Cry Baby Cry: The 5 Saddest Beatles Songs

Has there ever been a better delivery system for pure joy than the music of The Beatles? When they focused their songwriting, vocal, and instrumental powers on an upbeat, positive message, they could elicit smiles like nobody else.

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But we also have to acknowledge that these guys could also do a 180 and have us wallowing in our sorrows when they put their minds to it. With that in mind, here are our choices for the five saddest songs in their catalog.

“Hey, You’ve Got to Hide Your Love Away” from Help! (1965)

The Beatles’ early music owed a debt to several major influences: Buddy Holly, Chuck Berry, Motown artists. But in the years 1964 and 1965, one notable influence started to muscle out almost everybody else, and that was Bob Dylan. In particular, John Lennon saw the artistic possibilities in Dylan’s confessional style, and wrote several downcast songs along those lines. The pinnacle of those was “Hey, You’ve Got to Hide Your Love Away.” It tells the story of a guy who believes burying his feelings is better than experiencing them and suffering the pain that goes with them.

“Yesterday” from Help! (1965)

The package in which this song was delivered has always drawn the most attention from those who think and write about these things. Indeed, the idea to divorce “Yesterday” from a typical rock-band arrangement and let Paul McCartney sing it with only a string quartet at his disposal was a stroke of brilliance. But let’s not sleep on the fact McCartney wrote an amazing song here. Even though the lyrics came to him after the fact, he was extremely clever with them. Instead of wasting time on how we got to this point, he focuses on the depths of his narrator’s sorrow, which only amplifies its impact.

“Eleanor Rigby” from Revolver (1966)

Let’s start by saying there’s always been some dispute as to who contributed what to this song in its structure and writing, so we won’t do too much attributing here. Let’s just call it a group effort and marvel at the genius of the construction. The lyrics of “Eleanor Rigby” offer quick but telling character sketches, while the refrain (Ah, look at all the lonely people) sort of gives us the overarching headline. Finally, the idea to connect these two aggrieved souls when it’s too late for them to benefit from each other’s company is a devastating dagger of a plot twist.

“She’s Leaving Home” from Sgt. Pepper’s Lonely Hearts Club Band (1967)

The story goes the real-life runaway who inspired this Lennon-McCartney stunner, upon hearing the song, was amazed at how The Beatles had seemed to glimpse her inner life. That’s quite the bit of insight on their part. But it’s important to note this song also stands out because it tells the story of the parents as well. Instead of making them monsters, John and Paul made sure to emphasize the sorrow of these folks, even while acknowledging the mistakes they might have made. Throw in that heaving sob of a melody, and you’ve got a monumentally affecting sad song.

“Golden Slumbers” from Abbey Road (1969)

Hear us out on this one, because on its own, “Golden Slumbers” might not seem all that sad to you. After all, it’s just a little snippet of a thing that’s part of a much bigger piece of music, and it might not seem all that different from any lullaby. But you have to remember what this song represents. It’s Paul McCartney’s tacit omission The Beatles’ musical journey together was coming to an end. Hence, the line Once there was a way to get back homeward, implying that the moment to get back, so to speak, had long since passed. This lullaby was essentially putting the greatest band of all time to bed.

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