When you’ve got the show-stopping, high-volume charisma of Danny McBride turbo charging his performance of Kenny “F*ckin'” Powers, it’s easy to overlook the rather impressive list of guest stars Eastbound & Down featured over the course of its four seasons (which you can watch on HBO Go and HBO Now). From sitcom stars to Hollywood heavyweights, the show’s relentless in-your-face tone has allowed for its guest stars to give their most hilarious, exaggerated, and over-the-top performances.
Here, we take a look at some of those who were able to match the intensity of Kenny Powers whenever they were on screen, from friendly rivals to former teammates.
Will Ferrell – Ashley Schaeffer
“I thought Ashley Schaeffer was gonna be a woman,” says Kenny Powers when he first meets the shifty owner of a BMW dealership. “I love women, and I consider that a compliment,” Will Ferrell’s self-satisfied character responds, with a kind of soft-spoken Foghorn Leghorn accent. Despite their somewhat cordial beginning, Schaeffer and Powers will tax each other multiple times throughout the show’s run, but Schaeffer’s racist, “Old South” attitudes eventually come back to beat the crap out of him.
Craig Robinson – Reg Mackworthy
The man whose home run ended Kenny’s pitching career in the Major Leagues, Kenny’s rivalry with Reg is quick to reignite once he shows up at a promotional event, all thanks to Ashley Schaeffer’s malicious plan to drive up BMW sales. This isn’t a one-off appearance for Reg, either, but it sure is a one-out appearance for his eye, thanks to a Kenny Powers special.
Lily Tomlin – Tammy Powers
When Kenny Powers’ mom is introduced, it’s clear that the apple doesn’t fall far from the tree. From her profanity-ridden rant when her bowling frame is interrupted to her encyclopedia-like knowledge of the effects of various pills when taken together, it’s clear where Kenny gets it from.
Matthew McConaughey – Roy McDaniel
A talent scout from Texas who comes to Mexico to give Kenny his big chance to work his way back up to the big leagues, eventually, anyway. He has a calm, straight-forward approach to his job (just like McConaughey does when he’s selling us all Lincolns), and it turns out to be a rather graphic rendition of prayer, which includes him encouraging Kenny to “suck his dream’s dick.”
Adam Scott – Pat Anderson
Like a lot of people Kenny meets, Pat’s the kind of guy to insert himself into a situation and start making jokes about someone’s dead father. Once that’s out of the way, he introduces himself as the assistant to the assistant coach of Tampa, explaining that their franchise is in need of a “shot of personality.” Once Kenny confirms that all his racist, homophobic slurs are still a part of who he is, Pat happily agrees to sign him.
Don Johnson – Eduardo Sanchez Powers
Spending much of the second season in Mexico, Kenny eventually finds himself meeting his ATV-loving father, Eduardo Sanchez. Immediately, the two quickly brag about their respective wealth and success, from Kenny’s investments in stocks, bonds and famous works of art to Eduardo’s hole-digging, which he does to hide all of his income.
Ken Marino – Guy Young
While Kenny is trying to enjoy life in the suburbs, posing for photos with demanding rental car customers, he crosses paths with his old teammate Guy Young, who brings Kenny on his popular sports talk TV show, only to eventually use it as an opportunity to humiliate him. As the two find themselves pitted against one another, it leads to the greatest water jetpack-wearing stare-downs of all-time.
Jillian Leigh Bell – Dixie
One of the show’s more subdued performances, the characters of Gene and his controlling wife Dixie remind Kenny what he’s in for when resigning his life to the suburbs. Or, from their perspective, a perfectly nice couple wallowing in perpetual misery that also have to put up with April’s crass and unpleasant husband, Kenny.
Ike Barinholtz – Ivan Dochenko
Kenny really, really did not like Ivan Dochenko, a young, Russian-born pitcher who’s star is rising. For all these reasons, including him being Russian, Kenny makes it clear to Ivan that he is his enemy, despite them both playing for the Myrtle Beach Mermen.
Jason Sudeikis – Shane
Kenny’s hard-partying former teammate and best friend. Together, he and Shane make non-stop Top Gun references, all while Kenny tries to hide his insecurity about the upcoming game from him. After all, they’re friends, not someone he “tells sh*t to.” Once Kenny eventually blows it on the mound, he and Shane take solace in some “monster rails” of cocaine, where the lifestyle starts to catch up to one of them — all to the tune of The Bangles’ “Walk Like an Egyptian.”
Sudeikis also appears as Cole, Shane’s more straight-laced brother.
Sacha Baron Cohen – Ronnie Thelman
If there’s anything bad to say about Sacha Baron Cohen’s performance, it’s that he doesn’t appear until the show’s final episode. As the comfortably amoral head of the network, he shows up to Kenny’s show after his meltdown during the Christmas Special, looking to make a few drastic changes to capitalize on his star’s irate personality.
Lindsay Lohan & Alexander Skarsgard – Shayna and Toby
In the show’s rambling epilogue, with Kenny Powers writing his own life story years into the future, Lohan and Skarsgard show up as his fully grown children. Skarsgard’s performance, in particular, is effective, thanks mostly to his facial expressions, which is helpful because they’re both completely silent performances.
Honorary Mention: Seth Rogen – Guy at the bar
After proving himself to be an obnoxious jerk when hitting on a girl in a bar, he follows her out to the street, where he offers her a heartfelt apology, just before being run over by a truck. While Rogen didn’t get the chance to steal a scene from KP, Powers does get to steal the deceased’s job as the closer for Texas due to the accident.