The Saddest Music, Part 5

22. Judy Garland, “Have Yourself a Merry Little Christmas” (1944)



“Someday soon we all will be together
If the fates allow
Until then, we’ll have to muddle through somehow”

Upset by their father’s plans to move the family from Missouri to New York City, a young Judy Garland cheers her five-year-old sister on Christmas Eve with this song in the classic 1944 musical Meet Me In St. Louis. Now a Christmas standard, Garland and the film’s director Vincente Minnelli asked songwriter Hugh Martin to revise the original lyrics, which they found too bleak. The version that appears in the film represents a middle ground between the depressing first draft and the further-revised, sunnier version that Frank Sinatra would later make famous. With its sweet, wistful melody and mixture of hope and trepidation about the future, no song has better captured the mix of joy and melancholy that defines the year-end holiday for so many. JT

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23. Strawberry Switchblade, “Since Yesterday” (1984)



A minor British hit from the 1980s electropop era, “Since Yesterday” is actually pretty peppy-sounding, until you listen to the lyrics. It’s a Trojan horse of sad. PI

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24. The Notorious B.I.G., “Suicidal Thoughts” (1994)



You’d think suicide notes from poets would be creative; from Virginia Woolf to Kurt Cobain, they’re often as blunt as any layperson’s. Christopher Wallace’s eerily languid downward spiral has traces of humour (B.I.G. on heaven: “Hangin’ with the goodie-goodies, loungin’ in paradise / Fuck that shit, I wanna tote guns and shoot dice”), but his self-loathing is too melodramatic — artless, even — to be anything but sincere: “I’m glad I’m dead, a worthless fuckin’ buddah head.” That he was killed by someone else’s hand is irrelevant. His death wish defined both his art and his life, and if someone else hadn’t done him in, he would have got around to it eventually. DM

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25. “Somewhere Out There” (from An American Tail, 1986)



Jewish-Russian refugee mice have feelings, too. PI

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26. Eric Clapton, “Tears in Heaven” (1992)



“Would you hold my hand / if I saw you in heaven?”

Because, purely in technical terms, you can’t get much sadder than a song about a four-year-old child falling out of a skyscraper window. PI

Bonus Link: “Sorrow is the key that gets our tears out of eye jail.” Mr Show vs. “Tears in Heaven.”

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27. Phil Collins, “Against All Odds” (1984)



This short writeup of “Against All Odds,” by Freaky Trigger and Pitchfork contributor Tom Ewing, is so perfectly pitched, we’d rather just keep our traps shut and direct you straight to the link. That said, the video above — featuring Phil Collins singing through an Aztec mask — doesn’t exactly do wonders for the song’s pathos. PI

Next: The Smiths (finally), and Jordan Timm on the difference betwen “sad” and “miserable”