Drop A Pin

🌎 Ari Shaffir Joins Donnie & Chaps for a No-Frills Travel Deep Dive

✈️ Hostel Life: Ari shares unfiltered stories from dirt-cheap stays, including bunking with strangers, wild hostel parties, and unexpected friendships.
💸 Budget Travel Hacks: How Ari stretches a dollar on the road—sleeping in airports, hitchhiking, and eating like a local.
🏝️ Off-the-Grid Adventures: From hidden villages to under-the-radar countries, Ari talks about the best (and worst) places he's wandered into.
🤢 Sketchy Situations: A few close calls—dodging scams, weird food experiences, and the occasional "should I be here?" moments.
📚 Gettin’ Cultured w/ Nick Turani

🤔 Chaps & Donnie challenge Nick with travel trivia and odd cultural facts.
🏆 Can Nick guess the customs, taboos, or weird laws from different countries?
😂 As always, chaos ensues.

Presented by Barstool Sports, Drop A Pin takes you on a weekly adventure with Barstool's foreign correspondent, The Wonton Don, and Barstool personality, Uncle Chaps. Each episode, the fellas will Drop A Pin on a different spot across the globe, exploring the world from the iconic to the obscure. Sometimes they dive into serious topics, and other times, it's just about having a laugh as they uncover the weird, wild, and unexpected. Whether you’re looking for travel tips, hilarious stories, or a fresh take on global destinations, Drop A Pin delivers the perfect blend of humor and insight as they drop pins and share the unique experiences behind each one.

Uncle Chaps

The Wonton Don

Ari Shaffir's Nomad Phase Is Upon Us! | Drop A Pin Ep. 23

This week’s episode of Drop A Pin is loaded with wild travel stories and big laughs! @DonnieDoesWorld & @UncleChaps bring you the legendary Sam—the dedicated Barstool fan who joined Donnie on his now-infamous #Baldstool adventure. Buckle up for on-set plane seat antics, epic tales from India, and a touch of global intrigue. 🪑✈️

Timestamps:
00:53 Interview with Sam
2:04:04 Gettin' Cultured with Big T

🎤 Sam’s Wild Ride: From Baldstool to India

🔹 Baldstool Beginnings: Hear how Sam ended up shaving it all and following Donnie on an around-the-world escapade—truly a life-changing leap.
🔹 Highs in India: From navigating bustling streets to witnessing iconic landmarks, Sam and Donnie share their most memorable moments on the subcontinent. 🌏
🔹 Hezbollah Encounters in Lebanon: Get the inside scoop on Sam’s unexpected run-ins with Hezbollah—an adventure straight out of a spy thriller. 🤯
🎙️ THEN… Big T Takes the Mic on Being a LARGE Traveler 🏋️‍♂️💺
@BarstoolBigT joins to chat about the ups and downs of globe-trotting when you’re bigger than most airplane seats. 
🔹 Cramped Airline Struggles: Which carriers get a thumbs-up, and which leave you with bruised elbows? ✈️
🔹 Fit to Travel: How Big T handles seatbelt extenders, tight hotel rooms, and travel hacks every large traveler needs in their back pocket. 🤯
🔹 Surprisingly Comfy Destinations: Discover the places that truly welcomed a 6’5”+, 300-pound traveler—and the ones that definitely did not. 🏨
🔹 Sharing the Journey: Donnie, Chaps, and Big T compare stories of destinations that blew their minds, proving you never know what you’ll love until you explore. 🌐🔥
🔥 This episode offers comedy, culture, and a real look into how travel can surprise you around every corner (sometimes involving unexpected groups like Hezbollah).

💬 Tell us—what’s the most unexpected place you’ve found yourself while traveling? Drop your stories in the comments!

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🎧 Listen Now:

📍 Apple Podcasts | Spotify | YouTube
📲 Follow & Subscribe: @BarstoolSports | @DropAPinPod


#DropAPin #Baldstool #IndiaTrip #Hezbollah #Lebanon #BarstoolSports #SamTakesOnTheWorld #BigT #TravelPodcast #ComedyTravel #DonnieDoes #UncleChaps #Adventure #MustListen #GlobalAdventures

Follow The Wonton Don!
IG: thewontondon
TikTok: thewontondon
twitter: @donniedoesworld
FB: https://www.facebook.com/DonnieDoes/ 
Barstool: https://www.barstoolsports.com/bio/62720/donnie-does

Follow Uncle Chaps!
IG: @unclechaps
TikTok: @unclechaps
Twitter: @UncleChaps
Barstool: https://www.barstoolsports.com/bio/unclechaps

Hezbollah Detained Barstool Fan TWICE | Drop A Pin Ep. 25

In this episode of Drop A Pin, Donnie Does and Uncle Chaps are joined by comedian, world traveler, and globetrotting storyteller Giulio Gallarotti (@notjulio) to talk about the wild trip: vacationing in Iraq and Afghanistan. Yes, you read that right.

Chaps reflects on his time in Iraq through the lens of combat as a Marine, while Donnie and Giulio hilariously recount their civilian travels to the very same regions—not as soldiers, but as tourists. From ancient ruins to modern-day chaos, they compare what it's like to visit these countries with wildly different perspectives. 🌍✈️💥

Topics include:

Giulio’s bold decision to vacation in Afghanistan 🇦🇫

Touring Baghdad vs. surviving Fallujah 🇮🇶

How travel changes your worldview—even in warzones

Cultural gems, local hospitality, and surreal moments in conflict regions

Comedy, courage, and how far curiosity will take you

If you’ve ever wondered what it’s like to visit places most people only see in headlines, this episode will open your eyes—and probably make you laugh. It’s a wild, thoughtful, and unexpectedly inspiring ride.

🔔 Don’t forget to like, comment, and subscribe for more insane travel stories and global weirdness every week!

#DropAPin #GiulioGallarotti #TravelPodcast #IraqTravel #AfghanistanTrip #DonnieDoes #UncleChaps #CombatVsVacation #WarzoneTourism #MilitaryVsCivilian #TravelComedy #WorldExplorer #CrazyTravelStories #ChapsInIraq #GiulioInAfghanistan #GlobalAdventures

📍 Watch now on YouTube + Listen wherever you get your podcasts!

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Go to https://www.heydude.com today and find your perfect pair
 
Gambling problem? Call 1-800-GAMBLER (MI/NJ/PA/WV).
Help is available for problem gambling, call (888) 789-7777 or visit ccpg.org (CT). 
21+. Physically present in CT/MI/NJ/PA/WV only. Void in ONT. Eligibility restrictions apply. 
1 per new customer. Opt-in req. Min. net loss of $5 on eligible games to earn 100% of net losses back (“Lossback”) for 24 hours following opt-in. Max. $1,000 issued in Casino Credits for select games that are non-withdrawable, single-use, have no cash value, and expire in 7 days (168 hours). Terms: casino.draftkings.com/promos. Ends 4/27/25 at 11:59 PM ET. Sponsored by DK.

Iraq War Vet and Iraqi Tourist Squash Their Beef | Drop A Pin Ep. 24

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Drop A Pin is sponsored by BetterHelp. Visit https://BetterHelp.com/WONTON today to get 10% off your first month.

In this electrifying episode of Drop A Pin, Donnie Does and Uncle Chaps sit down with LOCASH, the country music duo behind hit songs like I Love This Life and One Big Country Song! From sold-out shows to terrifying moments in the sky, this episode is packed with wild tour stories, industry secrets, and some close calls.

What’s Inside This Episode?
🎤 The LOCASH Journey – How they went from songwriters to country music stars, writing hits for legends like Keith Urban & Tim McGraw.
🚛 Life on the Road – The highs and lows of touring across America, performing for thousands, and chasing the next big hit.
🏆 Chart-Topping Success – The grind behind making music that climbs the country charts and lands on playlists everywhere.
✈️ Near-Disasters in the Sky – The guys share wild plane stories that will have you double-checking your seatbelt the next time you fly!
🤣 Hannah Montoya Gets Cultured – Stuck in the dreaded middle seat, Hannah joins for another round of travel talk and culture questions with Donnie & Chaps.
🔥 This episode is a must-listen for country music fans, road warriors, and anyone who loves a crazy tour story!

📲 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts!

#DropAPin #LOCASH #CountryMusic 🎸 #TourLife 🚛 #OneBigCountrySong 🎶 #MusicIndustry #TravelStories ✈️ #PlaneDisasters #GettingCultured #BarstoolSports 🎤 #HannahMontoya #DonnieDoes #UncleChaps

Drop A Pin: On Tour with LoCash

Oh, God. Now you got junk just hanging out. Yeah. Now, that's a criminal offense, like. Right? Yeah, totally. Come on. Yeah. That point, you have to alert the flight attendant. So he rings a bell, right? You didn't ring a bell. I was texting the band. What are we going to do? Yeah. All right. Welcom

Wall Street’s Wild Days with Large
💰 This week on Drop A Pin, we’re heading to the heart of American finance—Wall Street. And who better to guide us through the highs, lows, and absolute insanity of the late ‘90s and early 2000s than Barstool’s very own @LargeBarstool?

🔹 History, Lore, and Scandals
Large shares firsthand stories from his time as a trader, painting a picture of a financial world fueled by high stakes, even higher egos, and legendary blow-ups. From the dot-com bubble to Enron’s implosion, the guys break down some of Wall Street’s most infamous moments.

🔹 The Wild Side of Wall Street
It wasn’t all about stocks and IPOs—Wall Street had its own culture of excess. Large pulls back the curtain on six-figure steak dinners, legendary cigar lounges, and martini-soaked afternoons that defined the era. Ever wonder where Gordon Gekko types actually hung out? This episode has you covered.

🔹 The Food Scene of Finance Bros
From old-school chophouses to legendary delis where deals were inked on the back of napkins, we explore the culinary institutions that fueled the bulls and bears of New York City. Plus, Large reveals his go-to power lunch spots that are still standing today.

🏛️💸 From the greed-fueled ‘90s to the Great Recession’s fallout, this episode is a deep dive into Wall Street’s most notorious era—through the eyes of someone who lived it.

🎙️ Getting Cultured
To close things out, @DonnieDoesWorld and @UncleChaps bring back Getting Cultured, answering travel questions and diving into some of the more questionable financial customs around the world.

Drop A Pin is sponsored by BetterHelp. Visit https://BetterHelp.com/WONTON today to get 10% off your first month.

👉 Listen now wherever you get your podcasts!
#DropAPin #WallStreet #FinanceBros #BarstoolSports #History #WallStreetScandals #TradingFloor #NYCFood #WallStreetLore #LargeBarstool

Wall Street's Wild Days with Large | Drop A Pin Ep. 21

So we're sitting there and, you know, 250 comes in for sale, and all of a sudden there's one guy in the crowd, I'll even say his name. His name is Danny Donner. And I see him open up his pants, take down his underwear. It's a point where I saw part of his stem. Reach in, grab it. Tucks boom. Leaves 

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Ari Shaffir's Nomad Phase Is Upon Us! | Drop A Pin Ep. 23

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