Second and final two shorts to portray Mickey with buck teeth.
When Mickey is preparing intensely to swing his club, the soundtrack plays a snippet of the 1936 swing standard Sing Sing Sing. The song's composer Louis Prima starred as King Louie of the Monkeys in The Jungle Book (1967), one of the final films which Walt Disney was personally involved in.
"Canine Caddy" from 1941 is fully featured in the 22nd episode of the second season in "Disneyland" "On Vacation (1956)", also titled "On Vacation with Mickey Mouse and Friends" on video releases, which aired on March 7th, 1956.
"Canine Caddy" from 1941 got it's own adaption in the 1941 July issue of "Good Housekeeping" magazine, where Mickey wants to show how it's done, and says he'll make a "hole in one", with Caddy Pluto already holding the flagstick, while waiting for the "hole in one". Mickey drives too long; he putts too short; The ball sails east and west. It simply won't roll in the cup, and Mickey is distressed. Determined Mickey tries again and again, and always misses, with weary Caddy Pluto thinking he can't stand much more of this. While Poor Mickey wonders what to do, Pluto gets the idea of making one hole as big as all eighteen, while looking very happy and having a sparkling golden golf ball (instead of a typical glowing lamp, when an idea sparks) next to his had. Then Pluto digs the big hole, puts the flagstick in, and lays on the dug up pile of dirt next to the hole, and wags his tail, while happily looking tired but also proud. Mickey then suddenly looks to Pluto and tosses his golf club and hat to the side, while having a surprised reaction and ends with the text "So be like Mickey--don't give up In any work or play Because some unexpected help Will often save the day." Mickey's design mostly stays true to this look in the Cartoon, the only difference is that his hat is in a golden yellow color, instead of his light blue hat from the Cartoon, or his red/brown ish and green striped square-shaped slightly green-tinted hat from the Poster. His shoes might also be slightly brighter, than in the Cartoon. Pluto has a green collar, instead of a red one, like in the Cartoon and on the Poster. The flag's color is pink, has a yellow "I" on it, and has a yellow pole, while in the Cartoon the flag is instead red, bears a slightly yellow-tinted "K-9" on it it and is held by a brown pole. In both the Cartoon and the adaption, the pencil bag Pluto wears matches Mickey's shoe colors distinctly in each of them.
"Canine Caddy" from 1941 is the second and final Cartoon where Mickey has buck teeth, the first was the 1941 Mickey Mouse Cartoon "The Little Whirlwind (1941)", which established unique short-lived redesigns for Mickey and Minnie including the changes of a slimmer body, perspective ears and a bigger head, hands and feet as well as the absence of a tail, which Mickey still had in his usual red shorts until the next Cartoon "A Gentleman's Gentleman (1941)", where he is shown laying in bed, so it wouldn't be seen anyways, and in "Canine Caddy" from 1941 it is first seen in effect. Part of the redesign was that Mickey was also given buck teeth (Minnie apparently also got this addition, although it was never shown in any Cartoon), which were only shown in "The Little Whirlwind" from 1941, when Mickey was whistling, and for the second and final time in "Canine Caddy" from 1941, where it is shown three times in total, though not while whistling, but while talking, when he takes a hit. The buck teeth were only shown in these two Cartoons and the overall unique short-lived Designs would last until the 1946 Mickey Mouse Cartoon "Squatter's Rights (1946)".