Ub Iwerks (his name was Dutch) was an early colleague of Walt Disney's, a prolific animator who was almost single-handedly responsible for such classic works as Steamboat Willie and The Skeleton Dance. But after Iwerks had a falling-out with the boss he struck out on his own, and established a studio under his own name in 1930. There, for the next few years, he and his crew produced dozens of cartoons. The best of them are pretty good, and even the weaker entries always offer a nice moment or two, but Iwerks never recaptured the spark of inspiration that fired his earlier work with Disney, and his studio finally went under in 1936. A chastened Iwerks returned to the Disney factory as a technician and worked there for the rest of his career.
The Headless Horseman was one of a series of "ComiColor" cartoons Iwerks produced, usually based on fairy or folk tales, not unlike Disney's concurrent Silly Symphonies. It's a decent cartoon with both good and bad elements, and serves as an exemplar of the strengths and weaknesses of the overall Iwerks output. On the plus side, the musical score by Carl Stalling (who left Disney's employ alongside Iwerks) is outstanding, extremely catchy and atmospheric, and really carries the viewer along. The color is nice, too, at least in the print I've seen; the Cinecolor process Iwerks was using was cheap, and not as dazzling as Disney's product at the time, but the blues and reds look strong here, and the backgrounds, such as sinister-looking trees against night skies, are especially atmospheric. Iwerks was also experimenting with an early version of the multi-plane camera in this cartoon, a device which would later be used to great effect at the Disney studio in The Old Mill, Pinocchio, etc. The gliding camera movement seen here during the climatic chase is the technical high point. This cartoon has no dialog but there are some amusing visual gags, and for classic era Hollywood buffs there's a cute moment when Katrina imagines her beau Brom Bones as Clark Gable, who is amusingly caricatured.
On the debit side, however, character design in The Headless Horseman is poor. Ichabod Crane is supposed to be ugly, at least he was described as homely in the original Washington Irving story, but everyone else in this cartoon is goofy-looking too, and we start to wonder if that was intentional. More significantly, not one of these characters is the least bit sympathetic, which is important even in a small-scale enterprise such as this one. The viewer has to care what happens to at least one character, or else why watch? We root for Bugs Bunny, we dig Betty Boop, and we might even root for Donald Duck if he isn't being too obnoxious, but there is no one in The Headless Horseman we can even like, much less root for, and this was too often the case in the Iwerks cartoons. Another debit: clownish racial caricatures of black servants, although Iwerks certainly wasn't the only offender in this area at the time.
All in all, sort of a C-plus/B-minus experience, and although Iwerks made better cartoons than this one it's an indication of why he didn't succeed as an independent producer. But Carl Stalling's work is terrific, and he went on to do great things with the Termite Terrace gang at Warner Brothers. And eventually, a very good Headless Horseman cartoon was produced in 1949 -- by Disney, of course!
