When Becky makes a wish, a cowboy painting on the mural comes to life. His name is Ned Kincaid, and he became great friends with Stacy Jones. No one knows that Ned Kincaid was just a fictional cowboy coming from the mural from many centuries ago. Schemer becomes jealous when no one pays attention to him so he decided to start a train full of passengers in order to impress everybody. Suddenly, the train started to move, so Schemer gets scared and he jumps out. The train is moving at high speed, but there is no driver. Ned Kincaid comes to the rescue and runs after the train on his horse. He manages to jump onto the engine and save everybody from a big accident. By the end of the day, Ned Kincaid disappears back into the painting in the mural. That evening, as Stacy is preparing to lock up, a man who missed his train comes to the station and asks for a ride into town. To her surprise, the man is very simliar to Ned and his family name is also Kincaid; he turns out to be the great-grandson of Ned Kincaid.
- Mr. Conductor
- Stacy Jones
- Billy Twofeathers
- J.B. King
- Midge Smoot
- Ginny Johnson
- Dan Jones
- Kara Cupper
- Mayor Flopdinger
- Ned Kincaid
- Ned Kincaid's Great-grandson
- Lilly's Mother
- Tito Swing
- Tex and Rex
- JJ Silvers
- The Rat Pack
- Schemer's Mother (mentioned)
- Thomas (mentioned)
- Stepney (mentioned)
- Rusty (mentioned)
- Rusty’s driver suggests that an engine is bought to tend to a beautiful part of the railway known as the "Bluebell Railway" (because of the flowers that grow there). Rusty seeks advice from Douglas, remembering how he once saved Oliver from scrap. But Douglas warns him that the only place to find an engine would be on the "Other Railway". Rusty is given permission to go and arrives on the other railway by nightfall where he sneaks past a line of diesels. At last, he finds an engine called Stepney and together they escape, returning to Sir Topham Hatt’s railway where Stepney is restored and put into service on the Bluebell Railway.
- Stepney enjoys his new life working on the Bluebell Railway, but the route is short and he never gets an opportunity to stretch his wheels. So it is arranged for him to spend some time on Sir Topham Hatt’s railway. The engines greet him warmly and he is set to work with Duck, but Thomas begins to show signs of jealousy. The situation is not helped when later that night he is "shunted" to allow Stepney to pass with a special. But when Stepney approaches Thomas with praise, he soon forgets to be jealous.
Jukebox Band Song Segment
- Lonestar Trail Medley
- Buffalo Gals Medley
The Rat Pack Segment Song
- What's New Pussycat?
- Mr. Conductor: Oh dear! Oh dearly, dearly me! But how? The wishing star.
- Mr. Conductor: Well, diary, Becky had made a wish to meet a real cowboy from long ago, and her wish had come true. Now I had Mr. Ned Kincaid from a hundred years ago to worry about. And I wasn't the only one worried...
- Dan: Stepney got what he wanted. He ran the main line.
- Ned Kincaid: So you're telling me that it was magic, the magic that brought me here for a day.
- Mr. Conductor: That's right, Ned. Becky made a wish and it came true. You're it.
- Schemer: It is just that... that you've been paying so much attention to that Mr. Kincaid guy that I thought that maybe if I got a new jukebox or maybe if I learn to drive a train then maybe you would pay attention to me and then maybe you will like me again.
- Stacy: Oh, Schemer, I do like you, not because you learn to drive a train or you have a new jukebox, it's because I know you, because we're friends.
- This is the first televised appearance of the Jukebox Puppet Band's manager, J.J. Silvers. Silver's previously appeared in the direct-to-video release A Day in the Life of The Jukebox Band.
- This is the only appearance of the new jukebox as well as its puppet band, the Rat Pack.
- J.B. King's and Mayor Flopdinger's Founder's Day costumes are similar to Sir Topham Hatt's attire.
- Schemer references Mattel's "Masters of the Universe" line of toys when dressed as Elvis Presley, asking Stacy "What do you think of these wild He-Man type threads?"
- In their founder's day costumes, Ginny bears an uncanny resemblance to Britain's Queen Victoria!
- Washboard Hank guest stars as the One Man Band, albeit, uncredited.
- The outdoor scenes were filmed in the Tottenham, Ontario, Canada area and mostly along the South Simcoe Railway (tourist). The steam locomotive featured in this special is South Simcoe Railway's No. 136, a former Canadian Pacific Railway engine built in 1883 its later seen in Second Chances.
- Though similar to the season 2 and 3 opening credits, the Family Special credits are slightly different. In this version, Mr. Conductor sat on the "Shining Time Station" sign, and does various things on the credits, such as dusting them, balancing on them, etc. It was also used for reruns of seasons 2 and 3 on Fox Family, when the show went away from commercial breaks, and it shows Mr. Conductor sitting on the "Shining Time Station" sign.
- The episodes marks the first of a few things:
- This is the first of the 1995 one-hour family specials. All four specials were broadcast in primetime slots. It is also the first episode to feature Thomas stories from the show's fourth season.
- This special is the final appearance of Mayor Flopdinger.
- The telephone voice of Schemer's mother is actually Stacy and Harry's conversation from Season 1's Promises, Promises.
- This is the first and only time Schemer has verbally interacted with members of the Jukebox Band, via telephone to JJ Silvers.
- The special does not credit who performed as The Rat Pack. It is assumed from the singing voices that they were performed by Alan Semok and or Craig Marin.
- Mr. Conductor tells both stories to Dan, Becky and Kara in this special.
- While the Jukebox Puppet Band dresses up in historic costumes for Founder's Day, when they actually begin performing they suddenly revert back to their normal outfits.
- While Mr. Conductor's whistle and sparkle, as well as the Jukebox background music, sound lower in the other three family specials and Mr. Conductor's Thomas Tales, they still sound the same in this special as it did in Seasons 2 and 3.