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Cup to Cup | The Comedy Podcast

Comedy Podcasts

From Florida Man headlines to unique guests, one of a kind bracket tournaments or their quirky segments, you’ll find yourself yelling, laughing and possibly learning a thing or two.

From Florida Man headlines to unique guests, one of a kind bracket tournaments or their quirky segments, you’ll find yourself yelling, laughing and possibly learning a thing or two.


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From Florida Man headlines to unique guests, one of a kind bracket tournaments or their quirky segments, you’ll find yourself yelling, laughing and possibly learning a thing or two.




My Wife Shows Off Pepperoni Nipples at Yoga - Ep. 108

Chase goes on yet another vacation forcing the guys to call Chris in from the bullpen. The boys tackle some pressing questions like, should you invite friends to do things even if you know they can’t go?, How do lobsters pee on each other?, and is there anything wrong with showing your pepperoni nipples during your yoga class? The guys also kick off the Best 90’s Video Game Bracket with #1 Mario Kart 64 vs #32 Spyro The Dragon and #16 Star Fox 64 vs #17 Roller Coaster Tycoon. Sprinkle in...


Shower Sex or Shower Shits? - Ep. 107

Happy New Years everyone! Cup to Cup is back after a brief break to prepare for season 3 and they are back with a bang. Opening items drop a scary statistic that is truly mind blowing. The new name that sound segment is introduced and the guys are not good at it. Be sure to check it out because listeners have a chance to win our "Shit happens, its Florida" coffee mug, if they are the first to correctly guess the sound by DM'n the podcast. The always hilarious Florida man is back and so is...


Season 3 Trailer

In 2018 the community was hit with a bombshell. 3 white guys, a brown dude and Chris…. created Cup to Cup, the comedy podcast. No one saw it coming, not their friends, partners or even their mothers… Now with another season on the way, the community might just lose their shit when the dudes come back for more… Ok, sorry, enough of this dramatic shit! Season 3 is here and its gonna be a wild ride. The boys return with a new bracket (The Best 90s Video Game), 2 new segments (Whats that...


What's on Tap | Main and Six Brewing

The award winning head brewer and Co-founder of Main and Six Brewing, Dennis Espinosa joins the crew to discuss recent awards, why he'd want Arnold Schwarzenegger as a drinking partner and a "bad review" on our infamous segment, Haters gonna' Hate. Check out Main and Six in Jacksonville, Florida and say whats up! Follow Main and Sex @mainandsixbrewing *What's on Tap Rundown* Lonely Island Haters Gonna' Hateminute Drinking Buddiesminute Beer Triviaminute - Use code...


The 2020 Christmas Episode (Live)

It’s the holiday season which means the crew decided to go live for our third annual Christmas episode. A packed episode with plenty of holiday spirit (especially Chase who yelled the entire episode). Florida Man takes us to Kevin’s backyard of Pensacola and the guys try to finish the popular Christmas songs they picked. BREAKING NEWS! The crew reveals what the next bracket will be and like the previous one it’s full of nostalgia. Chris presents a Christmas Would You Rather and Jose does...


Tell Your Wife Her Downstairs Carpet is Gross - Ep. 105

The guys play rotating host again as Chris sits in for Chase. The guys remember their wildest Christmas parties and Florida man teaches us a fool proof way to evade the police. What If is back to find out how selfish we all could really be and the guys spend 7(ish) minutes in heaven to relive their worst college football memories. The guys fill in the blank and say some nasty things about their wives. Overrated Christmas movies, stupid gifts for your exes and gets wasted. All this wrapped...


Is it Racist? - Ep. 104

Christmas season is finally here according to Kevin and with it comes more ridiculousness from the cup to cup crew. Chris drops a 100 million dollar question to start the show to get the guys fatty brains thinking. Kevin and Jason argue over if gift cards are acceptable presents. Chris adds in the first “I don’t get” in over 25 episodes and we discover Chase’s premium only fans and what he uses his proceeds on. The gang discusses gas station sushi and Jason tries to finally get a “correct...


Trainer Patrick Henigan | Holiday Diets “F*ck Monday, Plan on Sunday” - Ep. 103

We made it to December and Jason is hyped that Christmas is 24 days away. Jose fills in for Chase since he is on vacation traveling in the mountains as the crew welcomes back friend of the podcast Patrick Henigan from Jax Fitness Academy. He joins the crew for the first time since Episode 24. Florida Man takes us to Fort Lauderdale and Patrick chats with the guys about his gym and some fitness tips to help us out during the holidays. 7 Minutes in Heaven dives into the best fictional...


BYOG: Bring Your Own Gravy - Ep. 102

Is Turkey overrated? Is gravy on the top of the Thanksgiving food chain? These are the questions that got the boys going on this Pre-Thanksgiving episode. This week’s menu includes, another horny Florida Man, Seven Minutes in Heaven, a killer Name That Show, delicious Fill in The Blanks, and a huge serving of Trivia! Sit back and relax because you’re going to gobble this one right up! Cheers! *The Cup to Cup Rundown* Florida Man Name that Show 7 Minutes in Heaven This is Where We...


Kevin (Snakeaholic) Pavlidis | Snakes on a Podcast - Ep. 101

Get these motherfucking snakes out of these motherfucking Everglades….and onto the podcast. Legendary snake catcher Kevin Pavlidis aka Snakeaholic comes on the podcast and blows everyone’s mind with his stories of his adventures including his record breaking python catch. Jason turns himself into a Florida man multiple times, Chris gives the gang a historical what if, and Kev wraps up with a Dad tip. You won’t want to miss this legendary episode. Follow our Snakeaholic on Instagram...


The Crew Goes Live for the Big 100

Almost two years to the day the crew hit a major milestone. We dropped Episode 100 and decided to go live on Facebook and YouTube for this milestone moment. Kevin does some serious math for his fun fact and the crew tells us which TV show cast would save them if they were kidnapped. Florida Man takes us down to Key West this week. We also tease new segments for season 3 which includes Name That Sound and who is leading on “The Board.” We have to debate one of the most infamous arguments...


American Ninja Warrior RJ Roman | Flying Squirrels & Ninjas - Ep. 99

With one episode to go until the big 100, they guys invited a real (America) Ninja Warrior to the podcast. RJ Roman took a break from crushing obstacle courses to hang out with the guys and talk everything from his workout routine to flying squirrels. Someone’s board will earn a point after a spooky Name that Show. and Kev gets excited about getting his daughter on a new career path. Jose calls out another week of fuck ups and we wrap it up with a ghostly Would You Rather. Cheers! Follow...


Blow Jobs & Halloween - Ep. 98

Halloween is coming up so of course the crew had to give us a spooky weird episode. The crew starts by giving us an answer to what memory they would want to relive and the answers are….interesting. Florida man is strange as always will someone get on the board? Jason brings up a moral dilemma on 7 minutes in heaven and we find out how far the guys are willing to go for some fame. Fill in the blank gives us the most overrated horror movies and who the crew would like to be trained by. Sit...


The Best 80s Action Movie is... - Ep. 97

It took all summer and part of the fall but we made it to the FINALS of our Best 80s Action Movie Bracket. Our movie expert and producer Chris joins the crew for this episode. Florida Man takes us to The Villages for the first time and it gets dirty. We find out who wins the Best 80s Action Movie Bracket between #5 Die Hard and #18 The Running Man. PJ from 80s Forever and Ever drops their breakdown as well as the crew’s decisions and social media and our boy Henderbeard. Jose couldn’t make...


Drinking the Kool-Aid - Ep. 96

Kevin is back! The little guy is back with the crew for some classic cup to cup tomfoolery. We kick it off with a Florida man story that doesn’t include Florida or a man. Our buddy Bates joins 7 Minutes in Heaven but not before a grown man struggles to say Guyana. Kev tries out a new strategy on Name that Show, Jose tortures us with another This is Where We Fucked Up. Would you Rather leads Jason to randomly read a list of short celebrities. Kevin defends his hero Tom Cruise and we put a...


Derrick Levasseur | Big Brother - Ep. 95

This week’s episode has a very special guest as Big Brother season 16 winner Derrick Levasseur joins the show. Derrick tells the guys about his many projects including a consulting/investigation firm, multiple tv shows, his book, writing a movie script and of course his big brother days. The guys (Chase and Chris) geek out on big brother and ask every question they have ever wanted to ask and Jason tries to help.... The movie bracket is narrowed down to the finals will it be Running Man or...


Riding Alligators & Cypress Knees - Ep. 94

We are getting closer and closer to the episode century mark. The crew brings the energy to kick off the episode (it must be Kevin’s shirt). We visit Miami for Florida Man and either Chase or Kevin gets another point on the board. We start the Final Four of our Best 80s Action Movie Bracket as #16 Road House goes against #5 Die Hard. Does Road House have another upset left? The guys bring on our buddy Thomas to 7 Minutes to Heaven to talk about the FSU vs. Miami rivalry and we discuss...


WWE "Writer" Danny Solo | Allegedly - Ep. 93

Get excited for a weird one, folks. Alleged guest, “Danny Solo”... or “Polo”.. who may or may not “write for WWE” and his creepy but mesmerizing EDM glow mask joined the boys. We get a not so Florida man, Florida man. We also allegedly dive into the final elite 8 match up for our 80’s Action Movie Bracket as #14 Indiana Jones and the Raiders of the Lost Ark takes on Kevin’s baby, #22 Top Gun. Outrageous claims are made on 7 Minutes in Heaven, Jose is totally forgotten (sorta), and we cap it...


Sexual Fetishes - Ep. 92

The guys are back together again after Kevin’s brief hiatus and they make up for lost time. A wide variety of topics is covered including an Ambassador to Aliens, Odell Beckham Jr’s fetish, and witches. Kevin’s uncle cousin’s uncle Chester comes back for a 7 minutes in heaven encore and he doesn’t disappoint. Kevin tries to catch up in points by attempting to win Florida Man or Name that show. Angry Chase returns for another rant that he is positive everyone will agree with... *The Cup...


Artist Josh Phares | The Return of the Artist - Episode 91

The bad ass artist and low key motivator returns to the podcast. The best artist in the 904 Josh Phares joins the show for a second time. We also get Chris coming out of the bullpen to fill in for Kevin as he celebrates his anniversary with his beautiful wife, Erica. Josh and the crew are psyched for being Void Magazine’s top artist and podcast in the 904. They hated Chris’ fun fact and Florida Man takes us to Alligator Point. Josh tells us about what he’s been up to since he was last on...