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“Two-Headed Boy” is an example of Jeff Mangum’s brilliant writing on Neutral Milk Hotel’s sophomore album "In the Aeroplane Over the Sea".

The lyrics most directly alludes to Anne Frank’s isolation while in hiding from the Nazis, though, in the form of allegory, it can also be said to carry across Mangum’s growing feeling of regret after the success of Neutral Milk Hotel. However, Mangum’s writing deliberately allows for many interpretations, such as the “two-headed boy” being a literal boy, a figurative one, or even a cassette tape.

The song is very simple compared to the rest of the album, featuring only Magnum’s powerful vocals and simple acoustic chords. Despite this, it is remembered as one of the best examples of Mangum’s eclectic and cryptic lyrics and unique storytelling.

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