Guest Stars Billy Eichner as Craig Middlebrooks Natalie Morales as Lucy Susan Yeagley as Jessica Wicks Jason Mantzoukas as Dennis Feinstein Brent Briscoe as JJ Keegan-Michael Key as Joe Jorma Taccone as Roscoe Santangelo Josh Groban as Himself Co Starring Richard Lee Burch as Herman Lerpiss Will McLaughlin as Officer Randy Killnose Allan McLeod as Trodd Frankensteip Susan Isaacs as Martha Kamala Jones as Trish Darcy Donavan as Patty Donkonit Michael Daniel Cassady as Devin L. Tourguide Jen Oda as Kiki Adrian Zeigler as DJ Bluntz