Ranking Kenny Powers’ Most Formidable Rivals On ‘Eastbound And Down’

Like any great saga, Kenny Powers faced his share of enemies on his personal journey from cocky fallen athlete to not-completely-terrible-human being-all-of-the-time. Kenny was a hero to no one but himself — and Stevie — and his enemies in many respects weren’t that much worse than him. Still, he took on each of them and emerged victorious in the end.

The spectrum of Kenny Powers’ enemies is a wide one, ranging from passive aggressive former classmates to sadistic car dealership owners. Not all of them were equal and some definitely made Kenny’s life worse than others, but each played their role of nemesis to KP at some point in Eastbound & Down’s four-season run (which you can stream on HBO Now). So, to honor the enemies of Kenny “f*ckin'” Powers, let’s start with his weakest foe and work our way down to his most-hated of enemies.

8. Terrence Cutler

Somewhat insecure and average in every possible way, Terrence Cutler (Andrew Daly), was never a true match for Kenny Powers in terms of popularity. We never see any sort of flashbacks to Kenny and Terrence in their high school days, but it’s a safe bet they weren’t attending the same parties. After Kenny’s fall from grace, though, Terrence not only gets to be Kenny’s boss but he manages to steal his old flame. All of this instantly makes Principal Cutler Kenny’s arch-enemy, even though he shows no ill will towards Kenny, at first… After Kenny steals April away, Principal Cutler does go off the deep end.

7. Sebastian Cisneros

Kenny and Sebastian (Michael Pena) really should have been friends. The two men both enjoyed recklessly spending money and enjoyed deep discussions on the best part of the female anatomy. As the owner of the Charros baseball team, Sebastian was a fan of Kenny’s American style of showboating and wanted to make Kenny his gringo all-star. Once Kenny’s fling, Vida (Ana de la Reguera), met Sebastian and got a whiff of his money, though, it was only a matter of time before Kenny’s business and romantic relationship went up in smoke. Because nothing ruins a budding friendship faster than finding your amigo with his head buried between your woman’s legs.

6. Aaron

Trading Stevie (Steve Little) in for Aaron (Deep Roy) as a new sidekick didn’t exactly work out for Kenny. While he was a lot more intimidating and ruthless than Stevie ever was — despite being two feet shorter — Aaron lacked Stevie’s loyalty. The foul-mouthed Aaron was quick to anger and thought nothing of bullying men twice his size. Kenny probably should have taken note of Aaron’s psychotic personality and steered clear, but he failed to do so and eventually found himself being double-crossed and robbed by Aaron of their cockfighting winnings. Stevie may have been a mostly ineffective sidekick, but the guy never pulled a knife on Kenny.

5. Dontel Benjamin

Loudmouthed bullies tend to only get louder and turn up the obnoxious a-hole behavior when they meet one of their own, which is exactly what Dontel Benjamin (Omar Dorsey) did when Guy Young (Ken Marino) brought Kenny onto Sports Sesh. Not one to give up his role as the show’s “funny guy,” Dontel annihilated Kenny with the sort of insults that would have crushed a man with a less inflated ego. Not one to bow out, Kenny made it his goal to shut Dontel’s “na, na, na,” catchphrase up once and for all and replaced his “whack style” with a new suit and $80,000 green Viper for added confidence. Armed with the support of April and a car he couldn’t afford, Kenny went in for round two of Sports Sesh and took Dontel down for good with a barrage of ruthless and crowd-pleasing insults.

4. Reg Mackworthy

So here’s the thing, if you throw a fastball out of rage and it knocks somebody’s eye out, you’ve likely made an enemy for life. Granted, Reg (Craig Robinson) did egg Kenny on, but the two weren’t exactly on good terms before the whole Ashley Schaeffer BMW ordeal. Two seasons later, when Reg showed up with Schaeffer at Myrtle Beach’s Black Bike week, it was evident that time hadn’t exactly softened the tension between Kenny and Reg, yet despite old wounds, he resisted Schaeffer’s demands that he smash Kenny’s pitching arm in a street fight. Too bad. He might have finished higher on this last had he gone through with it.

3. Ivan Dochenko

Despite being canned from the majors and kicked out of Mexico, Kenny Powers never lost his ego. So when the Myrtle Beach Mermen brought in Ivan (Ike Barinholtz), their young Russian hotshot pitcher, Kenny knew his chances of becoming top dog were in jeopardy. In an effort to sabotage Ivan, Kenny attempted to be his mentor, but the Russian quickly caught on that the Kenny Powers training method wasn’t exactly productive and declared war. Fortunately for Kenny, Ivan wasn’t accustomed to the rowdy, battery-chucking behavior that comes with a drunk stadium full of Rockingham Ruckus fans and he crumbled under the pressure.

2. Guy Young

Dontel might have been the obvious enemy to Kenny Powers on Sports Sesh, but it was Kenny’s ex-Atlanta teammate and Sports Sesh host, Guy Young (Ken Marino) who was the true threat. After Kenny took down Dontel and allowed his ego to once again get the best of him, Guy set out to humiliate Kenny by leaving his mic on when he went to the bathroom, allowing the entire studio audience to hear Kenny’s bathroom mirror pep talk. It was a dirty trick, and only the beginning as Guy later told Kenny at the lake while they enjoyed a leisurely jet pack sesh that he planned to destroy him for good.

Kenny had certainly met more formidable foes in his day, but with his marriage to April on the verge of collapsing, the stakes were high and Kenny found a way to emerge triumphant when he gave Guy a taste of his own hot mic medicine.

1. Ashley Schaeffer

Eastbound & Down’s Ashley Schaeffer (Will Ferrell) might not be the first name to spring to mind when you think of the greatest TV villains, but he certainly deserves an honorable mention. With aviator shades hiding the pure evil in his eyes and Nature Boy Ric Flair hair, Ashley Schaeffer, formerly of Ashley Schaeffer Kia and formerly, formerly Ashley Schaeffer BMW, became Kenny Powers’ greatest enemy. Reg and Kenny might not have liked each other, but it was Schaeffer playing the puppet master and pitting them against each other in the pitching contest that would result in Reg losing an eye.

Returning as a plantation owner who forced Stevie into the humiliating role of Geisha girl only fueled Kenny’s hatred of Schaeffer — and likely lowered his opinion of Stevie even further.

In the end, it would be Reg Mackworthy (and the Grim Creepers) who would defeat Schaeffer after he let fly a string of racist remarks when Reg refused to finish Kenny. A sweet bit of irony that allows Schaeffer to claim the top spot here.