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.