By Miles Raymer
February 11, 2015 at 12:00 PM EST

Hailey Tuck was born in Austin in the early ’90s, but she’s got the soul of a Jazz Age libertine, hence the Louise Brooks haircut, her love of Edith Piaf, and her decision to drop everything and move to Paris to find her fortune. Apparently on the path to finding a career channeling the prewar jazz she loves, she also encountered a lot of heartbreak, so although she boasts a version of “My Funny Valentine” worthy of the holiday, she’s also made EW a playlist that can appeal to those of us with gothic tendencies and not-so-fuzzy feelings toward Feb. 14.

1. Blossom Dearie – “Now At Last”

I have to kick this goth playlist off with my all-time favorite softie-singer (and one of the most underrated pianists in jazz) Blossom Dearie. Of course the worst breakup of my life was with–you guessed it–a jazz pianist. He was older than me, successful, and wildly talented. He first introduced me to her, and when self-flagellating through our breakup, I would listen to this song (and even sent it in a few pathetic emails!) and think that at 22 (ha!) I’d never play with anyone as well, or love anyone as much, and that all I was good for was lying in bed covered in Doritos dust and mainlining Andre. Needless to say; my next boyfriend was a model…

2. Duke Ellington -“Lotus Blossom”

This song transports me right back Paris–the perfect setting for all my prime breakup years. I specifically chose this live, impromptu version of this song from And His Mother Called Him Bill, a memorial tribute album to my king of goth jazz, Billy Strayhorn, Duke’s best friend and writing partner. When the model I was dating, who also said I had uneven shoulders, finally dumped me, and when I couldn’t understand why the philanthropic businessman, who was twice my age, didn’t think I was the right person to save Africa with, I would put on headphones and listen to this album on repeat and remember that I had a tribe, and they had all lived and been star crossed right there in Paris.

3. Jamie Cullum – “Good Morning Heartache”

I first heard Jamie’s version of this when I was opening for him in Paris, and was shocked to find I loved it even more than my original favorite version by Billie Holiday. Jamie is like a firecracker on stage but his dreamy, dark take on it is exactly the sort of goth jazz I want to hear when wallowing in self pity after a breakup. Though he is such a sweet guy, I have a feeling he’s one of those pesky impossible-to-hate exes. 

4. Chet Baker – “Everything Happens to Me”

My favorite recording of this song, is actually by the writer himself, Matt Dennis, But that recording only exists in the shadows of YouTube. So my second favorite makes the list, not only by being one of my favorite songs that I sing on every show, but by virtue of the man who could have truly dumped me the hardest: Chet Baker. In many moments of jazz psychosis I have totally fantasized about going back in time, saving Chet Baker and spending the rest of our lives playing duets in a dilapidated Haussmannian apartment in Montmarte. However, the truth is, even if I could go back and live out this masochistic little fantasy, we both know that Chet would have probably spent two months with me, robbed me, and dumped me to move to Berlin.

5. Billie Holiday – “You’ve Changed” 

A lot of people bash Lady In Satin, because Billie’s voice had deteriorated so much, but I have always loved it. Billie’s voice was always brimming with grit and raw emotion. I hear a tired woman, using jazz as a conduit to reflect on her own repeated heartbreak, and self abuse of the last several decades, and that sort of rare honesty just slays me. We all need a release when we’re down, and can only hope we find it in lighter corners than Billie did. 

6. The Zombies – “The Way I Feel Inside”

Picking just one song from these guys felt like Sophie’s Choice, because when you watch the 1960’s video’s of girls screaming and fainting at Zombie’s concerts, that’s basically me every time I listen to the Zombies, which is a lot less cool these days, especially while driving. I also realize this isn’t technically “Jazz” but since I am the self-aggrandizing DJ of this playlist, I can do whatever I want – including my own Bossa nova cover of Tell Her No from my first EP. I chose this song, because being relatively short and mostly a capella it reminds me that often stating something simply and honestly, can be just as entrancing as a lot of flowery prose and production, which I worry about when writing songs. But judging from the naivité that I think most of us see in the hindsight of our relationships, maybe the truth in that is important.

7. Nina Simone – “The Other Woman”

Man this song does what Nina does best! She sings a song with such heart, and pain, and truth, that you feel like she’s right there with you, in front of a fireplace, sitting in an armchair in the dark with a glass of scotch in your hand, and at the end you throw your glass in the fireplace and whisper a strangled, “AMEN!” You do do that don’t you? Okay, maybe the arm chair is a bar stool, the glass of scotch is possibly corked white wine, and the “Amen” is directed towards a jukebox at dive bar full of felons, that maybe should be burned, but definitely does not include a fireplace. Regardless I think all of us have been here in the form of 3 a.m. internet stalking sessions.

8. Chris Connor – “Lilac Wine”

Chris Connor rocks, and it’s treason that she’s not a household name. Especially since that owes mostly to her being gay (and out!) since the 1950’s. Brave. This song is from my favorite album of hers, Chris Connor Sings the Ballads of the Sad Cafe. It helps me time travel to the summer of 2007, working in a tiny rare book store in Austin and reading a gem of a depressing short story “The Ballad Of The Sad Café,” a fantastic story set in the South, about betrayal, and longing, and all of those things us Southern belles and Russians so love to write about. How this relates to a breakup you ask? I met a guy while working at that shop who immediately struck me as the future Mr.Tuck–he was a rich, funny, writer, and Grandmaster of meeting my parents. What could ruin our pre-pre-nuptial bliss? Blowing me off for willowy Swedes who couch surfed with him.

9. Bob Dorough – “But For Now”

Remember School House Rock? “Three Is A Magic Number?” That’s this guy! I sang with him at his Austin show as one of his “Bobettes” as back up, and most excitedly got to sing a solo for “Figure 8,” originally sung by Blossom Dearie. At 89 years old (then) he was one of the best, most generous musicians I’d ever seen, blowing away a town chock full of musicians who couldn’t have held a candle to his passion and exuberance! and even stayed up and partied with us, drinking Guinness.  The moral of this story? Find what or who you love, and love it enough to make it special even after almost hundred years. 

10. Frank Sinatra – “Why Try To Change Me Now”

I’d like to end the playlist with one by one of favorite composers, Cy Coleman. You might know him from another one of Frank’s hits: “The Best Is Yet To Come.” I recorded this song with my ex during a break up (apropos) and that demo ended up being the one that got me a meeting with my current booking and management. So this Valentine’s Day, remember to cherish not only being wildly, madly in love, but also completely pathetic and heartbroken, because either can only lead to new and exciting things. And if not, there’s always adopting a cat or ten.