Drop A Pin

By Barstool Sports

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

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How many episodes does Drop A Pin have?

The podcast currently has 30 episodes available.

Drop A Pin episodes:

May 05, 2025 Big Cat Signs Off on Barstool Australia | Drop A Pin Ep. 30
🚨 Brand‑new destination alert! @DonnieDoesWorld & @UncleChaps welcome @BarstoolBigCat into the studio for a globe‑trotting brainstorm, some serious college‑town nostalgia, and a rapid‑fire book recs for the Pinheads. 🪑✈️
Timestamps:
00:00:23 Big Cat Interview
00:30:33 Donnies Barstool Australia Pitch
00:52:14 Gettin Cultured
🎤 Big Cat Takes the Middle Seat
🔹 Limited Stamps, Endless Adventures – Big Cat admits he’s more domestic king than international jet‑setter (spoiler: his passport looks suspiciously crisp). 🤷‍♂️🌍
🔹 The Australia Pitch – Donnie floats a wild plan: hosting a competition for a one year content contract to hunt down Barstool’s first Australian hire. Will Big Cat bite? 🦘📹
🔹 Campus Crawl Hall of Fame – Big Cat ranks his favorite college towns, breaking down what makes a campus elite: walkability, dive‑bar density, mascot chaos, and late‑night food that slaps. 🏈🎓🍻
📚 Gettin’ Cultured: Pinhead Reading List
Donnie & Chaps swap their go‑to books—travel memoirs, military history deep cuts, and a couple of curveballs you’d never expect. Perfect additions for your carry‑on Kindle or couch stack. ✈️→📖
⸻
🎧 Listen / Watch Now
Apple Podcasts | Spotify | YouTube
📲 Follow & Subscribe
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: @UncleChapsBarstool: https://www.barstoolsports.com/bio/13906103/chaps
#DropAPin #BigCat #AustraliaPitch #CollegeTowns #BookRecommendations #TravelPodcast #BarstoolSports
⸻
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Follow The Wonton Don!
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twitter: @donniedoesworld
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Barstool: https://www.barstoolsports.com/bio/62720/donnie-does
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1h 13min
April 28, 2025 The Legend of Don The Beachcomber (Bora Bora Honeymoon Recap) | Drop A Pin Ep. 29
🎙️ Drop A Pin: French Polynesia Vlogcast 🌺✈️
🚨 This week’s episode is a one-plane-cockpit special—just @DonnieDoesWorld & @UncleChaps taking you on a tropical ride through French Polynesia! It’s our first-ever VLOGCAST (be sure to checkout the episode on youtube), packed with never-before-seen footage, fresh dad updates, and a tiki-bar legend that kicked it all off. 🪑🎥
Timestamps:
1:06-10:57 Intro/Housekeeping
10:58-32:25 French Polynesia Discussion
32:26-1:38:43 Honeymoon Talk
1:38:44-1:50:50 Gettin’ Cultured with PFT
🎤 The Solo Flight: Chaps & Donnie Catch Up
🔹 Fact-Check & Feedback – The guys tackle some spicy comments about past episodes’ “accuracy,” and set the record straight
🔹 Baby on Board – Donnie reveals the wild play-by-play from his first ultrasound (spoiler: it was wild). 🤰📈
🌺 Don the Beachcomber & the Honeymoon Game Plan
🔹 How a 1930s tiki pioneer inspired Donnie’s dream honeymoon locale. 🍹🏝️
🔹 Deep cuts on tiki culture, cocktail lore, and why French Polynesia still feels like vintage escapism.
🎥 Vlogcast Premiere: French Polynesia Honeymoon Highlights
🔹 Abandoned Resorts, peak hippo mode, over-water bungalows—raw travel footage straight from Donnie’s camera roll.
🔹 Unexpected mishaps (ever try driving a boat with zero instruction?) and the ultimate sunset flex. 🌅🚤
🎙️ THEN… PFT Commenter Drops In for Gettin’ Cultured 🎰🌎
@PFTCommenter joins the cockpit to ask: “Is there Las Vegas of every country?”
🔹 Rapid-fire lightning round—Paris? Macau? Punta del Este? Who wins the neon crown?
🔹 The fellas draft their top “sin cities” around the world and debate which ones actually pay off in vibes.
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1h 51min
April 21, 2025 Dave Portnoy Was Offered 4 Million To Bring Historic Pizza Fest to Saudi Arabia | Drop A Pin Ep. 28
This week on Drop A Pin, Donnie and Chaps are joined by Barstool founder and El Presidente himself, Dave Portnoy, for a deep dive into one of his favorite places on Earth: Nantucket.
🔑 In this episode:
🏠 Why Dave Loves Nantucket: Portnoy shares how he first discovered the island
💸Dave talks about the current state of Nantucket’s insane real estate market
⚓ The Island’s History: Donnie breaks down how Nantucket went from being the whaling capital of the world in the 1800s to a high-end getaway destination.
🍽️ Scalloping on His Property: Dave explains how he found himself with active scalloping rights on the lot he bought—and what that actually means in terms of local rules and seasonal seafood.
🍕 Pizza Reviews in Saudi Arabia: Dave may be doing a pizza fest in the Middle East
💅 Getting Cultured with Annika: In our recurring segment, Barstool's Annika asks talk about getting some work done abroad
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🎧 Drop A Pin is live now on YouTube, Spotify, and Apple Podcasts.
📍#DropAPin #BarstoolSports #Nantucket #OneBite #SaudiPizza #ElPresidente #BarstoolTravel #ScallopingSeason
Follow The Wonton Don!
IG: thewontondon
TikTok: thewontondon
twitter: @donniedoesworld
FB: / donniedoes
Barstool: https://www.barstoolsports.com/bio/62...
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1h 55min
April 14, 2025 Finding Yourself in Florence feat. Jenks | Drop A Pin Ep. 27
🎙️ Drop A Pin: Frank “The Tank” Fleming’s Producer, Matthew Piper Jenks Takes Flight + Embracing the Florentine Spirit ✈️🇮🇹
🚨 This week’s episode is a must-listen for travel enthusiasts and Italy aficionados! @DonnieDoesWorld & @UncleChaps welcome the one and only Matthew Piper Jenks—producer to Frank “The Tank” Fleming—who shares his incredible experiences living in Florence. From intense Calcio Storico matches to the captivating Palio di Siena, Jenks and Donnie swap stories of adrenaline-fueled spectacle and genuine cultural immersion. You’ll hear how one warm-hearted Florentine family welcomed Jenks like their own son, creating memories he’ll never forget.
Timestamps:
Interview With Jenks - 00:00:44
Florence Discussion - 1:33:16
Gettin' Cultured with Mark Titus - 2:12:42
🎤 Matthew Piper Jenks: The Man Behind the Legend of Frank The Tank & His Life in Florence
🔹 Calcio Storico: Jenks and Donnie break down the historic—and sometimes downright brutal—sporting event and why it’s a must-see for anyone visiting Florence. ⚽
🔹 Palio di Siena: Hear about the centuries-old horse race that captivates an entire city, and learn what makes this tradition a true bucket-list experience. 🏇
🔹 Florence Family Ties: Jenks reveals a heartfelt story of how a local Florentine family embraced him, giving a fresh perspective on Italian hospitality. ❤️
🎙️ THEN… Mark Titus Joins for “Gettin' Cultured” for advice on Fatherhood & Travel ✈️👨‍👧
Mark Titus slides into the airplane seat for a candid chat about his upcoming journey into fatherhood and his burning desire to keep traveling.
🔹 Parenting on the Road: How to prepare for family trips without losing your mind—or your passport. 🍼🌍
🔹 Advice from a Veteran Father: As a seasoned father Chaps share his top tips and travel hacks for traveling with a child.
🔥 This episode has it all—Italian sports, heartfelt stories, culture-shock anecdotes, and fresh perspectives on balancing fatherhood with a passion for travel.
💬 Let us know—what’s your favorite Italian tradition or destination? Share in the comments below!
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21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 5/18/25 at 11:59 PM ET. Sponsored by DK.
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Download the Gametime app today and use code DROP for $20 off your first purchase
GAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY).
Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD).
21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 5/18/25 at 11:59 PM ET. Sponsored by DK.
Control Body Odor ANYWHERE with @shop.mando and get $5 off off your Starter Pack (that’s over 40% off) with promo code WONTON at https://shopmando.com! #mandopod
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🎧 Listen Now:
📍 Apple Podcasts | Spotify | YouTube
📲 Follow & Subscribe: @BarstoolSports | @TheDropAPinPod
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/13906103/chaps
...more
2h 25min
April 07, 2025 Thai'd Up in Bangkok | Drop A Pin Ep. 26
🚨 This week’s episode is an absolute can’t-miss for all you travel junkies! @DonnieDoesWorld & @UncleChaps dive into their unforgettable adventures in Thailand—from Donnie’s early content creation days to the wild stories to crazy festival experiences
Donnie & Chaps: Life & Laughs in Thailand
• From the Streets of Bangkok to the Islands: Hear about the nightlife, hidden gems, and local delicacies that left Donnie & Chaps wanting more! 🌃🌴
• Donnie’s First-Ever Content Series: Get the backstory on how Donnie took the leap into vlogging, the challenges he faced, and how Thailand played a massive role in his journey. 🎬💥
• Tyler, a new Barstool producer, reveals how he got busted smoking weed in Thailand—and the hectic bribe he had to pay to dodge trouble with the cops. 🚨💰
• Lessons Learned: From facing local laws head-on to making it out unscathed, Tyler shares the adrenaline-packed story and how it changed his perspective on traveling. 😬🌏
Gettin’ Cultured with Steven Cheah
• Why Do Different Countries Drive on Different Sides of the Road?: Steven stops by to break down the fascinating history, cultural quirks, and sometimes dangerous realities behind left-side vs. right-side driving. 🚦🤔
• Travel Adjustments & Tips: Whether you’re a first-timer or seasoned globetrotter, learn how to adapt when hitting the roads in countries with traffic flowing in “the other lane.” 🛣️✅
🔥 This episode is loaded with Thai memories, production secrets, and global insights. It’s a must-watch for anyone craving a little wanderlust!
Let us know—what’s your top tip for staying out of trouble abroad? Drop it in the comments!
Listen Now:
📍 Apple Podcasts | Spotify | YouTube
Follow & Subscribe:
@BarstoolSports | @TheDropAPinShow
#DropAPin #ThailandTravel #PeakinSeries #DonnieDoes #UncleChaps #StevenCheah #BarstoolSports #DrivingAbroad #CultureShock
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
...more
2h 10min
March 31, 2025 Hezbollah Detained Barstool Fan TWICE | Drop A Pin Ep. 25
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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Go to https://www.heydude.com today and find your perfect pair
Gambling problem? Call 1-800-GAMBLER (MI/NJ/PA/WV).
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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.
🎧 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!
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Twitter: @UncleChaps
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...more
2h 15min
March 24, 2025 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!
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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.
...more
2h 11min
March 17, 2025 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.
...more
2h 4min
March 10, 2025 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
...more
1h 22min
March 03, 2025 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
...more
2h 13min

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The podcast currently has 30 episodes available.

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The Dime Package

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Friday Night Pints

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One Minute Man

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