Guest Stars Billy Eichner as Craig Middlebrooks Sam Elliott as Ron Dunn Aubyn Philabaum as Dana Jeff Tweedy as Scott Tanner Scott Michael Morgan as Skipper Bo Burnham as Chipp McCapp Michael Rothhaar as Terrence Montreaux Shel Rasten as Xander Teresa Reilly as Kitty Goodbye Tyler Nunes as Kevin Rod McCary as Judge Reinletgo