Drop A Pin

Barstool Sports
  • 4.9 (485)
  • PLACES & TRAVEL
  • UPDATED WEEKLY

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.

  1. 3D AGO

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

    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! Try your first month of BlueChew FREE when you use promo code DROP -- just pay $5 shipping. https://BlueChew.com 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.

    2h 10m

  2. MAR 17

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

    🌎 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.

    2h 3m

  3. MAR 10

    Drop A Pin: On Tour with LoCash

    Try your first month of BlueChew FREE when you use promo code DROP -- just pay $5 shipping. https://BlueChew.com Go to https://www.heydude.com today and find your perfect pair, the official comfort shoe of Barstool sports 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

    1h 22m

  4. MAR 3

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

    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

    2h 12m

  5. FEB 24

    A Look Inside The Weird Wide World of Sam Tallent | Drop A Pin Ep. 20

    🎙️ Drop A Pin: Sam Tallent Takes Flight + Traveling as a BIG, BIG Man ✈️🌍 🚨 This week’s episode is a must-listen for comedy and travel lovers! @DonnieDoesWorld & @UncleChaps welcome the hilarious Sam Tallent (SamTallent) into the studio, where he becomes the first-ever guest to sit in our studio plane seats! 🪑✈️ 🎤 Sam Tallent: The Comedian Who’s Been Everywhere 🔹 The Art of Small-Town Comedy: Sam shares wild stories from performing in tiny venues across America, where the crowds are rowdy, unpredictable, and sometimes too involved. 🎭🏚️ 🔹 Lessons from the Road: From grinding through dive bars to playing real comedy clubs, Sam dives into what it takes to make it in stand-up. 🔹 Performing Around the World: Comedy isn’t just an American game—Sam has brought his act to Europe, Asia, and beyond. 🌍✨ 🔹 His Love for Japan & Scandinavia: Why he keeps going back, what makes those places special, and what he’s learned from their cultures. 🍣🇯🇵🏔️🇳🇴 🔹 His Own Travel Show?! Sam teases a potential new project where he brings his comedic lens to international exploration. 👀📺 🎙️ THEN… Barstool Beef on Being a BIG, BIG Traveler 🏋️‍♂️💼 @BarstoolBeef joins the crew to talk about the unique challenges of traveling as an absolute unit. 💪😅 🔹 The Airline Struggle: Which airlines are the best (and worst) for larger passengers? Where can a big man get some elbow room?! 💺✈️ 🔹 Packing Tips for XXL Life: Finding clothes that fit, packing efficiently, and dealing with tiny hotel closets. 🎒👕 🔹 Seatbelt Extenders, Tiny Hotel Beds & Cramped Spaces: The unspoken realities of big-guy travel—how to avoid awkward moments & what hacks make it easier. 🛏️🤯 🔹 Best Destinations for Big Guys: Which places are actually comfortable for larger travelers? Spoiler: Some spots are NOT built for a 6’5”, 300+ pounder. 🌎😅 🔥 This episode has it all—comedy, travel tips, chaos, and a deep appreciation for Sam Tallent’s journey. 💬 Let us know—what’s the worst travel experience you’ve ever had?! Drop it in the comments! Try your first month of BlueChew FREE. Visit https://BlueChew.com for more details and important safety information, and we thank BlueChew for sponsoring the podcast. Find your perfect pair at https://www.heydude.com today! 🎧 Listen Now: 📍 Apple Podcasts | Spotify | YouTube 📲 Follow & Subscribe: @BarstoolSports | @DropAPinPod #DropAPin #ComedyTravel #SamTallent #BarstoolBeef #BigGuyTravel #Japan #Scandinavia #TravelTips #BarstoolSports

    1h 44m

  6. FEB 17

    Billy Football Breaks His Silence on Future at Barstool (And Africa) | Drop A Pin Ep. 19

    Billy Football Breaks His Silence on Future at Barstool (And Africa) | Drop A Pin Ep. 19 Episode Breakdown: ✅ Billy Football Returns! 🏟️🎤     •    Why he left Barstool & what he's been up to     •    Coaching football in Africa 🏈🌍     •    His wild adventures in Botswana 🇧🇼🐘 ✅ Getting Cultured w/ Jon Gruden 🏆🔥     •    Coaching football in Europe 🏈🇪🇺     •    Where he wants to vacation next (hint: NOT Oakland 😆)     •    His thoughts on the global growth of football 📲 Follow Us: 🔹 Drop A Pin: [@DropAPinPod] 🔹 Donnie: [@DonnieDoes] 🔹 Chaps: [@UncleChaps] 🔹 Billy Football: [@Billyhottakes] 🔹 Jon Gruden: @barstoolgruden #DropAPin 🌍 #BillyFootball #JonGruden #Football #Travel #Botswana #NFL #BarstoolSports #Podcast

    2h 25m
  7. Down Yonder In Mississippi w/ Brandon Walker

    FEB 10

    Down Yonder In Mississippi w/ Brandon Walker

    🎙️ Drop A Pin: Mississippi Madness w/ Brandon Walker 🎙️ 🚨 This week, Drop A Pin heads down south to the great state of Mississippi 🌊🌾—a place many say is the worst state in the U.S. (stats don’t lie 📊), but Brandon Walker (@BWalkerSEC) ain’t hearing ANY of that nonsense. Can a state that gave us Ben Mintz (@Mintzy) really be that bad? 🤔 🐟🎣 The crew dives deep into all things Mississippi, including: ✅ Fishing (the lifeblood of the state) 🎣 ✅ Catfish (the real king of southern cuisine) 🐟🍽️ ✅ Coleslaw (Is it elite or trash? Let’s debate) 🥬🤨 ✅ West Point High School (the pride of the state) 🏈💪 ✅ Worms (yes, worms… just listen) 🪱😂 Brandon defends his home state with PASSION 🔥, and even Donnie (@DonnieDoesWorld) & Chaps (@UncleChaps) can’t help but respect it. 🎧 Listen now for laughs, southern charm, and a whole lot of Mississippi pride 🇺🇸 #HailState #SouthernHospitality #CatfishKings #DropAPin 📲 Follow for more: 🐉 @DonnieDoesWorld 🎙️ @UncleChaps 🌍 @DropAPinPod

    1h 37m
  8. Jerry Escobar And The Coked-Up Hippos: DAP Colombia

    FEB 3

    Jerry Escobar And The Coked-Up Hippos: DAP Colombia

    🎙️ Drop A Pin: Exploring Colombia with Jersey Jerry 🇨🇴 On this episode of Drop A Pin, Donnie Does and Uncle Chaps sit down with Jersey Jerry (@Jerrythekid21) to talk about his time in Colombia. From the country’s complicated past to its evolving present, Jerry shares his thoughts on: 🏙️ His favorite spots – where to visit and what to skip 🏚️ Pablo Escobar’s legacy – the real impact vs. pop culture myths 🦛 The Hippo Problem – Escobar’s pets turned invasive species 🍽️ Food scene – what’s worth trying and what surprised him 💰 Cost of living – how far your dollar can go 🏡 Buying property in Colombia? – Donnie, Chaps, and Jerry debate making it happen After the interview, Chaps and Donnie take a deeper dive into: 🕰️ Colombia’s history – beyond the Narcos stereotype 🌎 Cultural differences – what travelers should know ✈️ Travel tips – safety, must-visit places, and getting the best experience 📍 Plus, in the Gettin’ Cultured segment, Donnie and Chaps answer questions from the Pin Heads about Colombia, travel etiquette, and what they’d do first if they moved there. Got a question for a future episode? DM us or drop a comment! 🎧 Listen now on Apple Podcasts & Spotify 🔗 Drop A Pin on Apple | Drop A Pin on Spotify Follow us for more travel takes & behind-the-scenes content: 📲 @DonnieDoesWorld | @UncleChaps

    1h 52m
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    Hosts & Guests

    4.9
    out of 5
    485 Ratings

    About

    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.

    Information

    • Channel
      Barstool Sports
    • Creator
      Barstool Sports
    • Years Active
      2024 - 2025
    • Episodes
      24
    • Rating
      Explicit
    • Copyright
      © 2025 Barstool Sports, Inc.
    • Show Website
      Drop A Pin

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