1. “Have Yourself a Merry Little Christmas”
Also known as the saddest Christmas song of all time. It’s mildly hopeful, sure, but it’s mostly just really bleak. And as sung by Judy in Meet Me in St. Louis, it’s particularly devastating.
“Smile, though your heart is aching / Smile, even though it’s breaking.” Has there ever been a more melancholy song about smiling? And Judy does it justice, naturally. She’s flawless here.
3. “The Man That Got Away”
Oof, A Star Is Born hits hard. This song in particular. I can’t hear Judy sing about romantic failings and regret without getting a little misty. The passion in her voice is incomparable.
4. “Happy Days Are Here Again”/”Get Happy”
Why are songs about happiness always the most depressing? There’s also an aspect of passing the torch here. It’s OK, though: they play it off as a bit. And we can take comfort in the career Barbra has gone on to have.
5. “You Made Me Love You”/”The Trolley Song”
It’s sad in the way that all late-stage Judy Garland performances are. You know that she doesn’t have that much time left — and although she still sounds great, she’s lacking the youthful exuberance that made her a star.
6. “Moon River”
So delicate, she almost seems fragile here. The song lends itself to that kind of performance — it has never sounded better.
7. “By Myself”
She doesn’t need ANYONE. (But she did. Oh, how she did.) The hardest lyric to hear? “All of those dark days are gone.” IF ONLY.
8. “I’ll Plant My Own Tree”
It’s a stupid number, yes. To understand why this is so painful, you need to appreciate the context: Judy was hired and then fired from Valley of the Dolls, too much of a mess to make it through the film. Just imagine what could have been.
9. “Over the Rainbow”
Her signature song many, many years after she sang it in The Wizard of Oz. One of the most gutwrenching renditions of the classic ballad. Now if you’ll excuse me, I have something in my eye…
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