Mysterious cowboy Ned Kincaid arrives at Shining Time Station and instantly builds a bond with Stacy Jones. A jealous Schemer resorts to his old devious ways in an attempt to win over her interest.
| Actor | Role |
|---|---|
 George CarlinMr. Conductor | Mr. Conductor |
 Didi ConnStacy Jones | Stacy Jones |
 Tom JacksonBilly Twofeathers | Billy Twofeathers |
 Erica LuttrellKara Cupper | Kara Cupper |
| AAri MagderDan Jones | Dan Jones |
| DDanielle MarcotBecky | Becky |
| BBrian O'ConnorSchemer | Schemer |
 Ed Begley Jr.Ned Kincaid | Ned Kincaid |
 Jonathan FreemanTito Swing (Voice) | Tito Swing (Voice) |
| OOlga FelgemacherDidi the Drummer (Voice) | Didi the Drummer (Voice) |
| CCraig MarinRex / JJ Silvers (Voice) | Rex / JJ Silvers (Voice) |
| PPeter BairdGrace the Bass (Puppet) | Grace the Bass (Puppet) |
| KKenny MieleGrace the Bass (Puppet) | Grace the Bass (Puppet) |
| AAlan SemokTex (Voice) | Tex (Voice) |
| JJerome DempseyThe Mayor | The Mayor |
 Barbara HamiltonGinny | Ginny |
| MMart HulswitJ.B. King | J.B. King |
| CChantellese KentLilly | Lilly |
 Bobo LewisMidge Smoot | Midge Smoot |
| SSusan StackhouseLilly's Mom | Lilly's Mom |