Gambling for Shoes

NFL Weak Two 12.09.2024 26:03 ↓

Jack turns a friend into a gambler even after discussing the destructive nature of betting.

Griffin Returns! 27.10.2023 1:10:32 ↓

Jack is joined by Griffin to handicap football games and circumcision.

First Guest! 20.10.2023 1:00:58 ↓

Jack brings on a friend who is trying to gamble his way to Vietnam.

Heating Up or Melting Down? 13.10.2023 16:16 ↓

Jack basks in a winning record, then takes a clinical look at gambling disorders.

Hotepisode 05.10.2023 13:57 ↓

Jack summons the gambling gods from a Double Tree hotel room.

The R-Word is Back 27.02.2023 24:09 ↓

Jack explores the world of romance novels, covers banned words in stand-up and shares a dark Disney prediction.

If Alexa was Bob 20.02.2023 24:34 ↓

Jack tries to cancel robots, recalls his only radio appearance, and shares another joke!

Bye Bye Football 13.02.2023 24:27 ↓

Jack decides the NFL is now WWE, breezes through UFO news, and cancels Michelob Ultra. Plus a new stand-up clip!

Souper Bowl 06.02.2023 33:56 ↓

Jack spitballs some Super Bowl betting ideas, bemoans the upcoming offseason, then offers a reckless take on Wolrd War.

Pain 30.01.2023 24:24 ↓

Jack copes with football heartbreak, workshops a Patrick Mahomes impersonation, and shares a clip of him provoking a room full of Chiefs fans.

Still Punching 12.11.2022 20:10 ↓

Jack digs deep for a new gambling strategy, then dusts off his political science degree to spread misinformation.

Enemies! 04.11.2022 26:34 ↓

Jack finally hits some NFL paydirt, tip-toes arond Kanye and Kyrie, and meets his first Chicago foe.

Ouch! 27.10.2022 27:59 ↓

Jack weeps over a horrific week 7, gets mad at Dusty Baker's hands, and is suddenly optomistic about social media.

Winning Season 22.10.2022 19:16 ↓

Jack's making NFL guarantees then relives some baseball glory and reviews about a week of stand-up.

Opinions! 14.10.2022 25:50 ↓

Jack picks his favorite NFL teams to gamble on and favorite stand-up comics to watch in this circular reasoning extraordinaire!

Rehabilitated 07.10.2022 21:52 ↓

After a week in gambling jail, Jack returns to prove he's a changed man and ready to make smart picks.

2017 Caracas Tough Mudder 23.09.2022 25:49 ↓

Jack licks his wounds after a brutal week 2, compares Chicago to Venezuela, and attempts to get vulnerable about comedy. Plus fooh-ball!

I told you, God! 15.09.2022 27:21 ↓

Jack toasts himself over a Week 1 victory, denounces sneakerhead culture, and tells his first Chicago train story. Plus shoes!

Who's the bad guy, now? 10.09.2022 24:23 ↓

The podcast returns! Jack talks strategy against street criminals, tells his first Chicago comedy story, and predicts the future for Week 1 of NFL fooh-ball.