Cup to Cup | The Comedy Podcast
Enjoy this naughty blend of hilarious Florida man adventures, dad jokes and a dash of ‘Irresistible’ charm in this sexy adult comedy podcast
Episodes
September 11, 2025 • 96 mins
From carrots ruining an entire day to refusing to wait five minutes at Chili’s, the guys are back with another round of hilarious chaos. This week we cover: Jason’s restaurant meltdowns and backup plan strategy Kevin’s irrational carrot rage and cheese-stick vs shredded-cheese parenting battle A wild Florida Man headline straight out of The Villages 👀 Chris ripping The Crow remake to shreds while Jason defends Disney’s ...
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September 9, 2025 • 68 mins
NFL: -Overreaction with your team after Week 1 -Pick Em Update - Don’t talk about your team -FSU: -FSU v East Texas A&M (Noles in Top 10) -FSU Hoops recruiting is on fire Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces)
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August 28, 2025 • 82 mins
From vibrating fitness boards and poop-in-the-pants confessions to Florida tornado nightmares and a Florida Man lawnmower DUI, this week’s episode is absolute chaos. The guys debate which everyday disasters ruin your day the fastest (spoiler: wet socks are pure evil), relive the scariest weather they’ve survived, and roast Kevin’s “caffeine journey” before diving into a wild Florida Man headline out of Polk County. Add in random Tw...
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August 26, 2025 • 50 mins
Which two NFL 2024 Division champs will repeat? NFL: -Jags/Dolphins W&Ls -FSU/College Football -5 Days until kickoff! --Tenn/Ole Miss 2021 Game Stats -MLB: -Fantasy Studs & Duds/Fantasy Update Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces)
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August 20, 2025 • 99 mins
This week the guys are all over the place — from a Florida Man who broke into a house just to cook dinner and take a bubble bath, to debating which U.S. cities are actually overrated. Chase rants about Disney prices, Chris suffers through bad horror movies, and Jason ends up with sand in places sand should never be. Also inside: Sweet tea and grits get dragged (southerners, brace yourselves) A review of way-too-many bad movies...
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August 13, 2025 • 94 mins
The gang debates a galaxy-shaking matchup — The Incredible Hulk vs. Darth Vader — and things get weird fast. Along the way, we argue about the glory (or disgrace) of grits, uncover the Florida couple selling “tickets to ????,” moan our way through a “What Feels Better?” segment, and roast each other’s questionable fashion choices. Oh, and there’s plenty of Florida Man chaos, red-light rants, and friendship trust trees getting burne...
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August 6, 2025 • 106 mins
From glizzies to GoldenEye, this episode is pure chaos. Kevin, Jose, Chase, and Chris go all in on the most important debate of our time—what video game deserves a remaster—and somehow detour into Chuck E. Cheese credit card fraud, Florida Man headlines, and the mystery of why “Sorry” is a terrible answer. You’ll also get the “She’s Always Right” relationship test, fast food rankings that will make you question your friendships, an...
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August 6, 2025 • 64 mins
We start with Chris’ questionable drink choices, detour into Kevin’s Dunkin’ disaster, and then dive headfirst into the ultimate sports “what if” — picking a championship team that isn’t our own. NFL, college football, fantasy baseball trash talk, MLB bench-clearing nostalgia, and even a little wrestling chaos. It’s sports, sarcasm, and stupidity in equal measure — just the way we like it.
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July 31, 2025 • 111 mins
Episode 307 is stacked with chaos. We welcome in new guest host Andy and immediately derail with Florida Man impersonations, emotional dad tips, wild 20s advice, and VHS home video nostalgia (complete with broom choreography). Then comes the bracket — action movie heroes go head-to-head and the debate nearly ends the show. Spoiler: Jason loses his mind over T2. Also inside: ⚡️$375 rent war stories ⚡️Why documenting grandma is cruci...
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July 29, 2025 • 81 mins
WTF is the Canadian Football League doing? MLB: -Fantasy Studs & Duds NFL: -Preseason Starts Thursday -Jefferson already injured -Rough start for some QBs -ESPN might be acquiring NFL Network & Redzone? FSU: -FSU Hoops Non-Conference -Buying into Norvell/TC passion from ACC Kickoff? Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB
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July 24, 2025 • 94 mins
This week, the boys are back from vacation and full of hot takes, deep regrets, and even deeper shoe shame. Kevin opens up about the $200 aquarium mistake (and we mean mistake), Jose coughs his way into a 5-minute timeout, and Chase gets roasted from head to toe — mostly because both are covered in gear from 2005. We also dive into: Vacation beard compliments gone too far The Florida Man who stuffed what down his pants?! Ou...
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July 22, 2025 • 69 mins
-Would you rather be a fan of a team that nobody talks about or a team that everyone hates? NFL: -ChatGPT predicted the 2025 NFL Playoffs -Which NFL team is currently America’s team? - Where do you have the Steelers now? Additions of Ramsey and Jonu Smith (with Rodgers and DK Metcalf) MLB: -Fantasy Studs & Duds -Make one bold prediction about your team for the rest of the season -Acuna’s Amazing Throw FSU: -Recruiting Cl...
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July 10, 2025 • 92 mins
We start this one off hot—Kevin’s having a meltdown, Jason’s picking fights, and SOMEONE is locked out of their own damn computer. Meanwhile, Chris is pretending to be organized while secretly rigging the the BIG BOARD. We dive into the shady world of dealership oil changes, how to blow $10 million (with zero tax planning), and what exactly a meth-fueled Oregon man was doing when the cops showed up (spoiler: it’s NSFW). There’s als...
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July 3, 2025 • 106 mins
This week’s episode starts like a normal podcast... and then quickly nosedives into peak chaos. The guys dive into hot takes, donation drama, and whether Kevin is a “supreme leader” or just loud. One minute we're talking Pride Month merch, the next we’re debating Twitch follow etiquette, and somewhere in between, someone gets roasted for drinking alone. Again. There’s arguing, there’s laughter, and there’s at least one moment where...
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July 1, 2025 • 77 mins
Its sports... MLB: -Fantasy Studs & Duds -Better chance to win the HR Derby: Acuna or Raleigh? NFL: -Which 2024 Playoff Team will miss the playoffs? 🏈 American Football Conference (AFC) Kansas City Chiefs – AFC West Champions (15‑2) Buffalo Bills – AFC East Champions (13‑4) Baltimore Ravens – AFC North Champions (12‑5) Houston Texans – AFC South Champions (10‑7) Los Angeles Chargers – Wild Card (11‑6) Pittsburgh ...
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June 26, 2025 • 90 mins
t’s been a minute but the full squad is back together (including Jason from Texas!) We open up the episode talking about a good song if you are caught in a bar fight. Florida Man takes us to Gulf Breeze involving a dude and some cooking oil. Chris has the latest Random Twitter Finds involving C items. Kevin has his weekly Dad Tip and Jose holds us accountable with WWFU. Chase wraps up the episode with Trivia for the Big Board. S...
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June 18, 2025 • 81 mins
We still have members of the crew missing as it’s a trio squad for this episode. They open up the episode talking about more traumatizing than they realize. Florida Man takes us to Kentucky involving “Cowboy Cody”. Kevin has the latest Picture Time for us with some help from his new best friend. Kevin also has his weekly Dad Tip and Jose is back for WWFU. Chris isn’t here but does have a Would You Rather and Chase has Spot the Fa...
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June 17, 2025 • 60 mins
NFL: -Give me a reason why your NFL team will win the Super Bowl this year and give me one reason why they won’t win it this year. MLB: -Fantasy Studs & Duds -Who would you rather have for a full career: Derek Jeter or Chipper Jones? FSU: -College Gameday not coming to FSU for Corso’s final show; Which game should he be back to be honored for? -Is this the angriest the FSU fan base has ever been?
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June 11, 2025 • 69 mins
Some of the crew is still dragging after the Big 300 so it’s only a trio squad tonight. We open up the episode talking about which cars are driven by a**holes. Florida Man actually takes us back to Delray Beach. Chris has the latest Movie Time showing Chase’s obsession with Natalie Portman. Kevin has his weekly Dad Tip and Chris has the latest Random Twitter Finds mixing hot and cold. Mayor Andy steps in this week for WWFU from the...
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