Oswald the Lucky Rabbit is having a difficult appointment at the dentist one day. The dentist, struggling to yank a tooth out of Oswald's mouth, gives him an anesthetic—in the shape of a blow to the head with a mallet. Oswald is just beginning to come to after this when he hears a news bulletin on the radio.
The radio reports that "Old King Cole has the blues." The king, it seems, is suffering from depression. His court jester has tried to amuse him, but failed. Oswald rides to the rescue, crying out "Old King Cole has the blues! Old King Cole has the blues!" He assembles an all-star cast of Hollywood comedians, who each do their part to cheer Old King Cole up.
- All Just a Dream: The whole Old King Cole story was a dream Oswald has while whacked out in the dentist's chair.
- Aside Glance: Ends with Oswald looking at the camera after the dentist extracts his tooth, only for the roots of the tooth to hook onto Oswald's shoes and yank them off as well.
- Blowing Smoke Rings: Greta Garbo reacts to Oswald's "Old King Cole has the blues!" cry for help by blowing smoke rings and saying lazily, in a thick Swedish accent, "I think I will stay home."
- The Dentist Episode: Oswald visiting the dentist, although the story veers off into completely different territory after a while.
- Gross-Up Close-Up: In the opening, we are treated of the sight of Oswald's teeth, eyelashes and uvula, as he wails in pain from an aching tooth.
- It's Raining Men: Or rather raining birds. One pie flying through the air has "blackbirds" stamped on it. One by one the blackbirds inside crawl out of the crust and parachute away. This is a gag on the old nursery rhyme about "four and twenty blackbirds baked in a pie."
- Pie in the Face: Laurel and Hardy do this to each other and to the king to cheer him up. When Old King Cole flings his pie back at them, he triggers a massive Food Fight.
- Shout-Out: Loaded with shout outs. Among the Hollywood stars drawn in this cartoon: Charlie Chaplin, Harold Lloyd, Buster Keaton, Greta Garbo, The Marx Brothers, Laurel and Hardy, and W.C. Fields, and quite a few more.
- Visual Pun: Oswald has in his lower teeth a bridge and a crown—that is, an actual bridge between teeth and an actual king's crown on a tooth.