A Vintage Heartbreak Playlist

Sometimes, you just need a cathartic, mascara-streaming-down-your-face, ugly cry. And sometimes, that moment comes on Valentine’s Day, which one of my friends refers to as S.A.D. (Singles Awareness Day).

Whether it is a love that does not know you exist, a love who does know but does not care, or a love that once was but now can never be (translation: you were dumped), may these ten tunes about heartbreak, loneliness, and revenge cleanse your soul and start you on the path to healing.

And may next Valentine’s Day find you singing L.O.V.E.! xxoo

 

A quick note: I have chosen some of my favorite versions of these songs, but they are classics and have been done brilliantly by many different singers over the years.

1. “One For My Baby” – Frank Sinatra

Fred Astaire introduced this Harold Arlen/Johnny Mercer song in the 1943 film The Sky’s The Limit, but it is Frank’s version that most people think of when they hear the title.  Can’t you just picture him in some dingy little joint, tie askew, hat tilted to the side, stubble on his chin, clinking glasses with the bartender for the ninth time that night as he pours his heart out? I hear this song and want to be held as I reach for some whiskey to drink along with him.

Shameless Plug: I am hosting a new love songs show on www.MartiniInTheMorning.com called One For My Baby! It premieres on 2/14 just after 6p PST, and then moves to its regular night and time of Sundays 6-9p PST.

2. “I Wanna Be Around” – Tony Bennett

When you have been dumped, this would be the song to play down the phone as you call your ex at 3 a.m. to let them know that you wanna be around when they get their heart stomped into a million pieces. The best revenge really is looking fabulous and having a hit song, isn’t it? Johnny Mercer received the idea for the song and the opening line in the mail from a grandmother/housewife/beautician (depending on who you ask) who was inspired by Sinatra leaving his wife for Ava Gardner, and then Ava leaving Frank.

3. “In The Wee Small Hours” – Carly Simon

To paraphrase Ernest Hemingway, it is a lot easier to be hard-boiled about things in the daylight. But in the wee small hours of the morning it is a different story, as you long for the one you love while clutching the phone to your chest, willing it to ring (or even just buzz with a text).  Is there a happy reunion? People have wondered about that since Sinatra sang the song in 1955; the lyrics don’t give us any clues, and we are left with the loneliest early morning mood of all time, made especially poignant by the emotion in Carly’s voice.

 4. “You Don’t Know Me” – Ray Charles
 If you have ever felt invisible to your crush, this song is for you, as the woman Ray is crooning about is completely oblivious to the fact that he is smitten with her. He has an encounter with her and her man where Ray takes her hand for a moment, heart just about beating out of his chest, and thinks, I dream of you at night and long to kiss your lips. And she is perhaps thinking something like, this guy is staring at me a little too long and squeezing my hand a little too hard. So she walks away with her guy as Ray watches with an aching heart, the chorus in his head singing, “You don’t love me, you don’t know me.”

 5. “These Foolish Things” – Michael Buble
If you have ever lost a love, you know how the scent of their cologne or the opening notes of your song can instantly take you back to the time you were together.  In these heartbreaking lyrics, it is everything from a cigarette that bears a lipstick’s traces to a fairground’s painted swings that reminds Mr. Buble of what he has lost. There is a line that says, “Oh, how the ghost of you clings,” and while I do think this song is about a woman who simply left and moved on to someone new, when I really need a good cry I pretend that “ghost” is meant literally and that there is no chance for an earthly reunion. Unless perhaps Whoopi Goldberg shows up.

 6. “Don’t Get Around Much Anymore” – Natalie Cole

Don’t feel bad about staying home alone on Valentine’s Day, or even every weekend. Natalie missed the Saturday Dance, even though she tried to go and got as far as the door—it was the thought of everyone asking about her ex that (I’m guessing) had her making a beeline for her couch with some ice cream and a few episodes of Downtown Abbey. I have heard that it can take up to two years for every one year you were together to completely get over a breakup, so don’t be surprised if you skip quite a few Saturday Dances as you try not to stir up old memories.

 7. “But Not For Me” – Elton John

This song is such a perfect example of the genius that was (and continues to be, because their songs are timeless) The Gershwins, with music by George and lyrics by Ira. “But Not For Me” was introduced by the lovely Ginger Rogers (who was married and divorced five times, so she knew a little something about heartbreak) in the 1930 musical Girl Crazy. If you have been feeling like love songs were meant for other people, lucky stars are only lucky for other people, and every other person you see is tying the knot (but there is no knot for you), this is for you. And Elton, who made us all cry in the 80s with some of his fashion choices and “I Guess That’s Why They Call It The Blues,” has such a wistful tone that you want love to find a way and all of his dreams to come true.

 8. “Stormy Weather” – Lena Horne

The lyrics of this song remind me of living in the Pacific Northwest in the month of February; it has been gray and drizzly for months at that point, and will continue to be gray and drizzly for a few more months, and you are weary (so weary!) from the gloom and the pitter, patter, and spatter of raindrops. When you feel that you can’t go on, because everything you had is gone, Lena’s gorgeous song will add a little company to your misery and perhaps give your heavy heart a lift. And if you actually do live in the Northwest, you can look forward to some sunny and bright days in August.

 9. “After You’ve Gone” – Bobby Darin

First recorded in 1918 by Marion Harris, “After You’ve Gone” has stood the test of time and been recorded by about a bazillion other singers because the someday-you’ll-regret-leaving-me message never, ever gets old. And many times is true, as the dumper didn’t know what they had ‘til they dumped it. But until that day when your ex returns to you in tears, disheveled from nights of weeping over what they threw away and begging for a second chance, which you may or may not give them, gather strength from this song and the knowledge that you were the best thing that ever happened to them.

 10. “Body And Soul” – Tony Bennett and Amy Winehouse

“Body And Soul” is the most recorded jazz standard to date, boasting Louis Armstrong as the first jazz musician to record it. This version with Tony and Amy (from his Duets II cd) is especially poignant, as it was the final recording Amy made before her death in 2011. The lyrics speak of being sad, lonely, and full of sighs while offering yourself up on a platter to someone who is turning you down. Although the narrator/singer’s life is a wreck, there is hope that one day they will get a chance to surrender themselves, body and soul, to the oblivious one. And then perhaps dump them.