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  • Writer's pictureSilvana Smith

Vintage-y Jazz Music to Listen to Wine Drunk and Heartbroken

Updated: Mar 6, 2021

By Silvana Smith


Since most of the world has been snowed in or just stuck at home because of the (*cough*) panorama, I thought I’d offer some music recommendations for the genre that goes perfectly with a warm cup of tea (or some mulled wine *wink*) and your favorite weighted blanket whilst you look forlornly out your frosted window. In the shadow of Valentine’s Day and the gloomy clouds of winter, unless you’re one of the lucky coupled ones, it’s easy to feel a little down-hearted and in need of a good wallow during this cold winter month.


Whether it was your first Valentine’s Day since your pandemic break-up, the lack of sun’s really getting to you, or you’re just a little sad about that Tinder match you ghosted, it’s time to relish in your heartbreak, play up the drama, and put on some sad vintage-y jazz music. Even if your personal life is as non-existent as your faith in the American government, now is the time to pretend your husband’s lost at war, your beau abandoned you at the sock hop, or you’re afraid of getting drafted; any excuse to put on a little Ella, pour some wine, and make these long, dark nights as aesthetic as possible.


Besides the historical context of the immense loneliness of 2021, I was also inspired by some TV shows I’ve been watching recently that take place during the days of popular jazz music. From Mad Men (AMC) and The Crown (Netflix Seasons 1 & 2) to the overlooked cult classic, The Hour (BBC), to say these were some of the most aesthetically pleasing shows I've ever seen would be an understatement. The coiffed hair, tragic love stories, the Cold War, vintage clothes—they make these depressing, problematic worlds of the past look so beautiful. So, if the present-day gloom is making you want to escape to the much more classy and sophisticated melancholy of the past, here are some jazzy melodies to take you away. This playlist provides a healthy amount of wartime classics with a dash of select modern pieces, and a hint of some sexy French depression tracks.


"Angel Eyes" - Ella Fitzgerald (1960)


“So drink up all you people

Order anything you see

Have fun you happy people

The laughs and the jokes on met”


This song’s inclusion was inspired by the scene in The Crown where Princess Margaret, played by Vanessa Kirby, breaks down over her love for Captain Townsend, whose marriage proposal was denied by the Queen. Lost without the man she wanted, she turns to alcohol and jazz to soothe her emotions—an icon; my inspiration. Although I’ve never been through something like that, I do channel that heartbroken energy whenever my Trader Joe’s cashier doesn’t flirt with me.


"Body and Soul" - Billie Holiday (1957)


“What lies before me

A future that's stormy

A winter that's gray and cold

Unless there's magic the end will be tragic”


None of us truly knows what lies before us, especially underneath the haze of an unending national disaster that hit us the hardest this past winter. What’s worse is to feel completely ready to commit yourself to someone—body and soul—and have them feel as uncertain about you as our country’s future.


"I Can’t Get Started" - Ella Fitzgerald (1955)


“Dream, both day and night of you

And what good does it do?”


This is a song from a woman who has lived an adventurous and full life, but the one thing she can’t seem to do is sort out her love life. Although I don’t know anyone as accomplished as the woman in this song, many can resonate with the feeling of romantic false starts. And during a time of Zoom calls and lockdowns, sometimes dreams are all we have.


"I’ll Be Seeing You" - Billie Holiday (1944)


The perfect ballad for anyone who hasn’t seen their loved ones in almost a year. “I’ll be looking at the moon, but I’ll be seeing you.” Whether you’ve been separated for far too long or lost someone for good, the song ruminates in the space in your heart where they will reside forever.


"Fools Rush In" - Frank Sinatra (1960)


“Fools rush in, where wise men never go

But wise men never fall in love”


If you’ve ever felt stupid in love, take comfort in the fact that you’re not alone. Drink up.


"Misty" - Johnny Mathis (1959)


“You can say that you're leading me on

But it's just what I want you to do

Don't you notice how hopelessly I'm lost?

That's why I'm following you”


You might recognize this song from Silver Linings Playbook, but if not, it’s still a tender song of longing well worth the listen.


"The Hour" - Daniel Giorgetti (2011)


The theme song for the cancelled-too-soon BBC series The Hour is the perfect 50’s jazzy intro. The show is set during 1956 about a newsroom investigating communist spies, a tone that is definitely reflected in the ‘ticking’ percussion and eerie saxophone. It’s a show that also features a drunk and forlorn Vanessa Kirby playing a young woman unable to marry the man she loves. 10/10 would highly recommend this Emmy-winning miniseries.


"Solitude" - Billie Holiday (1952)


“In my solitude

You haunt me

With dreadful ease

Of days gone by”


No one is allowed to come for me about how much Billie Holiday is on this list. It’s not my fault her music is fantastic and encapsulates so many of the emotions we’re feeling during this panasonic. With “Solitude,” this song hits the nail on the head with the feelings of isolation we’ve all become accustomed to. The lines, “I sit in my chair/ And filled with despair/ There's no one could be so sad/ With gloom everywhere/ I sit and I stare/ I know that I'll soon go mad” were actually written about how I spent my Saturday night last week. True story.


"Le Moulin" - Yann Tiersen (2001)


From the soundtrack of the French modern classic, Amelie, is a melancholic track from composer Yann Tiersen. With an accordion and piano-driven song, there is no culture that makes depression as fashionable as the French. Please also check out the full soundtrack from the iconic film. Although it’s filled with much happier tunes as well, I could honestly listen to the album straight through on repeat.


"Impossible Year" - Panic! At the Disco (2016)


“The scars souvenir

That tattoo, your last bruise

This impossible year”


Although not actually a song from the past, the jazzy-Frank-Sinatra vibes are potent. The 2016 lyrics still resonate as the past year has felt utterly impossible to get through. Despite the scars of 2020 that we all still bear, we carry on. But just for tonight, don’t keep it all inside. Don’t be afraid to feel the gravity of our country’s catastrophe, if only for the drama.


"You Only Live Twice" - Nancy Sinatra (1966)


“You only live twice

Or so it seems

One life for yourself

And one for your dreams”


This haunting track from Frank Sinatra’s daughter was featured in the Season 5 finale of Mad Men and was actually the theme song of the 1967 James Bond film by the same name. A lot of us have been faced with our own mortality this year. If the life you are currently living isn’t what you thought it would be, take comfort in the lives you live inside your head.


"Days of Wine and Roses" - Henry Mancini (1962)


This serves as the theme song for a 1962 movie of the same name about lovers dealing self-destructive behaviors. The title comes from a poem by Ernest Dowson that’s recited in the film: "They are not long, the days of wine and roses: Out of a misty dream, our path emerges for a while, then closes, within a dream."


"I'd Rather Go Blind" - Etta James (1968)


This infamous blues song and her soulful vocal delivery make this track a 1960s classic, much like the great Etta James herself. Etta James was a famous Motown Singer that defined much of the musical era. Her life story also inspired parts of the movies DreamGirls and Cadillac Records, specifically the roles played by Jennifer Hudson and Beyonce. You can find modern renditions of this song by both Beyonce and Dua Lipa on Youtube.


"Vienna" - Billy Joel (1977)


“You can’t be everything you want to be before your time”


Another non-vintage jazz number (unless you’re proper Gen Z and the ‘80s are vintage for you), but the sentiment and sad piano melodies were too good to leave off this list. Here’s to hoping a better future still waits for us. Although there may not be a modern-day equivalent of taking your phone off the hook, it’s important to remember that it’s okay to take a few days off, log out of socials, and step away from the world. I promise the chaos will still be there when you get back.


"Gloomy Sunday" - Billie Holiday (1941)


Sunday is gloomy, my hours are slumberless

Dearest, the shadows, I live with are numberless”


The first part of 2021 definitely felt like a prolonged feeling of the ‘Sunday scaries.’ With the end still far off, many of us have been hitting the pandemic wall. The mundanity of another Monday working from the couch can feel super defeating. Although the subject of this Hungarian song is a lot more somber, Holiday’s rendition captures the intense feelings of loss and despair that haunt this modern era.


"Georgia on my Mind" - Ray Charles (1960)


“Oh Georgia, no peace I find

Just an old sweet song”


During a time that hasn’t seen a lot of peace, the good state of Georgia has definitely provided a bright spot this past year. This prolific and beautiful melody is included as an homage to the wonderful people and organizers that helped turn a voter suppressed state blue, but also as a sweet song about an enduring love. There’s actually a film about Ray Charles that features his history with this song, including getting banned from Georgia, and then later having this song become the official song of the state. This song has many popular covers from other jazz artists and modern-day musicians alike. (I recommend the Atlanta band, Microwave’s version for any emo kids out there)



Tldr; Tired of the current historical context of today? Let’s travel back in time to a world with much of the same terrible problems but with a cute vintage aesthetic. Listen along, and spend the last few weeks of winter in a jazz-filled, morose haze. (Actual heartbreak optional—we’re only in it for the aesthetic y’all) Don’t be afraid to romance yourself, and romanticize your own life. What the hell else are we to do in times like these? So, take your 2020 trauma and make it vintage.

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