A generation of sell-outs: how the Grateful Dead inspired Don Henley to write a classic

The music we listen to is often a reflection of our attitudes. However, times change, and as times change, so do we. So, does the music we love come with us or stay in the past with that previous version of ourselves? It’s a tricky prospect to consider, and one that Don Henley decided to explore on his track ‘The Boys of Summer’, a layered song inspired by the Grateful Dead, the passing of time and a $21,000 Cadillac.

When the Eagles went on hiatus, Don Henley was keen to continue making music as a solo artist and, in doing so, explored complicated themes that were both a reflection of the world around him and also introspective. When you consider the sound Eagles had, despite being a band in the 1970s, the sound of the ‘60s still lingered, and the complication that the ‘60s generation brought forward filled Henley’s mind when he was writing his debut solo album. 

Henley never spoke too fondly about his fellow person when he was making his debut studio album. The album title, Building the Perfect Beast, he said, refers to the fact that humankind is savage. “We’re the only animal who supposedly has the power to think and reason, but we still act like uncivilised animals. In fact, we act worse. We treat each other worse than animals treat each other.”

That negative attitude towards people carried on into the songs on the record, specifically the hit, ‘The Boys of Summer’. Henley said it was about the Woodstock generation in the ‘60s and that those who lived through that generation still try to act like they preach love and peace but do the opposite. He found the best reflection of this came when he saw an expensive Cadillac with a Grateful Dead bumper sticker on it.

When he was in traffic one day, a Cadillac worth about $21,000 pulled up in front of him with a Deadhead sticker on it. Henley said that this perfectly reflected the mindset of many people from the ‘60s, in that they still preached their hippie ideologies while driving Cadillacs. Essentially, Henley is saying that his generation had sold out by the 1960s.

The piece is a metaphor in that sense. While the lyrics are about an older man dating a younger woman, Henley is actually referring to the ‘60s generation living in the ‘80s. “It is, in the song, sort of an older guy talking to a younger girl,” said Henley, “But at the end of the song, it’s more of a political-sociological statement.” 

Inspiration can come from funny places; love and hate are typical starting points, but what ignites those emotions can vary massively. For instance, with Henley, seeing a sticker on a car was enough to trigger negative feelings that he then used to write music. While the sentiment at the heart of the track is somewhat sad, there is no escaping the piece, which is a classic.

Listen to ‘The Boys of Summer’ below.

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