The 10 Most Heartbreaking Classic Rock Songs Of The ’60s

The 1960s is often remembered as the decade that offered a cornucopia of classic rock songs – from psychedelia to surf rock to folk rock and blues rock. But the second era of rock ‘n roll also gave us some of the saddest music of all time. Let’s check them out:

J. Frank Wilson and the Cavaliers – Last Kiss (1964)

Originally recorded by Wayne Cochran, J. Frank Wilson and the Cavaliers covered it a few years later. It’s a tragic song about a guy who takes his girlfriend out on his father’s car. As he tried to avoid a stalled car up ahead, he lost control of the vehicle and crashed. His girlfriend died as a result of the accident. It’s actually based on a true story of 16-year old Jeanette Clark and J.L. Hancock whose car hit a tractor-trailer in Georgia.

The Beatles – She’s Leaving Home (1967)

Paul McCartney was inspired to write this after reading about 17-year old Melanie Coe who went missing. Her father told the papers, “I cannot imagine why she should run away. She has everything here.” However, for the rest of the song, McCartney simply invented the events such as when she “meet a man from the motor trade”. Melanie Coe returned home a few days later but it wasn’t until she was in her 20s when she found out the song was about her.

The Doors – The End (1967)

The song is equal parts terrifying and tragic. It’s about death although frontman Jim Morrison initially wrote the words about his breakup with his then-girlfriend. The End evolved during their live performances. Morrison explained that it “started out as a simple goodbye song” but that “it’s sufficiently complex and universal in its imagery that it could be almost anything you want it to be.”

The Velvet Underground – Pale Blue Eyes (1969)

This was reportedly about Lou Reed’s first love, Shelley Albin who was married to another man at the time. Reed once said that they wanted to “had to demonstrate the other side of us” because they didn’t want to be regarded as “one-dimensional.” And with this song, they did just that. Unlike their previous songs which were loud and violent, this one’s somewhat intimate.

The Kingston Trio – Seasons in the Sun (1964)Remove featured image

It’s about a dying man bidding farewell to his loved ones. The Kingston Trio were the first to record an English version of the song but it was Terry Jacks and Westlife who turned it into hits.

The Beach Boys – I Wasn’t Made For These Times (1966)

One of the last songs they finished for the masterpiece Pet Sounds, the lyrics deal with the disillusionment of someone who’s trying to fit into society. Written by Brian Wilson and Tony Asher, Wilson admitted that it reflects his life. He explained, “I did Pet Sounds and all my friends thought I was crazy to do it.”

Creedence Clearwater Revival – Graveyard Train (1969)

The song touches on love and death. John Fogerty sings about “On the highway, thirty people lost their lives”. Fogerty recalled that during recording, it was “very awkward” because it was just him “and the mike in the darkness.”

The Guess Who – These Eyes (1969)

It took Randy Bachman 15 minutes to write the song when he got together with Burton Cummings to complete it. Initially, the band didn’t want to record it because it was a complete departure from their usual hard rock style. They eventually relented and These Eyes became one of their biggest hits.

The Moody Blues – Nights in White Satin (1967)

Justin Hayward wrote this when he was just 19 years old and he revealed to the Daily Express Saturday that it “was quite autobiographical.” He admitted, “It was a very emotional time as I was at the end of one big love affair and the start of another. A lot of that came out in the song.” While there are several interpretations from listeners, most agreed that it’s about yearning.

The Zombies – She’s Not There (1964)

The Zombies’ debut single and their biggest hit, it’s about the narrator’s dissatisfaction with someone who’s not worthy of his trust.