Skipper Dan:Feel-Good Or Real Sad?

[Tokusou Sentai Blessranger]

Skipper Dan makes me sad, real sad.

[sataneatscheezwhiz]

Hearing Skipper Dan always cheers me up. The words are kind of sad, I know, but the music and the tune and stuff are great, and it's funny-depressing, not sad-depressing. The misery is so exaggerated that it's funny.

[Edwartica]

I feel like this is almost in the vein of Jonathan Coulton or They Might be Giants. Humorous tones, yes, but deeper than just plain humor. Honestly, I think this might be the most mature weird al song ever made.