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Essentially: Billie Holiday

I'm going to start looking at some of my favorite artists and compiling my favorite 10 or so tracks and giving them a small write-up, maybe going a little into the development of them as an artist - how they sound during different times of their career, how the songs make me feel and all of that other bs. I am going to begin with some artists that may be widely known (widely known enough to have truly essential songs), but are not particularly lauded or paid attention to on the red music site. The song selections will mostly be my favorites, but there is some effort to include "important" tracks, or at least some stuff that is indicative of change throughout the career. Not sure yet how all of these will go, but this one is a loosely ranked list. I think in the future, I'll do a slightly more chronological approach. We'll see. Just hoping to share my love for some of these artists and turn some people on to some good tunes. Spotify link for a playlist will be provided. Today, let's go into some of my favorite Billie Holiday tracks. She is one of my all-time favorite artists. I love how she is able to operate on all styles of jazz & blues throughout her career - most of her biggest tunes are standards (though, most artists of the time only sung standards), but her execution very often makes the songs feel like "hers" while other artists come across as "their rendition of a standard". Her career started as more of a feature singer for composers (Gershwin, Teddy Wilson, etc.) as well as more whimsical (even child-like), humble, happy, and positive-love-centric arrangements and then turned to a much more lounge jazz/blues with harder-hitting subject matter, more macabre arrangements, and more smooth or legato tracks. Enjoy! https://open.spotify.com/playlist/5NnYyl9xb0fHNE7Eg3WKSX?si=a86d1324f09f4f55
1Billie Holiday
I'll Be Seeing You

This exemplifies what most know her for - smooth and unassuming (almost lounge-like), yet gorgeous, intimate, and emotional. It is a perfect synergy of mood, vocal timbre and performance, and song selection. This may be my favorite song ever, honestly. The melody is so perfect for her curious and heartfelt inflections. There is a desperate yearning and vulnerability within her performance that is only brought out through the refrains of this track. This is one of the earliest songs ever that I would describe as “undeniable”.
2Easy Living

I’m a bit smitten by this track - it will transport me to slow-dancing with my partner and bring up many fond memories. Though, I don’t think that it is just happenstance - this track has a very homely, lovely, even meek or modest feel. This era of very early Billie can be so innocent and enjoyable. The oboe (I think) lead that foreshadows the opening vocal melody is infectious and Billie’s youth and sentimentality is on display in the writing and performance - everyone wishes they had someone who feels what Billie conveys in this track.
3Strange Fruit

One of the more important and impactful tracks of the era. Musically, it is tense, dark, and genuinely macabre, yet smooth and very strangely inviting. Very rarely do songs of this sort go through the musical progressions of nearly the entire song before introducing the vocal. The arrangement sets the tone for Billie to paint a picture of death and despair. This aforementioned “invitation” is amplified Billie’s performance, which pairs with the subject matter in a way that is very rarely captured - she isn’t inviting you in for a gentle evening of enjoyment, but for the most dehumanizing suffering imaginable. The content of this track is oddly NOT political, it is merely descriptive - I guess that is the power of imagery. There doesn’t need to be any convincing, argumentation, or pleading, the ideas of injustice are presented without context for you to witness. Every chord, note, lyric, inflection, etc., within this song is impactful. Not for the faint of heart - learn to love everyone
4Summertime

The Gershwin classic is, in my humble opinion, best executed my Ms. Holiday. A very early entry into her Rolodex of standards (1936, I believe) which saw her straying from the carefree and hopeful tracks that make up her earliest works. The instrumental here is a bit grimy and even urban - reminding me of a late night city alley in the rain. It is a track from a musical/play, so it makes sense that it sounds like it could be a Cab Calloway or Fats Waller original - the muted horn and muffled drums are the dead giveaway. It is supposedly written for an opera - a lullaby from a black servant to the young white baby for whom she takes care of. This context makes sense of many of the lyrics and adds a bit of impact and synergy to the rest of the composition.
5Crazy He Calls Me

Back to the carefree stuff… this song is just so whimsical and lovely. The legato strings build a perfect bed for Billie to wax poetic about just how in love she is - willing and somehow able to undertake superhuman feats to instantiate her love for her man. The timbre and meandering nature of her performance places the listener in a humble home in the country to a woman who may as well just be freestyling her whimsical love in a spur of the moment soft-spoken love tune.
6I've Gotta Right to Sing the Blues

Who doesn’t like a little bit of self-wallowing?? This is a pretty standard jazz standard - but everything just fits perfectly. There are few great moments the syncopation of the “all I see. For. Me. Is. Mis. Er. Yyyyy” is fantastic and it’s not super common for standards of this sort where you would usually find a much less staccato instrumental for the vocalist to layer over. Very unassuming little classic here.
7I've Got My Love to Keep Me Warm

Snow imagery means this makes it onto every Christmas playlist I’ve ever made. A little bit of love, a little bit of heartbreak, a shiny upbeat piece of jazz and blues to veil make people bop their heads to your sorrow - it’s got it all.
8Solitude

The TikTok kids have been making this go viral - I’m okay with it. It is the most loungey piece of vocal music you can find. Broody saxophone, sustained and soft piano chords and arpeggios, and open ended upright bass fills all tie this thing up in a bow for Billie to sing straight into your heart. The one word title embodies the atmosphere of the track so well - Solitude.
9Riffin' the Scotch

Upbeat and infectious. The steady 1-2 of this song keep it pumping the whole way through. It is all around fun. Despite being very early in her discography, to me this feels much like the jump blues that would come about in the later years of Billie’s life (popularized by the likes of Wynonie Harris, Roy Brown, even Louis Jordan), though it definitely has the big swing band influence as well. It features Billie for only roughly 30 seconds, but a fun 30 seconds it is.
10Blue Moon

Everyone knows the song. Everyone of the era sang the song. Billie did it better. A more contemplative take on one of the most widely known standards of all time. It is the perfect rendition - placing the listener in a quaint jazz club late amongst candles and a relaxed atmosphere. Billie is untouchable, ya’ll.
11Honorable Mentions
Honorable Mentions

Let's Call a Heart a Heart
You Go To My Head
I'll Get By (As Long As I Have You)
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