The girls behind Naruto keep talking about this visiting caravan. Apparently they've got a really good singer. Naruto's never really cared about music, and usually he stays away from girls (he's seen enough of Sasuke's fanclub to be absolutely terrified of girls), but from what they're saying, being a good singer is a really good way to get a ton of attention. And Naruto loves attention.
Naruto went straight home that day to practice his singing.
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-Kurama-
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"NEVER SING AGAIN. You sound like a dying cat getting run over by a truck (no, I don't know what that is either!)! Actually, that doesn't even begin to describe it! Throw the cat off a cliff into a swimming pool, then shove it in a washing machine! That's only HALF as bad as you sound! If you keep going, I swear I'm going to kill everyone and then myself, just to save the world from this torture!
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-Naruto-
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Ok, maybe Naruto wasn't a singer. Still, he was nothing if not opportunistic.
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-Iruka-
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There was supposed to be a test today, but as soon as Iruka started to hand them out Naruto made a sound like a dying walrus. Iruka was (rightly) concerned, only for Naruto to assure him that he was only humming to himself. Iruka was skeptical. There's absolutely no way that a singing voice that horrendous is even possible!
Halfway through the test, Naruto started doing his best impersonation of a piano being thrown around by a tornado. Iruka ran away. The students couldn't agree if Naruto was their new hero or if they should superglue his mouth shut.
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-Naruto-
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Oh, Naruto knew how to use this! He spent the rest of the week "promoting" some of the meaner shop owners by standing outside of them and "singing for the crowds." And when they tried to chase him away, he just climbed to the roof and belted out his song for the whole market to hear!
Business in Konoha took a huge hit that week. The poor Hokage had to ask Naruto to stop, because foreign business and traveling merchants didn't want to come for fear of hearing Naruto singing.
Kurama wasn't sure whether to be impressed or horrified.