Cup to Cup

Cup to Cup | The Comedy Podcast

Comedy EN ↓ 603 episodes

Enjoy this naughty blend of hilarious Florida man adventures, dad jokes and a dash of 'Irresistible' charm in this sexy adult comedy podcast

Author

Cup to Cup

Category

Comedy

Podcast website

www.CuptoCuplife.com

Latest episode

Jul 2, 2026

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Episodes

"We're Dick Guys" - Ep. 74 28.04.2020

The whiskey is flowing in episode 74 and it's going right into Kevin's belly. The boys talk about what they miss the most since being isolated, Jason's answer pisses Chase off, but what doesn't piss Chase off. Is Star Wars and action movie? The debate didn't end the last episode, as Kevin gets his family feuding with each other on Facebook on the topic. DUUUVAL native and Kev's good buddy, Bill jo...

Story Time | The Craziest Sporting Event That Ever Happened 24.04.2020

From the start of the 1904 marathon to the end, it was a crazy spectacle of cheating, death defying actions, naps and even performance enhancing drugs? The outcome was so scandalous that the event was nearly cancelled for LIFE! Who - 1904 Olympic athletes What - 1904 Olympic Marathon Event Where - St. Louis When - 1904 Why - Because shit got crazy Mansaped.com - Use code "cuptocup" to save yoursel...

Mute Your Mic Brenda! - Ep. 73 21.04.2020

Florida man never lets us down as Chase goes absolutely off his ringer with his answer. Who knew so much preparation goes into him watching porn. We try our damndest to try and narrow down ideas for our next bracket, yet somehow end up arguing about 80's vs 90's. Only to be topped by Jason and Kevin listening to Chase nerd out over board games. We are joined by Chase's cousin and friend of the sho...

What's on Tap | TLH Beer Society 16.04.2020

If you are bored with your current beer selection and need to discover some good Florida Beer give this episode with TLH Beer Society a listen. Matt and Danny from TLH Beer Society explains how they ended up being just a twitter account about local Tallahassee beer to having their own ESPN Radio show all about craft beer. Don't worry, its not just a history lesson, we have a blast with our Lonely...

Jason is a scared little b**** - Ep. 72 14.04.2020

Jason swears he's not a bitch for being scared of this one thing...but is he alone? We find out who the wives think Jason and Kevin would pick as their vice presidential candidate and the answers are surprising. While talking about our next yet to be decided bracket Kevin gets confused about dangerous animals and has an interesting take on things. We have our friend Ryan Phenix on for 7 minutes in...

Shawn Bassett | Cars, Bikes & Deadly Races - Ep. 71 07.04.2020

The title of the episode says it all. Do we need to say more? Our friend, Shawn Bassett, owner, racer (bike & car) and the mechanic/designer of the famous and unique 1972 240z, that will probably be the most original car to race at the world famous race track, Pikes Peak, joins the podcast. (damn, that was a lot to say) As most know, we are all idiots, so Shawn was kind enough to break everything...

Story Time | The Drunk Receiver 02.04.2020

Discover the iconic story about a Green Bay Packer player that helps win his team a Super bowl, while hungover... Who - Max Mcgee What - Super Bowl I Where - Los Angeles Memorial Coliseum in Los Angeles, California When - January 15, 1967 Why - Because sometimes women and beer over everything Thanks for listening and supporting us! Please subscribe, drop us a review and share us to a friend. Serio...

Comedian Jud Danger | My Girl Left Me Because of Andy Dick - Ep. 70 31.03.2020

Would you believe me if I told you Andy Dick might have caused a breakup? Would you believe me if I told you it had to do with a dog, poop and alcohol? Our friend and up and coming comedian Jud Danger joins the crew for some epic story telling. I'll reveal 3 stories that are fresh on the brain. First, Andy Dick plays a role in a breakup, he also crashes a carwash, a not so "great" nazi joke was pu...

Story Time | Why We Call Them Hookers 26.03.2020

Discover why we call prostitutes hookers and why one General is remembered not for his military skills but for his "parties". Who - General Joseph "fighting Joe" Hooker What - Hooker Where - America When - Civil War Era Why - Hookers are real people too Thanks for listening and supporting us! Please subscribe, drop us a review and share us to a friend. Seriously, tell a stranger! As always, check...

Introducing Story Time 25.03.2020

For your entertainment pleasure,, we bring you an all new series from Cup to Cup, welcome to Story Time. A series all about stories that probably aren't in your history books but could make for a great story at the bar. No subject is off limits. We'll discuss one item each episode about people, an event or moments in history that you may or may not know about. Actual research and real stories all...

The Phrase Game - Ep. 69 24.03.2020

We drop a new game thats played during the entire episode and YOU COULD WIN FREE MERCH if you play along. We go over the rules in the beginning of the episode, so don't miss it! Cinnamon Toast Crunch or Honey Nut Cheerios, which one will take the trophy? After 20 weeks, we crown the Cereal Bracket Champion…will it be an upset? Who else wanted an attempt at THE CRAG from the Nickelodeon show, Guts?...

What's on Tap | Oyster City Brewing 19.03.2020

Have you ever visited Apalachicola, Florida or had a the iconic "Hooter Brown"? Well if you answered yes or no, listen to this awesome episode with Clayton Mathis from Oyster City Brewing. We have another jack of all trades joining the podcast, Clayton Mathis aka Head Brewer. He has done everything from cleaning tanks, to brewing to managing the brewery and we learned a ton! Make sure to stick aro...

Steaks Dropping from Pants & Toilet Paper Rants - Ep. 68 17.03.2020

Are you looking for some deep & rich St. Patricks Day history? Would you like it to come from the 3 least qualified individuals on a podcast? You're welcome, because Kev gives a brief lesson right off the bat. An episode full of St. Patrick shenanigans, including a special Name that Show, The Best Cereal comments, a lot of crickets are heard, things falling out of a Florida Mans pants and a very h...

Comedian Daisy Tackett | We Only Offended Her 4 Times - Ep. 67 10.03.2020

What would you do if you were catfished by a handless man online? Comedian Daisy Tackett graciously explains this insane but hilarious experience. After watching Daisy tear down a wild and hostile crowd, Jason thought it be a great idea to bring her on and holy shit it was. Not only does she dive into how group therapy got her into Comedy but she also talks about Jacksonville booing her, puts Kevi...

Should Strippers Wear Helmets? - Ep. 66 03.03.2020

Have you ever wonder what the news would be like if we were the anchors? We bring you, "Cup to Cup, this week in news" Highlighting the many things the crew discusses behind the scenes- minus the politics of course. The episode is also PACKED with some great segments too. Jason brings in a disturbing What if, Correct Me if I'm Wrong stumps us (again) and we have another awesome Name that Song and...

"This is a Weird Florida Man" - Ep. 65 25.02.2020

Can you guess the Florida Man Headline that gets both the guys grossed out and speechless? Hint, it includes a body part. Siri is also back to teach us the many ways you can describe a... You know we aren't going to tell you here, so check it out after 7 minutes in Heaven and sorry if we offend you. The crew does push through a tough final Elite 8 Matchup though, we have some great Fill in the Bla...

Eating Worms for Protein - Ep. 64 18.02.2020

Have you ever eaten insects or bugs before? Do you want to? We try a company called Crunchy Critters who provided us worms mixed in with other ingredients, live on the podcast. It wasn't as bad as you think but it was an awesome experience. The crew also dives into some deep conversations about pain tolerance, if we could handle a pregnancy and some terrible insults girls have told them. We also h...

Hunter McIntyre | Unicorns & Obstacle Racing - Ep. 63 11.02.2020

Want to hear from Hunter McIntyre, the best Obstacle Course Racer in the world & laugh your ass off? You know you do. Hunter, aka The scotch Irish beauty, is a Six-time Obstacle Course Racing World Champion, Four-time Obstacle Course Racing National Champion, Three-year Steve Austin's Broken Skull Ranch Champion and Two-time Tough Mudder X Champion. Hunter talks about these achievements, how he go...

What's on Tap | Ancient City Brewing 06.02.2020

From pairing beer to putting out a basil wheat that we all have to try, Ancient City Brewing in St. Augustine, Florida needs to be on your list. Shane from Ancient City Brewing talks about both locations, one in the heart of St. Augustine and another just outside of the city. Shane also goes over how it started, some sweet events that are coming up and the beer they brew. Shane also delivers some...

Is Sleeping Naked Weird? - Ep. 62 04.02.2020

An episode that should have 5 titles. The podcast starts off with a weak Florida Woman arrest, a David vs Goliath cereal matchup and a heated Name that Show. And I do mean heated... It gets even better when we are graced with none other than Mayor Adamson and it gets weird again with a sleeping naked lesson by our boy Jose on This is Where We Fuck Up. So fasten up... *The Cup to Cup Rundown* Flori...

What Would You Ask Your Dog? - Ep. 61 28.01.2020

If you had one question to ask your pet and could get answer back, what would it be? We find out the guys all have different intentions with their questions. Chase also gets super close to getting another Florida Man right, Kev drops another angry I Don't Get, one of us is not smarter than a kid and we wrap up the final Sweet 16 show down for the The Best Cereal Bracket to move us to the Elite 8....

What's on Tap | 3 Daughters Brewing & TLH Beer Fest 22.01.2020

Our Craft Beer shenanigans are back with 2 interviews! First one with our buddy Bob from 3 Daughters Brewing and the second with our boy Ben from the TLH Beer Festival. Discover how 3 Daughters got their name, how insane their distribution is and what beers you need for the beach. And make sure to stay tuned after that interview to find out out some of the 72 breweries, including 3 Daughters Brewi...

Are Balls Attractive to Anyone? - Ep. 60 21.01.2020

Are you ready for one estranged Florida Man story? It's not right and the guys had a hard time understanding why. Not to mention, we've finally got a point on the board from "Name that Show". We also dropped a new segment called "I don't get it" and it might be the most controversial thing said on the podcast. Please keep the hate mail to a PG-13 level. Cheers *The Cup to Cup Rundown* Florida Man...

What 8 Hours of Sleep Feels Like - Ep. 59 14.01.2020

Welcome back! A brand new year comes with a brand new season that includes a revamped sports segment and 3 new segments, 2 of which are on this episode. Speaking of this episode...You'll discover a strange reason to break into a building during our Florida Man segment and some intense hatred towards the cowboys and what we think of Booger McFarland. Joined by our boy Joe Pepe Lets not forget Kevin...

Season 2 Trailer 12.01.2020

Cup to Cup is back for a second season, with our first episode of the season dropping on January 14. (Preview of episode 59 at the end) If you didn't catch last season, don't worry about it. Since we're bringing back our classics like Florida Man, Would you Rather, Dad Tips and our craft beer series, Whats on Tap, you'll catch right up. But we are giving you 3 new segments, Smarter than this Kid p...

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