, the devilish Kate Berlant is here to talk about stuff you WON’T want to tell your dad. Plus, we get to meet Beck’s butler Froderick! >:) So dive in and let the sinning begin >:) Watch this show on Youtube! Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headgum podcast. Follow Headgum on Twitter,…

1
Knowing When To Turn Yourself In | Jessica Levin Billy Hockman | 187 | On The Gate 58:12

1M ago58:12

58:12

Sometimes the only way to get help is to force it on yourself. Derek and Geo talk about times they knew they were toast. Comedians Jessica Levin and Billy Hockman share their experiences as New Jersey degenerates. ON THE GATE! ENJOY! Original air date: 11.10.25 Watch Jess' special "Party Boy" on YouTube https://www.youtube.com/watch?v=B7gxCjuM1cc J…

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Tim Heidecker 1:15:28

1M ago1:15:28

1:15:28

Tim came on the show and made us question every career move we’ve ever made. Always a pleasure, Tim! Watch this show on Youtube! Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and TikTok. Advertise on What's Our Podcast? via Gumball.fm. See Privacy Policy at https://a…

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Preparing for Parole Hearing | Taj Osorio | 186 | On The Gate 57:45

2M ago57:45

57:45

Geo Perez is in trouble! Derek Drescher is angry. Taj Osorio plays both sides. Everyone looks at Sydney Sweeney. ON THE GATE! ENJOY! Original air date: 11.3.25 Join the live chat Wednesday nights at 9pm EST. Uncensored versions of the show streamed Monday and Thursday at 2pm EST on GaSDigital.com. Signup with code OTG for the archive of the show an…

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Skyler Gisondo 1:20:27

2M ago1:20:27

1:20:27

Can’t BELIEVE we got THE Jimmy Olsen in the studio this week and he came with not 1, not 2, but 11 different ideas for what we should make our podcast be about. Seems like we landed on the best one, but also don’t know if any of this matters! Watch this show on Youtube! Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headg…

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Episode 3: Mistakes Sellers Make and How to Avoid Them 17:16

2M ago17:16

17:16

🎙️ Selling soon? In this episode, Damien Fahey and Sam Cherry share the biggest pitfalls they see from business owners — and what to do instead. Key takeaways: 🔹 Timing — there’s never a perfect moment, but hesitation can cost you. 🔹 Momentum — keep driving your business right through the sale process. 🔹 Valuation — beware of inflated numbers and p…

1
Confession of a Federal Ex w. Myles Toe Jared Schwartz | On The Gate | Ep. 185 1:04:50

2M ago1:04:50

1:04:50

We have a DASTARDLY confession on the pod today! Derek and Geo are joined in the cell with Myles Toe & Jared Schwartz to discuss REVENGE, glowing up after trauma, being dumped, the benefits of SNAP and capitalism, punching up prank ideas and much more. ON THE GATE! ENJOY! Original air date: 10.27.25 Join the live chat Wednesday nights at 11pm EST. …

1
Matt Rogers 1:28:55

2M ago1:28:55

1:28:55

Strap the heck in, we’re jumpin off an airplane with #1 bad boy Matt Rogers. Oh… and we stop to make a lil podcast along the way. Let’s hope we land this sucker safely! Watch this show on Youtube! Follow Matt on Instagram and Tiktok, and buy tickets for his Christmas in December tour here. Follow Beck on Instagram. Follow Kyle on Instagram and Twit…

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Cherry Breakin w. Brandon Trusso Brian McKenna | Ep. 184 | On The Gate 1:00:34

2M ago1:00:34

1:00:34

This week we have Brandon Trusso & Brian McKenna! They talk about the YN Geo loves, detox realizations, Derek's time in the Philippines, Brian's connections to law breakers and much more. ON THE GATE! ENJOY! Original air date: 10.20.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code …

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Sam Fragoso 1:07:19

2M ago1:07:19

1:07:19

We tried to ask Sam insightful questions about himself but he kinda ended up asking more insightful questions about the two of us. It was nice getting to know him, and, in a way, each other. Watch this show on Youtube! Listen to Sam's podcast, Talk Easy, on Apple and Spotify, and follow him on Instagram. Follow Beck on Instagram. Follow Kyle on Ins…

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My Meat My Cave w. Jared Waters Amanda Gail | Ep. 183 | On The Gate 1:01:01

2M ago1:01:01

1:01:01

This week we have Jared Waters and Amanda Gail! They talk about Amanda's love life, a female perspective on Derek's situation, the New York City Comedy scene and much more. ON THE GATE! ENJOY! Original air date: 10.13.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a disco…

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Meg Stalter 1:23:39

2M ago1:23:39

1:23:39

There’s nothing better than sitting around and talking about fashion with your boys, and that’s exactly what the Fashion Boys podcast is all about. Tune in to hear our first Fashion Boys episode (of many) with our favorite fashionable guest, Meg Stalter. Watch this show on Youtube! Follow Meg on Instagram and TikTok. Follow Beck on Instagram. Follo…

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Ropes & Dribbles w Jarrett Campbell Marito Lopez Ethan Mead | Ep. 182 | On The Gate 1:01:34

3M ago1:01:34

1:01:34

This week we have Canadians Jarrett Campbell and Marito Lopez, then our classic NY white boy Ethan Mead! They talk about getting fit, playin ball, Yankees and Toronto Blue Jays, Geo's bootyhole violations and much more. ON THE GATE! ENJOY! Original air date: 10.6.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on …

1
Jack Black 1:11:29

3M ago1:11:29

1:11:29

We talked to Jack Black! That’s crazy!!! He hung out for a couple of hours and made a brand new podcast with us. And hey, we ain’t complaining! Watch this show on Youtube! Follow Jack on Instagram and TikTok. Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. …

1
My Psych Floor Celly w. Derek & Geo | Ep. 181 | On The Gate 58:37

3M ago58:37

58:37

THE SHOW MUST GO ON! This week Derek and Geo talk about staying together for the IMPROVED podcast, mental health work while incarcerated, Derek's emotions, Geo's prostate and much more. ON THE GATE! ENJOY! Original air date: 9.29.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG…

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Brittany Broski 1:05:18

3M ago1:05:18

1:05:18

Gather round… dim the lights… Brittany’s idea for our podcast just might give you the frights……No we’re just messing around, it’s just a regular “spirited” episode with our “ghoul” new friend Brittany! Watch this show on Youtube! Follow Brittany on Instagram and TikTok. Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headg…

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Episode 2: Busting the Biggest Myths in Business Sales 19:39

3M ago19:39

19:39

In this episode Damien Fahey and Sam Cherry bust the biggest misconceptions they hear from business owners — drawing on decades of real business sales experience. Myths busted: 🔹 Multiples are straightforward – anyone can calculate them. 🔹 Brokers make easy money. 🔹 Multi-offers are the norm. 🔹 Market averages tell the full story. Real stories, str…

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The Breakup Episode w. Mike Figs JC Mendoza | Ep. 180 | On The Gate 1:01:46

3M ago1:01:46

1:01:46

This week we have Mike Figs and JC Mendoza. They talk about the state of the show, breakups, special treatment in jail, emotions and much more. ON THE GATE! ENJOY! Original air date: 9.22.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your membership. Watch …

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Brennan Lee Mulligan 1:02:34

3M ago1:02:34

1:02:34

We had NO idea what idea Brennan would bring us and we had NO idea what his idea even meant. But we learned a lot and we laughed a lot and, hey - that’s what it’s all about. Watch this show on Youtube! Follow Brennan on Instagram. Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headgum podcast. Follow Headgum on Twitter, I…

1
S04E11 - Balls and More Balls to Picasso - Part 2 1:06:51

3M ago1:06:51

1:06:51

This week, your voyagers continue their trip into Bruce Dickinson's solo discography with their second part exploring Balls to Picasso and its recent reimagining, the imaginatively titled More Balls to Picasso. Join them as they dive in to the material proper this time, both in its original and gussied up 2025 forms, along with some other nonsense.…

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Double Daddy Court w. Jessica Levin Napoleon Emill | Ep. 179 | On The Gate 1:13:24

3M ago1:13:24

1:13:24

This week we have Jessica Levin and Napoleon Emill! They talk about Star Trek, roasting each other parents, acid trips, Spike Lee joints and much more. ON THE GATE! ENJOY! Original air date: 9.15.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your membership…

1
Bobby Moynihan 1:15:00

3M ago1:15:00

1:15:00

Our old coworker Bobby comes to the show with a brand new attitude. We get into it with him, but in the end… it’s all love? Watch this show on Youtube! Follow Bobby on Instagram. Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on What's Our Podcas…

1
Credentials for the Hole w Dave Temple Big T | Ep. 178 | On The Gate 1:03:22

4M ago1:03:22

1:03:22

This week we have Dave Temple and Big T! 3 homeowners, 3 fathers, 3 recovering drug addicts. Guess who is who! Man talk about repairing things, manual labor jobs, sex, and iShowSpeed performing at The Stand. ON THE GATE! ENJOY! Original air date: 9.8.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.co…

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Claudia O'Doherty 1:02:20

4M ago1:02:20

1:02:20

Claudia O’Doherty is from Australia, but she thinks our podcast should be about the most American thing of all. Might sound crazy, but it’s actually pretty jeanius. Watch this show on Youtube! Follow Claudia on Instagram. Follow Beck on Instagram and Twitter. Follow Kyle on Instagram and Twitter. This is a Headgum podcast. Follow Headgum on Twitter…

1
Episode 1: We’re Back with Double the Brokers and Double the Insights 2:59

4M ago2:59

2:59

🎙️ Season 2 of the Tabak Business Sales Podcast is here – and it’s bigger than ever. Damien Fahey and Sam Cherry are back, joined by two new brokers, Will Ross and Sami Chesterton. In this short 3-minute kickoff episode, Will and Sami introduce themselves and share what they’re bringing to the table this season. 🎧 Whether you’re preparing to sell, …

1
S04E10 - Balls and More Balls to Picasso - Part 1 1:01:22

4M ago1:01:22

1:01:22

With its recent reimagined re-release, it seemed only fitting that Bledd and Sam take a look at Bruce Dickinson's idiosyncratic second album, Balls To Picasso. Join the Maiden Voyagers in the first of this two part side-quest as they look at the album's troubled development and discuss the two other albums that could have been! -- Enjoy the show? J…

1
The Lost Causes w Myles Toe Lawrence Reese | Ep. 177 | On The Gate 1:01:36

4M ago1:01:36

1:01:36

This week we have Myles Toe and Lawrence Reese! They talk about Derek almost burning down his apartment, Myles and Lawrence at a parade, the English language and much more. ON THE GATE! ENJOY! Air Date 9.1.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your …

1
Tim Baltz 1:14:39

4M ago1:14:39

1:14:39

We’re learning a lot about what our podcast should be about. Today, we asked Tim Baltz what he thinks and his answer took us on a journey around the world! Watch this show on Youtube! Follow Tim on Instagram. Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. …

1
Fitted Sorting Cap w Daniel J Perafan James Pontillo | Ep 176 | On The Gate 1:09:47

4M ago1:09:47

1:09:47

This week we have Daniel J Perafan and James Pontillo! They talk about addiction in the comedy community, slanging products, minorities and much more. ON THE GATE! ENJOY! Original air date: 8.25.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your membership.…

1
Marc Maron 59:31

4M ago59:31

59:31

We couldn’t really keep going with the show without stopping to ask the Big King Daddy of Podcasting if he knows what our podcast should be about. He had a lot of thoughts…… Hope he’s proud of how it turned out and thinks we have a new hit podcast! Watch this show on Youtube! Follow Marc on Instagram and Twitter and check out his new special Panick…

1
Fran Gillespie 1:00:54

4M ago1:00:54

1:00:54

Wow, our very first episode. We decided to ease into it by asking our longtime friend and collaborator Fran Gillespie to come on and see if she knows what our podcast should be about. Hope you guys like it. Watch this show on Youtube! Follow Fran on Instagram. Follow Beck on Instagram. Follow Kyle on Instagram and Twitter. This is a Headgum podcast…

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S04E09 - Run Back to the Beginning of Your Lives 1:38:33

4M ago1:38:33

1:38:33

Is it just me or does it feel like this season is lasting forever? But hey, after another impromptu break for unexplained reasons (blame life), we are back to provide your regularly scheduled Iron Maiden-themed idiocy. Well, sort of..! This week, Bledd and Sam recount their pilgrimage down to That London to catch the lads play one hell of a homecom…

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Grape Light w. Liam Dalton Aaron McCann Natalie DeCicco | Ep. 175 | On The Gate 1:03:09

4M ago1:03:09

1:03:09

This week we have Aaron McCann and Liam Dalton! They talk about struggling with addiction, relapsing, Derek getting angry and much more. ON THE GATE! ENJOY! Original air date: 8.18.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your membership. Watch the fre…

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Introducing: What's Our Podcast? with Beck Bennett and Kyle Mooney 0:50

4M ago0:50

0:50

Beck Bennett and Kyle Mooney (Saturday Night Live, former roommates) started a podcast. Except, they don’t know what their podcast should be about. Maybe their guests do? Worth a shot. Let’s see if they ever find out. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.…

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Dry Wet Dry w. Natalie DeCicco | Ep. 173 | On The Gate 1:01:38

5M ago1:01:38

1:01:38

This week we have producer Natalie DeCicco! They talk about Dereks recent viral fights, controversial white women, Natalie's lesbian lore and much more. ON THE GATE! ENJOY! Original air date: 8.4.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your membership…

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Dumb Dad Gastrology w. Dave Temple Natalie Decicco | Ep. 172 | On The Gate 1:12:53

5M ago1:12:53

1:12:53

This week we have Dave Temple and Natalie Decicco! They talk about cheating timelines, celly love/hate, MLB The Show and much more. ON THE GATE! ENJOY! Original air date: 7.28.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your membership. Watch the free liv…

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Position of Powder w. Lawrence Reese Big T | Ep. 171 | On The Gate 1:11:15

5M ago1:11:15

1:11:15

This week we have Lawrence Reese Big T! They talk about prison cinema, the hotness of Presidential wives/husbands, hot moms and much more. ON THE GATE! ENJOY! Original air date: 7.14.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your membership. Watch the f…

1
S04E08 - Blaze Bayley on Silicon Messiah and more 1:11:36

5M ago1:11:36

1:11:36

Let's rewind the clock a bit. We've covered Brave New World already - but in the immediate aftermath of Bruce Dickinson's return to Iron Maiden, what happened to Blaze Bayley? Well, who better to tell us than the man himself. Determined to forge onwards, Blaze immediately got to work putting together his solo debut, Silicon Messiah. A slab of heavy…

1
Diddy Bop with Derek Humphrey & Tristan Bowling | Ep 170 | On The Gate 1:02:41

6M ago1:02:41

1:02:41

This week we have Derek Humphrey & Tristan Bowling! They talk about neighborhoods of New York City, being homeless, MLB The Show, fighting words and much more. ON THE GATE! ENJOY! Original air date: 7.7.25 WATCH THE LIVESTREAM 2 PM EST MONDAYS and EXCLUSIVE EPISODES 2 PM EST THURSDAYS on gasdigital.com. Use promo code OTG for a discount on your mem…