This famous duo takes on Cadillac Jack... Do you think he can manage??

Blake Shelton takes on the King Of Pop with Can't Beat Caddy!!

Can Cole bring the heat and take Cadillac Jack down??

Cadillac Jack was so embarrassed that he felt the need to leave the studio because Dallas refused to talk to Charles Esten... Fortunately Charles played along and let Dallas speak with Deacon Claybourne.

Season 2 of The Voice. Team Adam

It's a 3 question pop culture trivia showdown and the list of celebrities who have played is too long to list here... But guess who called Caddy and begged to play Can't Beat Caddy? Gary LeVox of Rascal Flatts!

Have you ever had some bad (or even good) news to break to someone but just couldn't bring yourself to do it? That is exactly what happened to Kicks 101-5 listener Alan. Alan asked Cadillac Jack to help Break The News to his wife Deb about their upcoming beach vacation.

This morning Caddy and Dallas played "Irish I Knew"... The radio version of the game called Heads Up. Guess the word on the card from your partner's clues before time runs out. One listener partnered with Dallas, another listener partner's with Caddy. Whoever gets the most Irish phrases correct in 30 seconds wins Corn Beef OR Cabbage!

We find out who the true King of Pop is when Cadillac Jack challenges Todd Chrisley to a game of Can't Beat Caddy!