It occurred to me, as I was posting my recent compilation of fierce songs to make you feel empowered after a break-up, that there are a few steps one must follow before getting to that place where you can say “I’m over it.”  The biggest?  A good cathartic cry.  And make no mistake about it; good music is just as capable at letting you wallow in the misery and pain, as it is at leading you to the other side.

After compiling this list, I realized that it could neatly be split in two; with half the songs falling into the categories of Jazz Standards and/or Stage Songs (i.e. Theater/Broadway/Whathaveyou), and the other half as being Contemporary (i.e. Rock/Punk/New Wave/Pop).  So that’s how I’ve done it.  Here, then, are the six songs comprising the Stage and Standards; songs that while not guaranteed to make you sob, are a damned good way to get you there.

5.  “I Think It’s Going to Rain Today” as sung by Angela McCluskey

This soaring orchestral single from Randy Newman’s eponymous debut album was described by the 20-time Oscar nominee* as “too maudlin” – but that’s exactly why this song works.  When delivered by Scottish songbird Angela McCluskey, the already weepy track will hit you right in the gut, leaving you feeling like all of the oxygen’s been sucked outta the room.

4.  “I (Who Have Nothing)” as sung by Dame Shirley Bassey

Shirley Bassey’s never met a melodramatic song that she wasn’t willing to belt-out; and “I (Who Have Nothing)” lets Dame Shirley sing as the woman scorned, watching her former lover and his new flame, inside restaurants. while she’s standing outside (in the rain, I assume), her “nose pressed up against the window pane…” (Though some fifty years later, it sure sounds an awful lot like stalking, to me.)

3.  “What’ll I Do” as sung by Judy Garland

Like Judy, “What’ll I Do?” (or as she referred to it, “Irving’s Song”) –  a 1923 Berlin ballad about getting over a recently-ended romance – is short, powerful, and packs a wallop.  

2.  "Send in the Clowns" as sung by Glynis Johns

While Judy Collins, Barbra Streisand, Sarah Vaughn, and Dames Elizabeth Taylor, Angela Lansbury, and Judi Dench have all sung gorgeous renditions of this Stephen Sondheim song from A Little Night Music; he wrote it for the great Glynis Johns, who originated the role of Desirée on Broadway.  A decade after singing “Sister Suffragette” in Mary Poppins, Johns would win a Tony Award for this gut-wrenching song that looks back with anger and regret on a mistimed life, with a seething intensity and more than a few tears.  And PS - the clowns are a metaphor.

1.  “I Dreamed a Dream” as sung by Patti LuPone

A truly theatrical lament, if ever there was one, either Les Misérable’s showstopper will have you reaching for your hankie by the time La LuPone sings “I had a dream my life would be so different from this hell I’m living.  So different now from what it seemed, now life has killed the dream I dreamed;” or you’re made of stone, and this article wasn’t meant for you, anyhow.

Sad Songs to Make You Cry

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[Editor’s Notes: Randy Newman has received twenty Academy Award nominations in the categories of “Best Original Score” and “Best Original Song” – winning the latter twice.]