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Join the Premium Edition, its on the cheap cheap! Have no fear, the CTC Crew is here to help you shake off the post-holiday weekend blues with a special episode. Kev is out this week but the rest of the guys are here to answer hard-hitting questions like if you had to eat all your meals at one restaurant, where would it be? What's the most Florida …
 
Its sports w/guest Mayor Andy NFL - From worst to last 2022 Edition Ridiculous stats: how does the Yankee's ridiculous start compare to other sports? Whats the first thing you would do if you had a major sports championship trophy accidentally delivered to your house? One Final Stanley Cup Update (Thank you TB) ACC drops the new 3-3-5 mode CuptoCup…
 
Join the Premium Edition, its on the cheap cheap! Episode 172 brings the return of the Colorado kid back from his staycation. We start off with an opening item about what part of your body you would like to upgrade. Florida man for the first time this year takes place in Tallahassee. Was it one of the guys? We get a bracket update as the best potat…
 
Join the Premium Edition, its on the cheap cheap! Who would have guessed that The Colorado Kid is on staycation this week as Chris fills in. The crew opens up talking about which button they would press thanks to “Clayton”. Florida Man takes us to North Port and an angry gator. We give a brief update on our upcoming Chips Bracket. Casual talk about…
 
Join the Premium Edition, its on the cheap cheap! Coming to you from a garage, a closet, and a basement, the boys this week are bringing you all the hard jutting questions. Questions like, If you could win a million dollars but had to sing a song of your choice perfectly, what song would you pick?, and Does Chase have a perfect dick? A Florida Man …
 
Donate to our Island Boy Happy Birthday Wish for Chase Join the Premium Edition, its on the cheap cheap! The boys are back! After a week off to drop their new “true” crime podcast the OG crew is back for episode 169. The episode starts with an opening item of reliving one moment from your past. Kevin goes on a rant about how amazing top gun 2 is an…
 
In the small town of Silentville Michigan young Cynthia Cooper was found washed up on shore of her families lake. The police have ruled it an accident but Jenny Cooper, Cynthia’s cousin, believes there’s a murderer roaming the streets. It’s up to me, Shane Johansson, and the cup to cup team to investigate by interviewing the disturbing suspects inv…
 
Donate to our Island Boy Happy Birthday Wish for Chase Join the Premium Edition, its on the cheap cheap! The crew is having a great day (minus Kevin being bloated). The crew opens up talking how shocked they are Chris just took his first flight and they describe their ultimate nightmare situation. Florida Man takes us to St. Pete involving an angry…
 
Join the Premium Edition, its on the cheap cheap! Episode 167 is here and with it comes the final match up of the most annoying celebrity alive bracket which means the whole crew hops on. Who will win? Cardi B or the Island Boys? Before the match up Chris drops an opening item about what two people you would like to see fight. Jason has a 3 blanked…
 
Join the Premium Edition, its on the cheap cheap! Your favorite guys are back and they’re drinking tequila! The guys discuss what the ideal packed lunch was back in the day and of course one our hosts turns out to be that kid we all hated with the Lunchables every day. Florida Man is back in Florida but this man is on another planet with this headl…
 
Join the Premium Edition, its on the cheap cheap! A busy episode with the crew tonight as they open up talking shots and sex. Florida Man takes us outside Florida to Washington state involving a lady that just needs some rescuing. We start the Final Four of our Most Annoying Celebrity Bracket between The Island Boys and Skip Bayless. The booze kick…
 
Join the Premium Edition, its on the cheap cheap! Episode 164 is here and the Colorado kid is back giving us the OG 3 back together again. The boys jump right in with a discussion that leads to a talk about getting the clap. Chris drops an opening item about spending 30 minutes in a room with a giant spider for 10k. The bracket is here and we choos…
 
We interrupt your weekly scheduled episode with some Kevin & Friends. This time, Chase decided to visit wine country for his 19th scheduled vacation in 2022. Become a premium subscriber! Every dollar supports the crew! This week it's all about educating you, the listener, with information YOU didn't think you needed. Like, lights on or off during s…
 
Join the Premium Edition, its on the cheap cheap! The crew opens up hot debating tank tops and discuss one thing they could relive for the first time which gives us some quality content. The crew reads a couple premium notes and Florida Man takes us to Miami and a rowdy Burger King. We continue our Most Annoying Celebrity Alive Bracket between #2 6…
 
Sports Baby! Opening day in baseball NFL is pushing for flag football to be in the Summer Olympics. Some thoughts from Mayor Adamson: Do you dare agree with The Mayor? Which sport would you like to see added to the Summer Olympics? Also…someone take a peek at the Tournament Challenge and see who ended up winning Cuptocuplife.com…
 
Beer is BACK! We are stoked to bring back Whats on Tap and we did it with a bang with the first brewery thats not in Florida, Wynkoop Brewing out of Denver, Colorado. Todd Bellmyer, the head brewer joins the dudes and KILLED IT. One of the funniest and tech-savvy guys we've had on the podcast. And the episode opens up with an "explosion" Follow the…
 
Join the Premium Edition, its on the cheap cheap! The guys are back with a hilarious one that ranges from people getting stabbed with squirrels to what celebrity Jason would not be okay getting pink eye from. Have you ever gotten an email demanding money to not release your nudes? Jason did and Kev is hoping he doesn’t pay up. The Most Annoying Cel…
 
Join the Premium Edition, its on the cheap cheap! Episode 161 is here and the Colorado kid is not. But fear not because the true person who runs cup to cup fills in Chris! The guys break the ice with a possible haunted house opening item before diving into whether pillows are considered boobs or butt cheeks. This week's bracket match-up leads to he…
 
Be a premium member, your mom likes it! The crew is joined by a close friend and lover of shrimp JC. The crew opens up debating what has divided the internet over the past week. Florida Man takes us to Hernando County with a man just needing some help. The next matchup of our Most Annoying Celebrity Alive Bracket is between #5 Skip Bayless and #12 …
 
Be a premium member, your mom likes it! The Tahiti kid is back from his extended vacation. The guys chat about what kind of restaurant concept they would open and what they’d name it. The Most Annoying Celebrity Bracket continues with this week’s matchup between #3 Machine Gun Kelly vs #14 Jackson Mahomes. We go through your voice nugget, more chan…
 
The most heated we've gotten over sports, ever... Get stoked….The tournament Challenge is coming back! Group will be CUPTOCUPSHOW2022 on ESPN; the group will be live tonight after Selection Sunday (the day you are listening to this) NFL Talk: Calvin Ridley is a dumbass; Rodgers Last Dance sequels; Russell Wilson to the Broncos; MOUNT RUSHMORE IS BA…
 
Be a premium member, your mom likes it! Episode 158 is here and the Tahiti kid Is not. That leaves Chris to fill in as the host which leads to what everyone would expect….a hilarious clusterfuck. The boys start off with an opening item about the most embarrassing way to die. Florida man gives the boys a chance to get on the big board can they guess…
 
Its sports, BABY! Here's some topics we hit on today! Get stoked….The tournament Challenge is coming back! -You get one shot on the basketball court: -Make a Layup: get $50k -Make a Free Throw: get $100k -Top of the Key: get $500k -Wing 3 Pointer: get $750k -Corner 3 Pointer: get $1 million Which one you taking? NFL FA: Where will Saquon Barkley an…
 
Be a premium member, your mom likes it! Jason returns to the show this week as well as “Apple Kevin.” The crew opens up talking about what they would like their wives to wear during sex. Giggity. Our loyal listener Henderbeard gives us some pictures and makes us wonder What Would We Do? Florida Man takes a special visit to Beijing involving the Oly…
 
Sports is back...sorta. What is the weirdest thing in American sports (ex. Why after the SB does the team owner get handed the trophy first?) What athlete meant the most to you as a kid(which athlete did you follow the most and had the biggest impact on you as a kid) If you could take any college player from any previous FSU team and add them to th…
 
There are no rules for this weirdly average episode of Kevin and Friends! Jason finally sat one out and let the rest of the boys steer the ship for once. Kev brought all his special segments like Rapid Fire, Picture Time, and The Real 7 Minutes in Heaven. Yes, we looked at pictures in a podcast. Not to worry, there was bracket time featuring the ne…
 
The OG trio is back for the first time in about a month and it’s glorious. Chris drops an alcohol-related opening item to the shock of no one. Jason drops one of the funniest Floridamans yet can the guys get it? The bracket brings two of the shittiest people in America head to head. Who will move on between Urban Meyer and 6ix9ine. Be a premium mem…
 
You know, the usual...Dancing, Football, Ice Fishing, and sexy Canadians. switch out one Winter Olympics sport for a sport you’d crush at (can be fake af) Make Super Bowl predictions; Talk about some of Mike’s Prop Bets Thanks for listening and always check out CuptoCupLife.com and follow us @cuptocupshow on all the socials! Consider signing up to …
 
Sign Up for our Premium Subscription Here The crew is back and are joined by producer/podcast master Chris. The guys open up discussing how they would spend their magic tokens and Florida Man takes us to Polk County for quite the unique drug bust. We open up our Most Annoying Celebrity Bracket with #1 Jake Paul vs. #16 Nicki Minaj. Embrace the chao…
 
We're back with another "sports" talk episode. Worst incoming hall of Fame class ever? If you could take any fictional sports movie character and add them to your favorite team in that respective sport who would it be? WAY too early Ws and Ls for FSU Football (Kev is hyped) Watch a Football game with any coach (dead or alive) who would you pick? Th…
 
Premium, sexy, beautiful. After Dark. Sign Up! You’re getting an extra idiot for this one folk! Jose joins the guys and they kick it off by talking about what song they would play for their partner's dads the first then they meet them (wrong answers only). Jason brings us a Florida woman who isn’t messing around. We reveal the 16 members of the Mos…
 
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 …
 
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