Dumbo was a movie I watched somewhat regularly as a little kid. On the surface, it seems like a nice story about an underdog flying elephant who overcomes his tormentors and becomes a star. With it's bright colors and circus setting, it initially seems like a lighthearted tale. But there's a lot of darkness here. I think Disney does a good job of subtly suggesting at the harsh realities of circus life. The cruelty to animals, the backbreaking labor, and the discrepancy between the public face of the show and actuality of the inner workings.
One of the songs I remember liking best from this movie was the "Song of the Roustabout". I think it was the driving rhythm and the spooky minor key that appealed to me. Also, I thought it was really neat to see how circus tents were built, and I liked that the animals helped.
This is one of the songs that people often point to as proof that Dumbo/Disney is racist. The idea of this scene is not inherently racist. It shows the intense, thankless labor that black people were resigned to. However, some lyrics (specifically "when we get our pay, we throw our pay away") are pretty prejudiced seeming. Basically, this song has nothing on the Crows singing "When I see an Elephant Fly."
The weirdest scene in the movie is when Dumbo and Timothy the Mouse get WASTED.
It's got a trippiness to it that was way ahead of it's time. The part that starts at 1:50 is my favorite, I know all those lyrics by heart. And at 2:08, we get a sweet elephant Voltron, neat!