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