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A comedy debate show based out of Boston Massachusetts. Hosted by Shawn Carter.
Episodes

Jul 16, 2026
Jul 16, 2026
1hr 22 sec
In our return after a 2 year hiatus we're talking about Literature. Most of the questions are inspired by classic books.
Hosted by Shawn Carter and recorded LIVE at the Blue Ridge Comedy Club.
Our comedians debate important questions including:
Most monstrous act by Victor Frankenstein building a creature from parts of corpses and reanimating the almagamation or marrying his own cousin.
Who would you rather have to fight one cat in the hat or 10 llama’s in red pajamas.
Six Wives of Henry the 8th or the 4 Baby Mamas of Elon Musk
If you woke up one day having transformed into a giant insect like Gregor but you were not able to hide in your room. Which job would you rather HAVE to show up for; Pest Control Technician or Waffle House line cook.
More romantic poem “Shall I compare thee to a summer’s day” by William Shakespeare or “Ode to my Socks by Pablo Neruda?
And so much more!!!

Jul 29, 2024
Jul 29, 2024
26 min
This is an episode we recorded on Earth Day. 2023. So it was kind of a lost episode until I just discovered it while searching through old files on my computer.

Apr 18, 2023
Apr 18, 2023
46 min
Host Shawn Carter invites people on-stage to argue the important aspects of their hobbies during this live show recorded in Bristol Tennessee.

Oct 17, 2022
Oct 17, 2022
44 min
This week on Pick a Side Stupid. Shawn Carter and Joe Bridges ask the important questions. Whether you're a fan of comic books or just a fan of arguments, this is the show for you.

Oct 10, 2022
Oct 10, 2022
1hr 9 min
In this episode comedians debate absurd scenarios inspired by music videos.
Shawn Carter hosts this night of friendly disagreement at the Blue Ridge Comedy Club in Bristol Tennessee.

Jun 19, 2022
Jun 19, 2022
51 min
On this episode of the Pick a Side Stupid Podcast we ask our comedians the important questions like "What's the better scented candle: gasoline or fishing bait?" and "Would you rather date someone who whistles all the time or shoplifts sometimes?"
Hosted by Shawn Carter and recorded in Bristol Tennessee.

Feb 19, 2022
Feb 19, 2022
38 min
Spiderman or Squirrel Girl, Batman or Arm Fall Off Boy. This week on the podcast we ask the truly difficult questions.

Feb 2, 2022
Feb 2, 2022
56 min
Host Shawn Carter talks with John Murphy about Christmas trivia, their favorite Christmas movies and why you shouldn't buy an Ostrich.

Dec 16, 2021
Dec 16, 2021
55 min
If you had to have a pet bat would you rather have the kitti's hog-nosed bat (only 30 millimeters) OR a giant golden-crowned flying fox (6 foot wingspan)
Would you rather be in a swimming pool with one great white shark or 100 candiru fish?
Would you rather a partner that mates for life or one that bites your head off immediately after?
All these questions and more will be answered this week on the podcast.

Mar 30, 2021
Mar 30, 2021
34 min
On this week's episode Shawn Carter and Sarah Morgan talk about Dolly Parton movies 9 to 5, Best Little Whorehouse in Texas and Wild Texas Wind as well as their childhood favorites The Last Unicorn and The American Rabbit.
