| Jonathan Frakes | Self - Host |
| J. Kenneth Campbell | Craig Hoffman (segment "The Wall") |
| Kris Kamm | Officer Sams (segment "The Wall") |
| John Billingsley | Simms (segment "The Wall") |
| John Hostetter | Officer McCarthy (segment "The Wall") |
| Gavin I. Glynn | Painter (segment "The Wall") |
| Mariam Parris | Claire (segment "The Chalkboard") |
| Blayne Weaver | Riley (segment "The Chalkboard") |
| Harvey Silver | Eight Ball (segment "The Chalkboard") |
| Judd Trichter | Student (segment "The Chalkboard") |
| Sandy Kenyon | Mr. Mumbles (segment "The Chalkboard") |
| Michelle Hurd | Diane Lerner (segment "The Getaway") |
| Nancy Fish | Mrs. James (segment "The Getaway") |
| Sean Bridgers | Martin Spencer (segment "The Prescription") |
| Don Perry | Everett Spencer (segment "The Prescription") |
| Gloria Dorson | Ruth Fulton (segment "The Prescription") |
| Patricia Place | Harriet Samuals (segment "The Prescription") |
| Adam Wylie | Anthony Shaw (segment "Summer Camp") |
| Thomas Byrd | Richard (segment "Summer Camp") |
| Cody McMains | Darren (segment "Summer Camp") |
| Preston Wamsley | Marty (segment "Summer Camp") |
| Aldis Hodge | Camper #1 (segment "Summer Camp") |
| Edwin Hodge | Camper #2 (segment "Summer Camp") |