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Cup to Cup | The Comedy Podcast

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Florida Man meets dad life with interactive games, tournament brackets & wild guests - You’ll yell, laugh, bitch & possibly learn a thing or two!

Florida Man meets dad life with interactive games, tournament brackets & wild guests - You’ll yell, laugh, bitch & possibly learn a thing or two!


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Florida Man meets dad life with interactive games, tournament brackets & wild guests - You’ll yell, laugh, bitch & possibly learn a thing or two!




Livin' off Waffles, Red Bull & Life (Vaca Kev)

Nothing can ruin Vacay Kev’s vibe on this episode, not even some really passive aggressive notes left by an petty neighbor or a very loco Florida “doctor”. We listen to your sexy submissions for “Cup to Cup, After Dark” and the guys bring us closer to the Best 90’s Video Game Bracket Final four with #1 Mario Kart vs #9 Tony Hawk. As always, please consider becoming a premium member and supporting the crew. We've already released so much exclusive content! Click here to learn more! Jose...


Bukake, Butt Cakes, & Jason giving HJs

We did a thing. We created a membership page. Sign up to become a CTC Premium Member, hand us a couple of dollars and we give you a ton of content and hugs. For more details on joining the squad, click here If you'd like to drop a one time donation, do it here Thank you guys! This week the cup to cup crew gives us one of the wildest episodes ever. Chris starts it off with a video game related opening item before Jason gives one of the more unbelievable Florida mans yet. Before jumping...


Streamer SuperNin10Bros - Nintendo Lab Nostalgia

The crew relive their early drinking days and then welcome special guest Twitch streamer Raji aka SuperNin10Bros. Florida Man takes us to Orange County. Raji educates us on the world of Twitch and live-streaming and his awesome basement setup which we are all jealous of. He also helps us with the bracket matchups for this week. We have #4 Super Mario 64 vs. #20 TMNT: Turtles in Time and #21 Madden 64 vs #5 GoldenEye. Name that Show returns as the guys try to get another point on the board....


Double Dicked Kev, Part 2

The boys are back solo for episode 117 and one of our co-host is having a rough day...cough it’s Kevin... but we’re sure you already knew that. After a tasty opening item they guys get into a Florida Man that resulted in a Florida eunuch. Am I an Asshole explores if it’s okay to take legal action against your significant other. The Best 90’s Video Game continues with #2 Super Mario World vs #18 NFL Blitz and #10 Street Fighter II vs #7 Zelda: Ocarina of Time. Jose tells us Where We Fucked...


What's on Tap : Ology Brewing

Ology Brewing likes to describe their brewery as an experimental brewery and they aren't joking. Nick Walker, the head brewer and owner of Ology Brewing Co. has taken his skills from working with Grandfather and Father in biology labs and converted them into brewing beer. Nick tells us about his insanely cool history with craft beer, psychobiology and the study of taste and smell and how that has influenced his beer. Don't worry, Nick kills it during Drinking buddies and Lonely Island too....


Storm Chaser Mike Obinski - Dust Storms, Hail & Tornados

Episode 116 welcomes another amazing guest, storm chaser and photographer Mike Obinski joins the crew. Mike tells the crew all about his tornado, dust storm, and typhoon adventures through out the mid west. Jason goobs out on his many credits for his incredible shots of storms including being used in Thor 2 and dozens of documentaries and commercials. Follow mike @Mikeolbinski After Mike hops off Kev turns his rage on as he gets heated over this weeks bracket matchups. Kevin then channels...


Ice Climber Will Gadd | Being a Red Bull Athlete

The crew welcomes Will Gadd to the show. Will is a Red Bull athlete, climber and overall badass. Florida Man takes us down to the Wendy’s in Jupiter and Will takes very little time letting us know his thoughts on Florida (good stuff). Will blows our mind when he tells us all about how he started climbing, how cold it can get, how he became one of the first Red Bull Athletes and all of his insane adventures. Follow Will Gadd Here Then we round out the first round of the bracket with #11...


Herpes Got Me Out Of A Speeding Ticket

The crew wastes no time getting right into it in this one. Jason takes a quick trip down memory lane and tells us about the time an itchy crotch saved him from getting a ticket, a brand new Florida man takes us to Oklahoma and Name That Sound makes its return to the rundown. The boys get heated and a little confused while breaking down this weeks matchup of our Best 90s Video Game Bracket. This week we’ve got #12 Zelda: Link’s Awakening vs #21 Madden 64 and #5 Golden-Eye vs #28 Gran...


Things in Porn That Piss Kev Off

Alcohol was flowing in this episode and it made for some truly wild side convos. Florida man doesn’t disappoint in what may be the most petty segment yet. The guys take a tangent talking about sex noises and Kevin’s possible new segment “what about porn makes me angry”. Will there be another upset on the 90’s video game bracket or will the top seeds move on? Jason makes two promises that he will most likely regret if the listeners step up and make it happen. She’s always right and are you...


Cyclist Greg Taylor | Cycling the United States

The crew welcomes Cyclist Greg Taylor to the podcast. Greg is cycling around the country for six months from Jacksonville, Florida and all the donations made are going towards cancer research. Greg tells us all about his idea and training for this challenge which starts on February 20th. Florida Man takes us down to Tampa and we continue our Best 90s Video Game Bracket with Super Mario 64 vs Aladdin and NBA Jam vs TMNT: Turtles in Time. Fill in the Blank involves life, running and sex. We...


Kev Gets Controversial

The guys go through some of your Florida man birthdays before another edition of Florida Man and they are GREAT. We power up another round of our Best 90s Video Game Bracket with #10 Street Fighter II vs #23 The Simpsons and #7 Zelda: Ocarina of Time vs #26 Doom and yes, Kev has all the sound effects for you. A special edition of “Am I an Asshole” looks at one of our own hosts controversial thoughts. Top that off with a new This is Where We Fuck Up, Voice Nuggets and the return of Trivia,...


Shark Expert Dickie Chivell | Fighting Off Great Whites with a Broomstick

The legend and risk taking shark expert Dickie Chivell joins the crew and Jason and Kev get giddy like a bunch of school girls. Known for his unique and brilliant studies on Discovery Channels Shark Week, Dickie Chivell joins the group from South Africa and has no problem fitting right in. Dickie jumps right into our Florida man segment and takes one for the team when we present him a Would You Rather. Dickie tells amazing, hilarious, and all around mind blowing stories and facts about...


Olympian Kareem Maddox | Tokyo 2020 Olympics? - Ep. 109

Chase decided to come back from Montana and rejoin the show as the crew welcomes Olympic basketball player Kareem Maddox to the show. Florida Man takes us to Jason’s backyard in Duval and we find out more about gold medal winning guest Kareem and his story and his FIBA career. The first Fill in the Blank of the season involves being kidnapped, olympic sports and fictional athletes. The guys spend 7+ minutes discussing the NFL conference championships. We continue the first round of the...


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...