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Episode 177 is here and co-host vacation Chase is not as he’s on his 10000th vacation of the year. Jose and Chris fill in and seeing as this was recorded on IPA day they made sure to take that seriously and get as drunk as possible. Chris drops an opening item of what is classy when you’re rich and trashy when you’re poor. Jason gives a Florida man…
 
The crew jumps right into our Best Chips Bracket. Plenty of discussion for the matchups this week which are #2 Lay’s Original vs. #31 Lay’s Dill Pickle and #15 Spicy Sweet Chili Doritos vs. #18 Sun Chips (original). This bracket will gets us heated so we spend all of our time voting on these matchups, Cheers to loyal listeners Henderbeard, Josh the…
 
This week the boys bring the energy that only an opening match-up episode of a new bracket can! Before breaking down some chips, the boy broke down super powers and a Florida woman had a strange strategy to selling a kid's toy. Think twice and subscribe to our premium content! Click here. The guys break down the first two bracket matchups of the Be…
 
Episode 175 is here and with it comes the entire OG crew. Chason teams up on Kevin causing him to ask the guys, not to “Mansplain” things to him. Chris starts the episode with an opening item about the maddest you have ever been. Can Kevin or Chase get on the big board with Florida man? Loyal listener Antonio drops an I don’t get that most the guys…
 
The OG crew is back as Kevin returns from his week off. The guys open up this week giving each other stripper names which gives us some hilarious conversation. Florida Man takes us to Duval County and a man is “defending himself.” A quick bracket update as we break a record for most submissions leading up to this bracket. Chris gives the crew the l…
 
Its Sports! - Pick one QB that would overachieve and one QB that will underperform in 2022 - Name a city that doesn’t have an NFL, NBA, MLB or NHL team that most deserves one - If you could build a dream starting rotation of any 5 pitchers in MLB history, who are you picking? CuptoCupLife.com
 
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 …
 
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