Jason Pettus’s review published on Letterboxd :
2017 movie viewings, #63. At first when I was watching 1968's Chitty Chitty Bang Bang the other night, for the first time since I was a little kid, I simply couldn't understand why this film has ended up mostly fading into obscurity, when similar films from the same period are now regarded as perennial classics: after all, it shares the same pedigree as the others (based on a children's novel by Ian "James Bond" Fleming, with a fantastical adaptation by Roald "Willy Wonka" Dahl, and produced by Albert Broccoli [also of the Bond films]), features the same caliber of cast (which like Mary Poppins stars Dick Van Dyke as a wacky British dude), and contains the same production values (including a musical soundtrack by the Sherman brothers of Mary Poppins fame, and a main setpiece number which features 40 singers, another 40 dancers, and over a hundred trained dogs).
Ah, but then I got into the second half of Chitty Chitty Bang Bang, and suddenly realized why this film languishes so much in the popular lexicon when compared to those other movies; for the story gets really, really screwy and weird about halfway through, with Van Dyke at first extemporaneously making up a story one day about child-stealing pirates so to entertain his kids during an afternoon at the beach, but then somehow that made-up story magically coming true all of a sudden, and with everyone in the cast suddenly in on it and the actions of these made-up characters suddenly having real-world repercussions out in the physical world. Ironically, it would've been fine if the movie had simply presented these absurd events as "actually" happening within this fantastical world (think for example of all the unrealistic stuff Dahl gets away with in Willy Wonka, like flying elevators and dancing orange midgets, a mood he was clearly trying to invoke here as well); but by instead never making it clear whether we're watching "real" events within this children's movie or simply following along with a story the main character is making up in his head as the movie continues, the whole thing feels disjointed and off, making it difficult to get invested in what's happening since there are no real stakes and we're in the middle of a cartoon world where anything can happen.
Now combine this with some questionable choices that the overly cynical Dahl makes here (including making the main villain a black-clad German whose job is to steal children out of the ghetto and perform experiments on them, in a movie that was made only twenty years after the end of World War Two, which apparently was not an unfortunate coincidence but literally Dahl wanting to deliberately evoke the spirit of Josef Mengele in this otherwise sweet family musical); and you're left with a movie whose impressive songs and high production values still isn't enough to save it from being an unsatisfying head-scratcher, pretty much exactly what you would expect if the producers of Willy Wonka had gotten the tone slightly wrong, and essentially the last non-Bond film Broccoli would ever make. Still worth a watch if you've never seen it before, it was nonetheless easy to see here in middle-age why this hasn't become a once-a-year tradition like Wonka, Poppins, and other family musicals from these same years.