Same here with file(1) version 5.22 from the Debian jessie package repo. I'd be interested to know in which versions this kind of thing actually works.
My first guess would be "the MacOS one", since from what I have heard, MacOS tends to have older (sometimes much older) versions of basic system utilities. I don't have a MacOS machine nearby to check, so this is just a guess.
At least any terminal escape sequence can be executed if you run `file` on a JPEG, it seems, since this:
Results in red text on my terminal for me.(It also results in file writing a 0xff 0xdb to the terminal, which the terminal turns into the unicode fallback character since it's not valid text…)