- Big Lipped Alligator Moment: For a movie that up until that point had been a slapstick comedy, the Breather Episode when Natalie Wood sings a charming love song by a stream, complete with lyrics and "follow the bouncing ball" animation like a Terry Tunes cartoon short, seems to come completely out of nowhere.
- Canon Sue: Leslie is very much this. Played for Laughs, as the movie is very aware of it.
- Crowning Music of Awesome: For a given value of awesome, but the Great Race (a march as befitting the 1908 setting) was one of the most popular film scores in the orchestral "pops" repertoire until it was displaced by Star Wars.
- Fan-Preferred Couple: Some fans consider Maggie / Professor Fate as having more chemistry than Leslie / Maggie. Probably not helped by how one hilarious scene has her actually kissing the guy. There's actually some Reality Subtext here. Natalie Wood was forced by the studio to do this movie against her wishes, then to make matters worse she was paired up with Tony Curtis. They'd already done two films together and had developed a passionate hatred for each other, so the lack of chemistry between Maggie and Leslie was genuine.
- Ensemble Darkhorse: Professor Fate. Despite Leslie being the hero and the Knight in Shining Armor, Jack Lemmon's villainous, over-the-top, hammy portrayal won the hearts of many. Jack Lemmon even mentioned that he got the most fan mail about the Professor than any other character he ever played.
The Thomas & Friends special:
- Broken Base: Flying Scotsman finally being introduced had a mixed response. While in all versions he cares about his brother Gordon. They kept the Spencer-tradition going that any foreign British locomotive is always depicted negatively. The famous engine's graceful and humble character of the books was rewritten in favor of recasting him as a more pompous and arrogant version of Gordon.
- Ethnic Scrappy: Vinnie is seen as this to some viewers who consider him to be a bad American stereotype, even though his basis is that of a Canadian National U4a 6400 class, built at the Montreal Locomotive Works. The only connection he has to America is the fact that the MLW was the Canadian offshoot of the American Locomotive Co. (AL Co). Muddling things more is the fact that Vinnie is listed as being from North America, not specifically the United States or Canada. In fact, the lack of any new characters truly from the United States was possibly intentional after the Logging Loco controversy.
- They Wasted a Perfectly Good Character: The international engines from The Great Race have all been stated to only be sticking around for this one special, which automatically caused some fans to view them this way.
- This feeling was increased to some following the release of the film in UK cinemas, as with the exceptions of Ashima, Vinnie, and Flying Scotsman, most of them are relegated to primarily background roles, only having one or two lines each with some not speaking at all.