Ranking The Times Sh*t Got Real For Kenny Powers On ‘Eastbound And Down’

For all his reckless, insult-driven swagger and overwhelming ego, there was a lot more to Kenny Powers (Danny McBride) than met the eye. Though the show started out as a story about a hotshot young pitcher whose recklessness on and off the mound cost him his career, over the course of four seasons, Eastbound & Down (available to stream anytime on HBO Now) had more than its share of contemplative, bittersweet, or outright heartbreaking moments. Here’s a look at some of those quieter moments that forced Kenny Powers to extinguish the flame of awesomeness and gaze at the smoke to calmly reflect on what it really means to be Kenny f*ckin’ Powers.

8. Selling His Merchandise

The first time we really see a vulnerable side to Kenny is when he tries to earn some money by selling off all his old merchandise on eBay. While Kenny anticipates a bidding war that will drive up the value of his goods and bring a much-needed boost to his ego, he’s forced to deal with the fact that his fanbase just isn’t there anymore, and that he’s become what he was most afraid of: a washed-up former Major League ballplayer.

Having lost both his career and his fame, for the first time we see the real Kenny, the one underneath all that curly-haired braggadocio — a broken-down, insecure man who’s fear that the best part of his life is already behind him is starting to come true.

7. Faking His Own Death

Having spent years fighting his way back to the Major Leagues, Kenny finally gets his wish when he’s offered a job pitching for the Texas Rangers. Once he’s back in the locker room, he gazes at his name next to the number 55 that’s etched above his locker, he hears the sound of his screaming fans throughout the stadium and savors the look of fear in the batter’s eye. For the first time, it seems like everything was really back on track for our hero. That is until he drops the ball right here on the mound and walks away from it all.

Things only got stranger from there. As Kenny drives recklessly down a curvy mountain road, his car veers over a railing and explodes. The real underlying tragedy here is that he walked away with the intention of going back to his family. Which he does, just after he fakes his own death and bleaches his hair for the sake of anonymity.

6. Pat Anderson’s Offer

Just when ol’ KP was starting to feel good about his new life as a schoolteacher, the video of him knocking the eye out of Reg Mackworthy’s (Craig Robinson) head ends up going viral and sports agent Pat Anderson (Adam Scott) literally comes out of nowhere to offer him a job playing ball for Tampa. Suddenly rejuvenated with the thought of returning to the big leagues, his expectations end up crushed to pieces once he learns that Pat wasn’t exactly as big-a-deal as he’d made himself out to be, offering Kenny a job that not only wasn’t his to offer, but a job that wasn’t there in the first place.

5. Betrayed By Aaron

Knowing that he wasn’t going to be playing ball in Tampa, Kenny hides his shame by quietly relocating to Mexico where he tries to give up the one thing he has left: his identity. After getting some cornrows and a couple of new drinking buddies, Kenny becomes a cock-fighting enthusiast and even starts going by Stevie to completely sever himself from his old life. Then, one day, while burying his favorite rooster, he’s betrayed at knifepoint by Aaron (Deep Roy), the man who he’d just deemed his new sidekick. After a series of unprecedented lows, Kenny now finds himself alone in an unfamiliar land with an unfamiliar hairstyle. A sorrowful moment in and of itself, it does lead him back to the pitcher’s mound, which gives Kenny a much-needed silver lining.

4. Reconnecting With April

Showing back up in April’s (Katy Mixon) life after his tenure in Mexico, Kenny persuades her to have a little fun with him, which means some beer-fueled escapades on a putt-putt golf course. After they spend the night slowly falling back in love, Kenny wakes up the next morning alone, left with only a note on the counter from his former lover. Oh, and Toby, the baby they had together.

Even though Kenny had made a real effort to reconnect with April after abandoning her (and the rest of his life), it turns out shotgunning beers and picking fights with random parents wasn’t quite enough to win her back. While his dazed and broken heart is one thing, the fact that he’s suddenly expected to care for his son is daunting. And, frankly, a little terrifying.

3. Abandoning His Son

Here’s one that’s overwrought with disheartening moments. First, after a makeshift family reunion, Kenny finds his father, Eduardo (Don Johnson) sneaking out after scavenging his mother’s (Lily Tomlin) house for valuables in the middle of the night. After the racket wakes up Kenny’s mother, she invites her ex-husband to leave, only to realize that Kenny’s also trying to find a way out. He also wants to leave his infant son in her care in the process. Despite his mother’s assurances that his career in baseball will end, Kenny chooses the path of instant gratification over his own flesh and blood.

If all this weren’t bad enough, the most devastating part is how his mother, weathered from a lifetime of disappointment, just seems to shrug the whole thing off like she was expecting this to all happen anyway.

2. The Ending Montage

In typical Kenny Powers style, the show ends on an extended monologue, with Kenny musing about an unpredictable future; one that’s marked by both tragedy and triumph. Kenny’s steadfast in his optimism, as he finally speaks like a man who’s been changed for the better by the events in his life, an influence that he hopes will be carried on by those who loved him long after his death. Despite this renewed outlook on life, however, we’re left reassured that the wild, reckless Kenny Powers is still alive and well when his narration specifically cues the moment that the audience “goes f*cking apesh*t.”

1. The Death Of Shane

Kenny had a few hangers-on over the years, not to mention the endless devotion of Stevie (Steve Little), but it seemed like the only person who really, truly understood him was his buddy and teammate Shane (Jason Sudeikis). Together, the two were a non-stop party fueled by alcohol and testosterone. One night, mired after losing a ball game, the two decide to kick things up a few notches, and Shane ends up overdosing on cocaine while Kenny dances to a pirated copy of The Bangles’ “Walk Like An Egyptian.” It was a sudden, shocking reminder that Kenny’s lifestyle had real consequences, though that didn’t stop him from crashing Shane’s funeral and hijacking the eulogy while backed by an old Candlebox song.

Even though their old Top Gun argument about who was Goose and who was Maverick was settled, in the end, it left Kenny with one less person in the world who was willing to tolerate him. It’s alright to cry now. This sh*t’s emotional.