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 Luke Benward as TBD Kristine Leahy as Herself Josh Casaubon as Eric Kevin Burkhardt as Himself Co Starring Jeff Witzke as Reporter #1 Alex Marshall-Brown as Reporter #2 Alexandra Fatovich as Delilah Ashley Olds as Agent #2 Ellen D. Williams as Producer Dalen Carlson as Agent #1