Special Guest Stars Dean Winters as Dennis Duffy Jon Bon Jovi as Himself Guest Stars Elizabeth Banks as Avery Jessup Jason Sudeikis as Floyd DeBarber Jon Hamm as Dr. Drew Baird Stewart Steinberg as Old Janitor Maechi Aharanwa as Keisha Folake Olowofoyeku as Jamaican Nurse #2 Horatio Sanz as Maynard Shinnerrie Jackson as Jamaican Nurse #1 Taylor Hanes as William Douglas Rees as Walter Stein Madeleine Rockwitz as Evelyn Uncredited Ashley Wigfield as Foxy Moneybags