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Premium, sexy, beautiful. All here. Episode 153 is here and with it is a special guest, hilarious comedian Scott Whatley. Scott has the guys cracking up as he tells them all about being a new comedian as dad, where he gets his content and some tips for Kevin's standup debut. The guys discuss what they would do if they could have a bird do anything …
 
Premium, sexy, beautiful. All here. The boys are back together as the “Colorado Kid” Chase makes his return from his new state. The guys open up the show by talking which celebrity birthday party they are attending and we get Jason’s latest random internet finds. The guys debate Kevin’s punishments/bets he must complete for losing and Florida Man t…
 
Premium, sexy, beautiful. All here. Happy New Year folks! It’s season 4 and the boys are back! Well, most of them. The Colorado kid was out but Chris and Jose were in to preview the new bracket and provide the usual ridiculousness. The boys cover what moment of their life they wish they had footage of, where a Florida man hid his stash and of cours…
 
What if a podcast produced by 5 life long friends, came back for their 4th season and disrupted the entire podcast nation? It could happen and it could be this podcast. Enjoy another season with Florida Man headlines, wild games and a bracket subject that will for sure bring controversy, chaos and content thats never been heard before...we think. L…
 
We're back, well Chris is. Enjoy a beautifully choatic drunken read of Twas The Night Before Christmas... and trust me, a lot of shit was stirring tonight. And always, enjoy our premium subscription for dirt cheap here! After Dark, Forgotten episodes and whatever else we want to give you! Merry Christmas, Happy Holidays and Happy New Year from the …
 
Kev and Jason decided to pound a few pints and read you "How the Grinch Stole Christmas" with some soothy Christmas tones. Yep, its that simple but its damn good. Let us know what you think! And always, enjoy our premium subscription for dirt cheap here! After Dark, Forgotten episodes and whatever else we want to give you! Merry Christmas, Happy Ho…
 
Merry Christmas and Happy Holidays you filthy animals! We're back with another live christmas episode, featuring...EVERYONE. So if you've heard a live episode before, its a bit chaotic but its a blast. Scouts honor. Check out the live video here! Everything is Christmas themed, starting with our "secret" word game by Mayor Andy, the opening item, F…
 
Episode 150 is here and with it comes some surprising details about the guys. Chris starts it off with an opening item that has the guys debating the 10 words they would say to their past selves. Jason drops a “Christmas” themed Florida man that stumps the guys. Everybody weighs in for the French fry bracket to decide who guys on to the championshi…
 
It’s not a jam-packed episode this week but we have almost the entire crew (minus Jose) as they open talking about if a comet was coming to end the world and you had one week left to live. Florida Man takes us to Collier County with a frisky couple. Jason has the latest I Don’t Get It involving baby pics. A loaded 7 Minutes in Heaven deals with Cha…
 
Hang on to your giblets folks because we have a jaaaamed packed one for you all this week! The Mayor causes chaos when he introduces “Password”, a new weekly game the guys will play with big implications for the big board. A Florida Man tried to twerk out of trouble and don’t tell Mike from Dadurdays Home Brewing when he can put up his lights! It’s…
 
Episode 147 is here and while Chase isn’t Chris fills in and makes sure to bring the shots. Jason starts it off with an opening item which somehow leads to a discussion of Jason’s grandmother having sex. Florida man stumps the boys per usual but leads to some interesting olympic discussions. The bracket match up is closer than normal will an upset …
 
It’s a jam-packed episode as Jose joins the crew this week. The guys open up talking about escaping a snail and Florida Man takes us down south to Lake County to see if anyone can add to their Big Board totals. We continue the Elite Eight of our Best French Fries Bracket with #4 Arby’s against #5 Checkers. Loyal listeners Naomi and Josh the Artist …
 
This week the boys life’s most pressing questions, Like if you could go back to one decade of your life, which would it be? Is a Florida man from Arizona still a Florida man? And of course, who moves on in this weeks Best French Dry Bracket match up between #2 Five Guys vs #7 Popeyes. Jose throws gives us cheesy one liners and fuck ups before 7 Min…
 
Episode 144 gets extra spooky as Miranda from ghost biker explorations joins the show again for the first time since episode 46. She brings all new spooky stories and shocking ghost encounters. Kevin has a full on ghost boner and Jason is just a little ghost curious. Premium, sexy, beautiful. All here. After Miranda hops off Chris hops on and the g…
 
The crew is back together after another Chase vacation and the guys open up the show placing bets for Squid Game. Florida Man takes us to Gulf Breeze with one creative individual. Chase gets to go through Kevin’s rapid fire questions from last week and we round out the opening round of the bracket between #6 Wendy’s and #11 Burger King. Join the pr…
 
We took a week off from our regular scheduled episode and gave you this bad boy and gave you what you wished for. Kevin & friends. A full episode directed and written by yours truly, Kevin. A lot of random sexy fun. With our boys Jose and Jason of course. If you thought this was good, join our premium subscription. Click here if you're kinda, a lit…
 
Support the boys, even a dollar bro! Join the dark and premium side of things Episode 142 is here and it brings the heat. The guys start off on a tangent about song rip offs leading down a weird rabbit hole. Chris drops an opening item about what movie prop you’d most want to own. Florida man doesn’t disappoint with one of the weirdest charges you’…
 
Support the boys, even a dollar bro! Join the dark and premium side of things Get excited because Chris is joining the OG crew for this one, then get sad at his morbid opening item. It’s spooky season and this weeks Florida man wants you to keep your fake fangs away from his house. The Best French Fry Bracket continues with #3 Chick-fil-A vs #14 Ha…
 
Support the boys, even a dollar bro! Join the dark and premium side of things The crew comes in hot to start the episode as we talk about theme parks with a certain twist. Florida Man takes us to Gainesville to visit an apartment and the guys end up chatting about nature. Loyal listeners Jaime and Josh the Artist drop some voice nuggets. We continu…
 
The guys are back after their brief hiatus and they are coming in hot with the sex, dicks and puke talk. Chris starts them off with an opening item about things we still do from college. Florida man drops an impressive airplane themed feat. The bracket is heated as always who will move on Zaxbys or Popeyes? 7 minutes in heaven brings the football t…
 
Enjoy the return of Whiskey Kev with two special After Dark episodes combined that ONLY our premium subscribers have listened to...until now that is. The first part of this video is what Kevin is narrating btw. Consider supporting the boys by joining our Premium subscription! Click to find out more! CuptoCupLife.com Facebook Instagram Twitter Youtu…
 
Strap in because this one is a trip or should we say bootylicious! Chris joins the guys this week to dive into real hard pressing issues, like why an Arizona woman set her boyfriend on fire and are mom jeans really back? #8 Whataburger takes on #9 Steak N Shake in the Best French Fry Bracket match up this week! The guys breakdown FSU’s upcoming sea…
 
The crew opens up on a different note discussing memorable moments with their fathers. Florida Man takes us down south to Monroe County just looking for some respect. We continue the Best French Fries Bracket and start on the east side of the bracket with #2 Five Guys vs. #15 KFC. Bracket talk gets heated as usual as another restaurant heads to the…
 
Episode 136 is here and the crew is joined by Deeds Bees bee keeper extraordinaire Rebecca Diederick. Rebecca drops bee knowledge bombs and stories all over the place and has the guys cracking up. She tells them all about how her father wraps 10,000 bees around his hand and the time she was stung by over 20 bees in a cheerleading outfit. After Rebe…
 
The full squad loaded up and gave you exactly what you all want…a wild episode with bold claims, angry debates, dirty butt holes and Kev getting Lawyered. The episode starts off with our listeners giving us their best “thrown out of a bar” stories, followed by our bar stories, that leads into a local Jacksonville Florida Man idiot sponsored by our …
 
The crew is back this week after a cursed episode that is lost forever. The guys open up the episode discussing which villain actually had it right and we recap Name That Sound. We get plenty of animal trivia facts and this Florida Man channels his inner Ozzy Osbourne. NEW SHIRTS! Fill in the Blank deals with cities to get drunk in, what you wouldn…
 
We did it. We finally chose our next bracket. All we can say is...it'll be delicious. Check out this very quick announcement and tap the link below to rank the list we have now. Rank Here! If we missed any, you know the drill. Add it at the bottom of the ranking sheet and we'll have some play-in games, if needed. Thank you for your help and you can…
 
We fucked up. We had an audio malfunction with episode 133, its cursed and we are skipping it. But, we do have a dope Story Time episode about DEADLY BALLOONS! If you're not familiar with Story Time, its basically Drunk History with a slight Cup to Cup spin. This drunk story is about deadly balloons in Cleveland, Ohio that happened back in the 80s.…
 
The boys are back from vacation and they brought a guest with them to kick start everything back up! Host of “The Trophy Wife Life” and “The Dirty Little Secrets Club” podcasts, Dayna joined the show brought with her some some spicy secrets. Dayna takes a shot at Florida Man and shares hilarious stories from her show. We bust open some voice nugget…
 
We're coming back in full force Tuesday the 20th from our mini vacations, well not Kevin, he insists it was not a vacation for him... We're also going to start adding some "bloopers" at the end of each episode. (If there are any) So now you have to listen to the wrap up! Special updates! We'll have a guest when we come back and we promise you'll lo…
 
FSU legend and former NFL wide receiver Marvin “Snoop” Minnis joins the boys and absolutely kills it despite a few technical difficulties. He drops FSU knowledge bombs all over the place and brings you back to the FSU dynasty days. He alters his FSU teams with players from different eras and shows the boys how trivia is done. This is an absolute mu…
 
The crew is going on a short break so they made sure to load episode 131 with a ton of great content you aren’t gonna want to miss. Porn is discussed many times throughout the episode leading to the question who exactly is the Martin Scorsese of porn? Support the boys and get naughty by joining our Premium subscription! Chris drops a what if that l…
 
The episode opens with the guys talking about sayings that work in multiple scenarios and lead to some classic banter. Florida Man takes us to Providence, Massachusetts for the first time and the guys spend 7 Minutes in Heaven discussing which athletes would join their dodgeball teams. The sexual talk continues with Jason’s Internet Finds. Support …
 
It’s back to the OG three. The boys share where the last place in the world they would eat is and a Florida Man pepper sprays his mom for the strangest reason. Our buddy from USA Cancer Cycle, Greg Taylor checks in from his 11,000 mile bike ride. Check out usacancercycle.com to learn more and support his cause! Make sure to follow him @usacancercyc…
 
Support the boys and get naughty by joining our Premium subscription! The guys are back and Chris fills in for Chase thanks to Comcast and their shitty internet. The opening item has the guys naming their dicks based on the last movie they watched and there’s some good ones. Florida man doesn’t disappoint and helps Kevin remind Jason of the time he…
 
Time to crack open the Naturdays as the entire crew jumps on this live episode. They open the episode drafting their celebrity flip cup teams before Florida Man sends us to Chris and Chase’s backyard of Tallahassee. The guys are all stumped with the latest Name That Sound. We finally crown the winner of our Best 90s Video Game Bracket as #5 GoldenE…
 
Get ready to be inspired as special guest from across the pond, James Elliott, joins the show to talk about jumping out of planes, mental health, and mindfulness. This bad ass human gave us one of the most interesting conversations we have had on the podcast, you won’t want to miss it. Make sure to follow our boy @jameselliottofficial Join the hott…
 
We have an hilarious special guest join the show, comedian, actor, writer, fashionista, Mr. Dave Hill. He has everyone dying of laughter as he tells stories of his travels and comedy shows. He impresses the gang with his multiple talents including comedy, music, and of course dress making. Don't fuck up, follow him on instagram @MrDaveHill Join the…
 
The episode opens with the crew discussing items they would take into battle and it’s not good. We got some of Jason’s internet discoveries and Florida Man takes us to “Orlando.” We have made it to the Final Four of our Best 90s Video Game Bracket! The first semifinal matchup is between #1 Mario Kart and #5 GoldenEye. Jose brings the big energy and…
 
We have a special one this week as the Cup to Cup wives join us for a special Mother’s Day episode. Before the ladies joined us the guys talked about underrated albums and how Jason has never listened to album in his life. Please consider becoming a premium member to enjoy the many many perks we're including in the subscription! Florida man makes n…
 
Chris opens with a sexual opening item that scrambles the group but its gets even better when Axe throwing Dennis Cejvanovic aka the Bosnian Boy Scout joins the boys. After Kevin butchers his name Dennis proceeds to tell the boys all about how he got into axe throwing, the history of axe throwing opening his own business, and his life as Dennis Smi…
 
The episode begins with chaos and maybe a fire in Jose’s Harlem apartment but Jose is able to join the crew. The crew talk aliens and movies before Florida Man which takes us to Tampa. The crew tries to Name That Sound and we continue the Elite Eight of the Best 90s Video Game Bracket. Mario looks to claim another spot as we have #2 Super Mario Wor…
 
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 …
 
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. …
 
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 Mar…
 
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 …
 
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 …
 
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 commercia…
 
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 t…
 
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 m…
 
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