A Brief History Of Kenny Powers Ruthlessly Insulting Everyone On ‘Eastbound & Down’

Few TV characters have embodied the definition of “a-hole” more than Kenny Powers. For four seasons covering 29 expletive-laden episodes, Kenny Powers used, abused, and mocked everyone who came into contact with him. It didn’t matter if they were foe or friend, everyone on Eastbound & Down had their fair share of middle fingers and insults hurled their way from Kenny Powers.

Racking up a complete list of every trash talking “f*ck you” moment in the history of Eastbound & Down would be an exercise in futility. But, in celebration of Danny McBride’s birthday (he’s 38), I’ve selected some of Kenny’s standout moments of greatness — with greatness in this context being a man who takes being a douchebag to levels few have ever seen.

(Note: some of the clips I wasn’t able to embed, so just follow the link to watch the insults in action.)

Kenny meets Principal Cutler — season 1

Kenny Powers would never have cared for a man like Principal Cutler to begin with, but once he learns that he’s engaged to his high school sweetheart, April, Cutler becomes a verbal punching bag. Standout insult: “I play real sports, not trying to be the best at exercising.”

“Honey, I love you. I think you’re a terrific girl. But you have clothes like a f*cking dickhead.” — season 1

(Kenny Powers: fashion police here.)

It’s hard to argue with Kenny on this one, after all, he does have a personal stylist picking out his fringe shirts. That trumps shoplifting from the Fashion Bug no matter what the social occasion.

Kenny Powers runs into trouble at the mini golf course — season 3

(Kenny Powers goes off at the Putt-Putt here.)

I’ve spent enough time at Myrtle Beach and Pigeon Forge to know that mini golf brings out the worst in a person. Nobody plays through Kenny’s putt-putt game and they sure don’t tell him he can’t repeatedly say “butthole” at a family-friendly tourist attraction.

Kenny insults the kids — pretty much every season

(Kenny’s P.E. Q&A session with the kids here.)

The fact that Kenny’s an uncle — and later a father — has no weight whatsoever on how he interacts with children. From the very beginning of the series we learn that kids — particularly those that look like Shrek — are fair game for Kenny’s insults.

He’s not the guy you want educating the youth of tomorrow on physical fitness, or coaching an inner city baseball team, or raising a child of his own.

Kenny vs. Ivan — season 3

(Kenny’s season-long feud with Ivan here.)

Next to Ashley Shaffer, Ivan Dochenko might be Kenny Powers’ greatest foe in the series. We only see Ivan — played by the hilarious Ike Barinholtz — for one season, but he’s the one man that threatens to steal Kenny’s thunder with the minor league Mermen. Kenny lets the insults fly the second he meets Ivan, not only insulting Ivan’s athletic skills and homeland, but detailing how he would murder him with a trident and make him into a puppet.

Kenny mushes the doughnuts — season 4

(Methodical doughnut smashing anger here.)

Throughout the series, Kenny struggles to climb back up to his major league superstar status from the dregs of “average joe” life. Mark is just another person getting in Kenny’s way and no amount of goodwill doughnuts is going to change that. Not only does Kenny insult Mark by smashing his doughnuts, but he essentially gives a middle finger to the entire office staff.

Kenny destroys Dontel — season 4

(Watch the smackdown here)

Kenny launches into Sports Sesh bully Dontel Benjamin like a well-trained insult assassin after being made a fool in the previous episode and getting called out by Guy Young. While the blitzkrieg of trash talk would later prove to be Kenny’s downfall by inflating his ego just like all his other victories, his verbal smackdown was one of the final season’s standout moments.