This HBO special, based on Rosie O'Donnell's book of the same name, uses animated and live action segments to explore the vital role that humour plays in our lives.
| Actor | Role |
|---|---|
 Rosie O'DonnellBaby Rosie (voice) | Baby Rosie (voice) |
 MadonnaSelf (voice) | Self (voice) |
 Hazelle GoodmanNot listed | Not listed |
 Gilbert GottfriedSelf | Self |
 John LeguizamoSelf / Self - Voice | Self / Self - Voice |
 Jackie MasonSelf / Self - Voice | Self / Self - Voice |
 Mary Tyler MooreSelf (voice) | Self (voice) |
 Chris RockSelf (voice) | Self (voice) |
 Marlo ThomasSelf / Self - Voice | Self / Self - Voice |
 Josh PeckSelf | Self |