The Crew Goes Live for the Big 100

NOV 9, 2020216 MIN
Cup to Cup | The Comedy Podcast

The Crew Goes Live for the Big 100

NOV 9, 2020216 MIN


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 Board.”


We have to debate one of the most infamous arguments we have had on the podcast. 7 Minutes in Heaven dives into which fictional sport you would play and which environment would you rather play sports in. Jose gives us the top 5 moments we messed up during the first 100 episodes and it’s hilarious. Fill in the Blank has a guest appearance from our boy Henderbeard and it involves celebrity roommates, movie titles, childhood throwbacks and turn ons. 


She’s Always Right is back with a special rapid fire round and we round out the longest episode ever with trivia. You will get plenty of laughs with us and if you play the drinking game, probably just as drunk as we did. Enjoy some throwback voice nuggets and some classic intros as we celebrate reaching 100 episodes and hope the next 100 are just as awesome. Enjoy and as always….Cheers!


*The Cup to Cup Rundown*


  • Florida Man @ 12 minute 


  • What's that Sound (Beta) @ 24 minute


  • 7 Minutes in Heaven @ 54 minute


  • This is Where We Fucked Up @ 74 minute


  • Fill in the Blank  @ 99 minute


  • She's Always Right @ 171 minute


  • Trivia @ 189 minute - Use code "cuptocup" to save yourself 20% off and get FREE shipping.


Thanks for listening and supporting us! Please subscribe, drop us a review and share us to a friend. Seriously, tell a stranger!


As always, check out for merch, updated brackets, to drop a voice nugget, blogs and more.



Email the podcast if you want to be a guest or sponsor an episode!