Special Guest Stars JoAnna Garcia Swisher as Rachel Patrick Jimmy Kimmel as Himself Guest Stars Jack McGee as Buck Garland Bert Belasco as Sonny Evers Ryan Dorsey as Tommy Miller B.J. Britt as Will Baker Katie Nolan as Herself Bob Balaban as Frank Reid Colin Cowherd as Himself C.J. Nitkowski as Himself Jeff Torres as Stubbs Matt Vasgersian as Himself Kristine Leahy as Herself Luke Benward as TBD Josh Casaubon as Eric Kevin Burkhardt as Himself Co Starring Alex Marshall-Brown as Reporter #2 Jeff Witzke as Reporter #1 Alexandra Fatovich as Delilah Ashley Olds as Agent #2 Ellen D. Williams as Producer Dalen Carlson as Agent #1