Eastbound & Down cast and character guide: Who plays whom in the HBO sports comedy flick

When Eastbound & Down premiered on HBO in 2009, it immediately stood out as one of the boldest comedies on television. The show follows Kenny Powers, a washed-up Major League Baseball pitcher whose ego, foul mouth, and endless wrong decisions send him from stadium lights back to his hometown of Shelby, North Carolina.

Danny McBride plays Kenny with an over-the-top bravado that made the character unforgettable, but the supporting cast turned the story into something more than a one-man showcase. Steve Little’s Stevie Janowski quickly became the awkward but fiercely loyal sidekick. Katy Mixon’s April Buchanon, Kenny’s high school sweetheart, provides both conflict and chemistry in equal measure.

John Hawkes stepped in as Kenny’s brother Dustin, often grounding the chaos, while Jennifer Irwin as Cassie gave the family dynamic a sharper edge. Across the series, new faces like Michael Peña as team owner Sebastian Cisneros and Ana de la Reguera as Vida expanded the show’s world during Kenny’s Mexican baseball arc.

Ken Marino, Matthew McConaughey, and Ike Barinholtz added memorable guest roles later. Each actor contributed to the show’s blend of sports comedy and personal disaster, ensuring the cast list became just as iconic as the outlandish storylines.

Eastbound & Down cast and characters

The strength of Eastbound & Down comes from how deep its cast list goes beyond Kenny Powers and his closest circle. Each season introduced figures who shaped Kenny’s journey, and HBO filled those parts with actors who knew how to leave an impression.

Ben Best played Clegg, Kenny’s old drinking buddy and a reminder of the small-town habits Kenny never really outgrew. Andy Daly appeared as Terrence Cutler, April’s fiancé and later boss, who became a roadblock in Kenny’s attempts to pull April back into his chaotic orbit. Elizabeth De Razzo joined as Maria Janowski, Stevie’s eventual wife, bringing a brash presence that matched his awkward energy.

Season two expanded the scope when Kenny landed in Mexico. Michael Peña took Sebastian Cisneros' role, the slick owner of the Charros baseball team, while Ana de la Reguera played Vida, a love interest who challenged Kenny’s usual behavior.

Marco Rodríguez portrayed Roger Hernandez, management's part, trying to control Kenny’s career. Efren Ramirez, best known from Napoleon Dynamite, appeared as Catuey, a player who added more color to Kenny’s time south of the border.

Later Eastbound & Down seasons pulled in familiar comedy names. Ken Marino portrayed Guy Young, a retired athlete turned TV host who drew Kenny into the world of sports entertainment. Matthew McConaughey briefly appeared as Roy McDaniel, a scout evaluating Kenny’s potential comeback. Ike Barinholtz stepped in as Ivan Dochenko, a cocky Russian pitcher who stood as a direct rival.

Tim Heidecker showed up as Gene, part of Kenny’s bizarre ventures in the final season. Bo Mitchell played Wayne Powers, Kenny’s son, adding a family dimension that clashed with Kenny’s reckless nature. Ethan Alexander McGee played Dustin Jr., Kenny’s nephew, who was often caught in the middle of family arguments.

These characters, even in limited screen time, were never throwaways. Each one forced Kenny to face different sides of himself, whether through rivalry, romance, or family. The casting choices kept the show unpredictable, as no guest star felt like a filler presence. HBO gave McBride’s comedy the right support system by filling out every corner of Kenny Powers’ world with actors who could stand toe-to-toe with his larger-than-life persona.

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