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 ...

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...

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, hilario...

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 c...

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 ...

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 D...

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 brack...

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*

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.

...

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, st...

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 g...

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 holiday...

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*

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 le...

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 Boar...

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 w...

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 horro...

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 a...

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 ce...