Sad Cover Songs That Stand the Test of Time

The following three powerfully sad cover songs stand the test of time.

I. “This Woman’s Work” by Kate Bush 

First featured in She’s Having a Baby (1988), it’s heard when Jake (Kevin Bacon) is learning that his wife (Elizabeth McGovern) and their unborn baby are in crisis. “As the song plays, we see a montage sequence of flashbacks showing the couple in happier times, intercut with shots of him waiting for news of Elizabeth and their baby’s condition. Bush wrote the song specifically for the sequence, writing from a man’s (Jake’s) viewpoint and matching the words to the visuals which had already been filmed” (KateBushEncyclopedia).

Jen Chaney, Vulture: “Unlike other songs that suffer from pop-cultural overuse — like ‘Hallelujah,’ in all its incarnations — this gut puncher about trying to summon strength in a moment of profound weakness never loses its power. Instead, it has accumulated additional, profound layers of meaning.”

Lyrics from the middle:

…I should be crying, but I just can’t let it show
I should be hoping, but I can’t stop thinking

Of all the things I should’ve said,
That I never said
All the things we should’ve done,
That we never did
All the things I should’ve given,
But I didn’t…

Official video:

When it comes to sad cover songs, Maxwell‘s 1997 more “definitive version” (secondhandsongs.com) of “This Woman’s Work” reigns. He opens below with giving due credit to Bush, though:

II. “Dance with My Father” by  Luther Vandross (1951-2005)

Vandross’s father died when he was eight. This song, however, seems to strike a chord with anyone who’s lost someone. Final lyrics:

…If I could steal one final glanceOne final stepOne final dance with himI’d play a song that would never ever end‘Cause I’d love, love, loveTo dance with my father again
Sometimes I’d listen outside her doorAnd I’d hear how mama would cry for himI’d pray for her even more than meI’d pray for her even more than me…

In 2011 Jacob Lusk (now with a group called Gabriels) blew the American Idol audience away with this cover:

III. “It’s Quiet Uptown” from Hamilton

Lin-Manuel Miranda‘s “Hamilton Mixtape” album features one of the best sad cover songs I’ve ever heard. It’s by Kelly Clarkson, and it doesn’t need the context of the play (the death of the son of Alexander Hamilton and wife Eliza) to be appreciated.

…The Hamiltons move uptownAnd learn to live with the unimaginable
I spend hours in the gardenI walk alone to the storeAnd it’s quiet uptownI never liked the quiet before…
…They are trying to do the unimaginable
There are moments that the words don’t reachThere is a grace too powerful to nameWe push away what we can never understandWe push away the unimaginable…

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