1. Steamboat Willie (1928)
One hardly needs an introduction to Steamboat Willie. (If you haven't heard of it, you have been living under a rock for over eighty years.) It was the first cartoon to make heavy and effective use of synchronized sound and Mickey Mouse's (as well as Minnie Mouses's and Pete's) first public appearance. The short received so much acclaim that it was added to the National Film Registry in 1998 due to its historical importance and lasting impact. The title of the short's name is actually a parody of the Buster Keaton film Steamboat Bill Jr. (1928). In Steamboat Willie, like all early Mickey Mouse shorts, Mickey is far more mischievous than his 'tamer' contemporary counterpart, much akin to Oswald the Lucky Rabbit.
2. The Karnival Kid (1929)
Besides having anamorphic hotdogs, Mickey Mouse's 9th cartoon was notable for using actual dialogue. Mickey speaks for the first time, his first lines being, "Hotdogs! Hotdogs!" and, "It's a bum hootch scam keep your money in your pants!" It is up to some debate wether or not Walt Disney voiced Mickey in this short (Walt would voice Mickey regularly up until 1946, when his lungs began too damaged from smoking to allow him do the mouse's squeaky voice.) Mickey's voice is noticeably rougher, causing some to believe he was actually voiced by the famous animation composer Carl Stalling in this cartoon. The scene were where Mickey tips his ear like a hat also inspired Roy Williams to create the iconic Mickey Mouse ears caps.
3. The Skeleton Dance (1929)
The Skeleton Dance was the first Silly Symphony cartoon produced and is widely regarded as one of the series's most memorable. It was animated entirely by Ub Iwerks himself, no small feat considering that drawing realistically proportioned skeletons is quite challenging. (Iwerks was a very fast worker, being able to create 700 drawings in a single day if needed!) This Halloween favorite pokes fun at horror tropes, with skeletons dancing to a foxtrot and yowling cats to boot. Extreme closeups, xylophone music, and atmospheric lighting are used to great effect. Although the The Skeleton Dance does not have much to offer plot wise, all of the creative characters and unique animation make up for it. Scary has never been so funny.
4. Spooks (1931)
Ub Iwerks just had a thing for skeletons and hunted houses. Flip the Frog was a short lived cartoon character, but the second half of his career really had some great shorts. The song that skeleton band plays is called, "Mysterious Mose," and was featured prominently in a Betty Boop cartoon, from the year before, of the same name. Spooks is just as well crafted as The Skeleton Dance, and is a lot more 'scary' and has snapper timing. How many other cartoons would dare to feature a host luring in a cartoon animal to add to his taxidermy collection? Oh, and if the only house you see during a storm appears haunted, I advice you don't spend the night there.
6. The Office Boy (1932)
In this Pre-Hays Code cartoon, Flip seeks work as an office assistant only to run into trouble with a destructive mouse and a sexy, young typist. No doubt due to the influence of ex-Fleischer Bros. animators and the fact that Ub no longer worked for the more conservative Disney, The Office Boy has quite a few gags that certainly weren't meant for children. Flip's cheery disposition does not put him below cutting in front of the other boys in line for the office job. The Great Depression made him quite competitive for employment, especially when cute girls were involved! The audience can probably also relate to Flip, who was blamed for many problems he encountered at work by his unforgiving and stern boss.
7. Room Runners (1932)
Flip the Frog is out of work (again) and attempts to run away from a hotel he owes money to. However, the lady who owns the hotel calls up the police and Flip also has to help a man with a lose tooth and avoid the distraction of a rather scantly clad lady. The result: a lot of mad, slapstick, and politically incorrect insanity! The score for this cartoon is notable as it was done by Carl Stalling, who also composed the music for other Flip cartoons, early Disney cartoons, and later, most famously, for Looney Tunes. It is also interesting to note that Flip does not get the girl at the end of this short. Like quite a few other cartoons by Iwerks, Room Runners does not have a perfect ending for the protagonist, and ends on somewhat of funny, bittersweet note. (Flip gets slapped by the girl and accidentally wrecks the hotel, but gets away from the police and manages to pay the hotel bill.)
8. Funny Face (1932)
Unlike the other Flip cartoons shown here, Funny Face (not to be confused with the Audrey Hepburn movie of the same name) features our hero as a young, lovestruck boy. When Flip is dumped by his (human) girlfriend for another boy, he decides that he needs to disguise himself with a plastic-surgery mask to cover his 'ugly' face. The best gag in the cartoon involves Flip being teased by the masks at Dr. Skinnum's office. Once being insulted, Flip responds back, in song, "Even though I look like heck, you're as ugly as horse's neck!" When Flip saves his girlfriend from a bully, despite losing his mask, he regains his confidence. Looks are not everything after all.
9. Stratos Fear (1933)
Willie Whooper didn't even survive a year as a theatrical cartoon series. However, Willie's outrageous lies about his nonexistent adventures certainly provided an excellent vehicle for inspired animation. In Stratos-fear, Willie's third cartoon, the titular character was redesigned to look less like a boy version of Flip the Frog and to resemble a pudgy, practically ball shaped, over eager child. Stratos-fear, though still very obscure, is the best remembered cartoon of Willie's short lived career. The reason, no doubt, is for the short's outrageous plot (involving Willie hallucinating from laughing gas that he travels to space) and its rather demented animation of numerous bizarre aliens. This makes this short comparable to many of the early Betty Boop and Popeye cartoons in its imagery.
10. Ballon Land (1935)
Was the last cartoon not strange enough for you? Then give this one a try. While most of Iwerks's Comicolor cartoons were rather dull (but lovingly made), a handful of them could be entertaining. The cartoon is basically a cautionary tale about running away from home. When two young ballon kids disobey the warnings of other people in town, they nearly get popped by the menacing Pincushion Man, voiced by Billy Bletcher (best known for his roles as Pete and the Big Bad Wolf at Disney). The cartoon violence in this short is a bit shocking. When the Pincushion Man is accidentally let into town by Ballon Land's foolish gatekeeper, he goes on a violent rampage popping several of the land's residents before he meets his demise. If this cartoon was about actual people, not balloons, it is highly unlikely that so many on screen deaths would have ever made it past the storyboards.
*Bonus: The Multiplane Camera
After making amends with Walt, Iwerks returned to Disney and made several groundbreaking innovations. One of the most memorable was the multiplane camera. This video clip, narrated by Walt himself, explains how the invention works and how it allowed for more realism to enter cartoons. Multiplane cameras were used all the way up until the making of The Little Mermaid (1989), after which digital processes replaced the need for this complex invention. Today, only three of the Disney multiplane cameras survive: one at the Walt Disney Animation Studios in Burbank - California, another at the Walt Disney Museum in San Francisco, and a final one at The Art of Disney Animation exhibit in Disney Land Paris.