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“Eight Miles High” is a song by The Byrds from their 1966 album, Fifth Dimension. It is about a plane journey. This echoes the plane crash that killed Buddy Holly, Richie Valens and The Big Bopper.

Much like “Light My Fire” by The Doors, the use of “high” caused many censors to assume that the song was about drugs and it was widely banned. McLean could be deliberately playing on that meaning, particularly given the mention of “grass”, a slang term for cannabis.

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“Helter Skelter” was a very popular Beatles song.

In 2015, McLean confirmed that this line is a reference to the Manson gang’s infamous murder spree in August 1969. Manson claimed to have been inspired by “Helter Skelter”, which he thought foretold a future where white men would be second-class citizens in the USA.

“Helter Skelter” became so intertwined with the Manson murders that Vincent Bugliosi and Curt Gentry eventually wrote a book on the murders with that title.

This is the song’s most noticeable anachronism – “Helter Skelter” was released in 1968 and the murders took place in 1969, whereas the rest of this verse seems to deal with events of 1966 and 1967.

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Elvis was widely known as the King of Rock and Roll. In 1958, at the peak of his popularity, he was drafted into the army.

When he returned two years later, he started performing ballads, which weren’t as popular with young people. Dylan was more attuned to what was hip, and took the position as the leader of the counter-culture that Elvis had vacated.

McLean refers to this position as a “thorny crown,” an allusion to Jesus, in that this new king is a savior, but also bore a burden: the price of fame and the pressures of being such a symbol of a generation. Dylan faced constant criticism for his decisions, such as “going electric” rather than sticking to acoustic folk.

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Although McLean flips the traditional saying, Buddy Holly’s song “Early In The Morning” contains a similar lyric:

Well, you know a rollin' stone
Don’t gather no moss

Of course, this could easily be referencing The Rolling Stones, “Like A Rolling Stone” by Bob Dylan, or the magazine which takes its name from the song. This lyric therefore serves as a useful bridge between the rock and roll of the 50s and the music and culture of the 60s.

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On February 3rd, 1959, Buddy Holly, Ritchie Valens and J.P. “The Big Bopper” Richardson were killed in a plane crash near Clear Lake, Iowa, together with pilot Roger Peterson.

Holly was one of the biggest names in rock, whilst Richie and The Big Bopper were up-and-coming artists supporting him on tour. The deaths were big news, and made the front pages of newspapers.

When the plane crash happened, McLean was 13 and his job was the neighborhood paper boy, referenced by the lines “With every paper I’d deliver / Bad news on the doorstep.” McLean was as stunned as many of Holly’s fans.

I dedicated the album American Pie to Buddy Holly as well in order to connect the entire statement to Holly in hopes of bringing about an interest in him, which subsequently did occur.
- Don McLean, speaking to Cecil Adams (available here)

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Shooting coca-cola is a reference to both shooting heroin and doing cocaine.

The mention of Coca-Cola earned this song a ban from the BBC for product placement, which is thought to have stopped the single reaching #1.

The Kinks changed Coca Cola to Cherry Cola in the single version of “Lola” when faced with a similar challenge.

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“What’s Gucci?” is a semi-common greeting derived from “what’s good?” ‘Ye just takes this further, including referencing Louis Vuitton. He’s come a long way since the days when he couldn’t pronounce Versace.

The repetition of “what’s…?” creates anaphora, emphasizing this particular segment of the verse

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Aspirin is a painkiller- she talked so much he got a headache.

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MC Hammer was fast on his feet when he danced in U Can’t Touch This, so he’s likely to have gotten blisters.

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The woman Kanye is with isn’t used to the trappings of fame. In a restaurant, she orders familiar fish fillet rather than something sophisticated. She praises a car that Kanye doesn’t hold in particularly high regard. This betrays her humble background.

Kanye tells her to stop being awestruck and act like she normally chills with complete ballers like him.

The same thing happens in episode 4.09 of The Wire.

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