Eastbound and Down: 10 Best Guest Stars

We look at the best superstar teammates that have surrounded Danny McBride's Kenny Powers

Kenny Powers doesn’t need any stinking teammates. Let’s make that clear. Regardless, every now and then an actor pops up on Eastbound and Down to lessen the load that Danny McBride carries solely on his shoulders. Usually, these guest stars fit right into the Eastbound fabric; they’re deluded, self-centered, selfish egomaniacs, perfect fodder for Kenny Powers to play off of. Here we’ve filled out the roster with the best supporting players on the Eastbound team.


10. Matthew McConaughey as Roy McDaniel

For baseball players, there’s no greater rush then stepping out on a field knowing that when the ball is in your hands, all eyes are on you. That feeling is amplified when you’re a journeyman pitcher trying to cling onto a job and the scouts are scribbling on their clipboards after each motion you make. Now imagine the scout who will determine the fate of your career, your livelihood, your the ability to bring home warm food to your growing children, is super hunk Matthew McConaughey. It seems like a nerve-wracking task. But under the bright lights in Mexico, Kenny Powers brushed off his fears and conquered his Mexican adversaries. His reward was a minor league contract hand delivered by Texas Rangers scout Roy McDaniel, a smooth talking Texan who gives Kenny the pep talk of a lifetime. Though he’s likely not in the final season of Eastbound, McConaughey will be back on HBO soon in a new cop drama titled “True Detective.” We can only hope he delivers lines like “Kenny Powers, it’s time to quit tickling balls and start sucking your dream’s dick.”

9. Don Johnson as Eduardo Sanchez 

Don Johnson has seemingly been spending the last decade trying to wipe away all the machismo and heroics of his past life as Crockett on Miami Vice. With roles in Django Unchained and Machete, Johnson’s really been embracing his inner scumbag. His work on Eastbound and Down is no different. As Kenny Powers’ Dad, Eduardo Sanchez, Johnson is truly sleazy, a con man with a taste for women, drugs, and self-delusion. The apple doesn’t fall far from the tree folks. You would think the father and son would hit it off, but they don’t necessarily. The pair reminds me of a more hardcore version of Ricky Bobby and his dad from Talladega Nights. Johnson is just an ace casting by the Eastbound and Down team.

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8. Ike Barinholtz as Ivan Dochenko

Miss MADtv? So do we. Back in the heyday of FOX’s late night comedy, Ike Barinholtz, one of MADtv’s all stars, constantly played sports figures. So naturally Barinholtz and his impressions fit right in when he was cast as Russian flamethrower Ivan Dochenko. His rivalry with Kenny Powers was a heavyweight bout, matching the up and coming Russian stud versus the washed up legend. Sound familiar?  

7. TIE: Adam Scott as Pat Anderson and Deep Roy as Aaron 

Adam Scott only appears in two episodes, but his cameos have defined the direction of the show. The Parks and Recreation actor enters Eastbound and Down with the signature macho bravado he displays in all his roles. Scott plays Pat Anderson, a young, hotshot assistant to the assistant GM of Tampa Bay who walks into Dustin’s backyard with promises of Black Amex cards and oral favors from the Jonas Brothers. Anderson’s promises eventually prove empty when he reveals that he was never authorized to sign Kenny in the first place. It set up the Mexico storyline of season two and the brief, but powerful rehab scene in which Anderson admits he slept with his sponsor’s wife… while his sister watched. Never mind who banged who, Eastbound and Down has always been a story about redemption. Anderson’s final step in his quest for sobriety is to make amends and he does so by bringing the aforementioned Roy McDaniels to Mexico to scout and eventually sign Kenny, leading to season three’s Myrtle Beach storyline. 

Similarly, we wish Deep Roy, who played Kenny’s Mexican sidekick Aaron, could have stuck around a little more. Though Roy is small in stature, his stage presence was enormous. If Kenny became the heart and soul of Mexico, then Aaron was the cock and balls of the whole operation. 

6. Ana De la Reguera as Vida   

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There comes a time in every man’s life when he has to sit down and face the inevitable question: are you a boobs or butt guy? Kenny vehemently contends his affections lie with breasts, at least historically. Who could blame Kenny for being a mammary man with April hanging around the cafeteria? Once Kenny’s journey reached Mexico, he needed a new muse to catch, shoe away and then try to recapture. We assumed it would be another woman who could ably fill out a D cup. Instead, Kenny fell for Vida, a sultry nightclub singer with a booty that could bring out the animal instincts in any man. Mexican born Ana De La Reguera didn’t just bring an incredible singing voice to Eastbound’s second season, but she also portrayed a strong, independent woman who couldn’t just brush aside Kenny’s bullshit. We applaud Vida for that. 

5. Ken Marino as Guy Young

Eastbound’s final season could be a stepping stone for Ken Marino. He’s best known for his role in the critically acclaimed, but sparsely watched Party Down. Currently, Marino is on another hilarious cult hit loaded with comedic talent, Childrens Hospital, that’s unfortunately hidden on Adult Swim. Now with a primo role on a hit HBO series, Mariano has a chance to prove his worth. So far as Kenny’s friend-turned enemy Guy Young, Marino has delivered. Guy Young is a pleaser. He’s Kenny’s egotistical, showboating, ultra-competitive equal. It’s been a pleasure to watch Kenny interact with Guy and create an intense and on-air and off-air rivalry.


4. Craig Robinson as Reg Mackworthy 

At this point, Craig Robinson needs no introduction. Robinson’s Reg Mackworthy is Kenny’s biggest (on-field) rival. He’s a trash talking, money loving, Ashley Shaffer BMW-peddling legend. Even though Kenny knocked his eye out, we have to assume Reg will make an appearance before Eastbound signs off for good. 

3. Michael Pena as Sebastian

Michael Pena brought his offbeat brand of humor to Eastbound and Down as Sebastian, the owner of the Charros. Sebastian is Kenny’s opposite in that he’s strickly an ass man. Though he eventually is caught delivering oral sex to Vida, Sebastian is a believer in Kenny and does what it takes to keep the brash ballplayer happy. Just like Kenny, Sebastian is all talk and that’s fine because we loving hearing these guys run their mouths.

2. Jason Sudeikis as Shane

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Jason Sudeikis is one of the kings of the guest turn. His supporting guest routines on 30 Rock, It’s Always Sunny In Philadelphia, and Children’s Hospital have all been memorable, due in part to Sudeikis’ cool, everyman nature. In Eastbound and Down, he’s the opposite of “cool” and “everyman”; he drives an enormous pickup truck that makes the Batmobile seem subtle, has a staggering alcohol problem, and an obnoxious southern accent. Not surprisingly, Shane is the perfect best friend for Kenny Powers, the catcher to his pitcher. Watching the two embrace and coddle their inner ids together provided comedic gold in Season Three. Unfortunately, Shane lived a little too fast and wound up inside of a coffin by the end of the season, with Candlebox blaring away.

1. Will Ferrell as Ashley Shaffer 

Will Ferrell steals the spotlight in almost everything he’s in. At over six feet tall, with impeccable comedic timing and a gift for improvisation, he’s pretty hard to ignore. He’s even harder to ignore when you give the man flowing, bleach-blonde locks and have him shouting out Ric Flare “Woo!”’s every five minutes. As Ashley Schaffer, Ferrell plays another foil to Kenny Powers, but one that seems even further separated from reality. After ruining a promotion for his car dealership (Ashley Schaffer BMW, WOO), Ferrell is hell bent on destroying Kenny Powers. The most fun aspect of the character is his unpredictability, partly because Ferrell improvises much of his lines. 

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