| Episode credited cast: |
 | Jay Leno | - | Himself - Host |
 | Rickey Minor | - | Himself - Bandleader |
 | Rose Byrne | - | Herself - Guest |
 | Donny Deutsch | - | Himself - Guest |
 | Jennifer Nettles | - | Herself - Musical Guest |
| Rest of cast listed alphabetically: |
 | Erin Andrews | - | Herself (archive footage) |
 | Shannon Benoit | - | Herself - Mother (archive footage) |
 | Steve Byrne | - | Himself - 'Woulda' |
| Kerri Corrado | - | Herself - WJAC (archive footage) |
 | Kathleen Madigan | - | Herself - 'Coulda' |
| Stacie Miller | - | Herself - Spokeswoman, Kissimmee Police Department (archive footage) |
 | Jim Norton | - | Himself - 'Shoulda' |
| Chris Trevino | - | Herself - Neighbor (archive footage) |
 | Wally Wingert | - | Himself - Announcer (voice) |
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