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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

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(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

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(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

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(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.