10 Saddest Lana Del Rey Songs



Tumblr post again! I’m just throwing these on here to share them about and get some use out of my WordPress. These are the saddest Lana Del Rey songs – in my opinion.

10. Last Girl On Earth

Last Girl On Earth is one of my favourite songs by Lana Del Rey, a song about how “millions can hold” her but she’s feeling lonely: she can have anything she wants but she is the last girl. The way the song conveys the theme of loneliness, at least to me and my perception of it, is how the song sounds quite unique to Lana and I can’t think of any other song she has done like it (I’m sure there are examples but to me there isn’t), which makes it stick out to being a league of it’s own – a lonely song. The girl who has everything but having no one is a sad theme in itself. To be honest, this realistically isn’t one of her saddest ever songs, especially when some of the tracks in the honourable mentions* have themes of loss and betrayal that come across as more emotive and hard-hitting than a song that mostly lists all the pretty things Lana has, but to me it stirs emotion and I feel like the way she sings – a plain voice which never really changes and the careless way she speaks of lovely things as it all means nothing to her – make it a special yet low-spirited song.

9. TV In Black And White

This unreleased tune is a song dedicated to a man in prison, who Lana still loves and misses. There’s several reasons why this song makes me cry pretty much every time I hear it: Lana’s unfaltering dedication to her love, the way she bravely reminds him of the good times and how much he means to her is the first. Secondly, he loves her just as much, and “[holds] his pillow tight” at night time, clearly hating where he is and wanting to be with Lana. This relationship, torn apart, makes for a devastating love story. Thirdly, Lana clearly misses him a lot. The way she describes him as someone who made her see the world as something bright and beautiful, but now has no colour without him, tugs on my heartstrings too. There’s something about people who truly love each other yet cannot be together which is really upsetting, knowing that they are just within reach but a barrier remains between them. Finally, the way Lana sings. She puts such charming, sweet emotion into her voice and sounds genuinely hurt by the loss. The higher register she sings in gives the impression she is trying to be brave and positive, yet she cannot keep her voice steady and instead it goes higher – like when someone upset tries not to cry. The end of the second verse and the bridge – the way she sings even higher and stronger, with emotive conviction – underlines the sentiment. Again, comparatively not one of her saddest songs, yet to me, TV In Black And White is one that brings the tears each time, especially when her voice is so flawlessly sensitive.

8. Afraid

This is another song where Lana’s voice is what brings out the sorrow more than the lyrics or story, yet there is plenty of the latter within Afraid. Lana’s voice is once again high and despairing as it was in TV In Black And White, though this time more so. She sounds as if she has lost all strength and is on the way to hysteria, though the lyrics confirm her determination to get out of the relationship. When it comes to the plot of the song, Lana is yearning to leave her partner because she wants to move on and reach her dreams, yet at the same time she is feeling scared. Scared of what? Possibly scared of leaving the safety net of her relationship and current home but maybe something more. The song could be interpreted as her fear of actually leaving the man she sings about – afraid of his reaction, afraid of what he would do to her, suggesting an abusive or unhealthy relationship. She sings of feeling panic and fear, and how he has “nothing in [his] heart” and cannot change. The prospect that the song is about escaping some kind of abuse puts a dark twist on the song (it narrowly missed my post on Lana’s ten darkest songs for this reason but there’s not much to suggest this. Though Lana says she is “leaving now” and “done being afraid”, meaning she is breaking through of the cycle, the way she desperately sings of how he has frightened her – her voice sounding cleverly afraid and close to breaking point, as well as frantic in her need to get away – it is much sadder than it may come across as and her vocals never fail to break my heart.

7. Pretty When You Cry

There’s a theme on this list of vocals being the main thing that sways me when it comes to deciding how sad a song is: Pretty When You Cry is yet another one that shines. Lana uses unpolished, lo-fi vocals throughout this track, wavering over the melancholic guitar and matching it perfectly. Lana said she didn’t really touch up this song, making her voice sound authentic and letting the heartbreak come through very audibly. I think this is clever, and doesn’t appear on her overly-produced tracks frequently, so this song is special to me in that sense. The lyrics themselves paint a very glum picture: a woman who deeply loves a man who hurts her nor does he care. However much he hurts her, and “leaves and [he] leaves again”, she can’t bring herself to let him go. Though she brutally states that she “don’t mean shit to all [his] drugs”, she still holds on to the “memories” they have with one another. The entire song comes to a beautiful, climactic ending, with a very blue Lana quietly singing throughout the first half but the music – and her voice- crashing into almost a crescendo, her voice becoming angered and forceful and devastated before the powerful final chorus. The title, Pretty When You Cry, becomes sadder when you imagine she is trying to make excuses for the man again: rather than admit that he is a terrible man who doesn’t care for her, she seems desperate to believe he hurts her because she’s “pretty when [she cries].” The repeat of these lyrics, like a mantra to make it real to herself, could confirm this ‘theory’. This song, with it’s flow of changing emotions, imperfect style (which makes it perfect as the ‘live’ quality makes it feel more realistic) and inconsolable lyrics make this one of her saddest tracks yet.

6. Your Band Is All The Rage

This very May Jailer-esque song consisting of Lana and her guitar is a song I didn’t find until years after discovering her music, and I couldn’t help feeling so sad listening to this. It’s lovely acoustic song that’s full of heart and, of course, emotive singing. The way her voice strengthens and grows in want and mourning is so beautifully forlorn. The song is about how her boyfriend has more interest in his band rather than her, and though “[he] act[s] like everything’s alright” they both know the relationship won’t work. However, Lana’s dedication, much like in TV In Black And White, means that she’d let him go – even if he spends all his time with his band and doesn’t bother to call her. Yet, she’d still take him back all the same because she’s “gonna love [him] forever”. I highly recommend this song to anyone who hasn’t heard it, fan of Lana or not, because it’s so meaningful and raw that it’s impossible to not feel a hitch in the throat, or stare out the window dreaming of someone who you’ll love no matter what and no matter how much you mean to them. The finishing, mournful “I love you” sums up the song entirely – it’s a track based on love yet filled with unhappiness.

5. Pawn Shop Blues

Pawn Shop Blues is another song that is acoustic and stripped back, putting focus on the lyrics and Lana’s voice more than the beat. Once again (I’ve said this for every single song on the list and I’ll say it again) Lana cleverly uses her voice to push out the emotion, and the sound of Lizzy’s accented roots shines through on this track – it is, of course, from AKA Lizzy Grant – which gives it a much more raw, personal quality. This song is about letting go to better yourself – she lets go, physically, of earrings given to her by someone meaningful, resulting in her “almost [crying] as she sold them”, yet she is also trying to let go of this person too rather than merely the items she has received. Yet, though it’s about letting go and breaking up a relationship – or perhaps losing ties with her old life, her old home, her family – she is doing it for herself, to better herself. The most important part of the song can be considered a life lesson:

“In the name of higher consciousness
I let the best man I knew go
‘Cause it’s nice to love and be loved
But it’s better to know all you can know”

She is sacrificing her relationship and her love to move on and educate herself in the world – love is great to experience but she’d rather focus on herself and her knowledge. This sacrifice, and this letting go – for a good cause – make this song so upsetting. Though she is doing the right thing for herself, she is struggling to break those ties, and may not always be one hundred percent happy with that decision because she’ll always know what she’s left behind – and it’s a situation I would hate to be in, as I know how hard it is to make the right decisions and think of yourself.

4. Is This Happiness?

I discussed this song already in my 10 Darkest Lana Songs post so I won’t go too much into it again, but the soft throb of the piano and Lana’s gentle vocals invoke so much heartbreak. She sings of a difficult relationship, a “hard man to love”, and questions over and over “is this happiness?” Is the relationship right for her? The whole song is gorgeous and doleful, and naturally Lana pulls it off wondrously whilst leaving us all crying messes in her wake.

3. The Blackest Day

This song might just be number one for me – I have wept over this steady-paced track that sombrely shifts in tone and the five stages of grief very smartly many times. I feel this song needs much more attention as its flawlessness at capturing the feelings of someone who is mourning their relationship – or the actual partner – is difficult to imitate. The desperation of the choruses, the way the song very slowly builds to an almost panicked and feverish bridge (she sounds like she’s struggling to breathe in this part) – all of it hits hard, along with the breaking of the fourth wall in the exasperated outro (”it’s not one of those phases I’m going through, or just a song”). Her wordless vocalisations throughout the choruses, almost like wails of torment (though beautifully done) layer these emotions and I adore every inch of this song. To top it all off, the inclusion of Billie Holliday, one of Lana’s inspirations and an incredible blues singer, is a special touch that pushes even more of Lana into the song and truly makes you believe that it’s not “just a song”.

2. Blue Jeans

The first song I heard of Lana Del Rey’s that made me weep: Blue Jeans is one of her classics and one of her best. Everything, from the introduction of violins that immediately dips into the dark plucking of a guitar, the faithfulness of her love, the plot of the song, is stunning and woebegone. It’s easy to understand what happened: her partner got “caught up in the game” and started chasing money rather than sticking by her side, sort of like in Your Band Is All The Rage in a vague way, leaving her behind and eventually (most likely) getting arrested or paying gravely for his dirty work. No matter what though, Lana stoically would “wait a million years”. All of this makes this masterpiece a deliciously sad song, and the part that hits me the most is this:

“But when you walked out that door, a piece of me died
I told you I wanted more-but that not what I had in mind
I just want it like before
We were dancin’ all night
Then they took you away- stole you out of my life”

Her voice shifts to something more than weaving a pouting tale of woe, instead breaking into the pleas she used before to try and make him stay. One line in particular – “I told you I wanted more, but that’s not what I had in mind” – shows how her lost love was so focused on the money that he didn’t consider who request for more to being simply together, spending time with one another and maybe settling down. Instead he gauged it as a plea for more money, more wealth: what he was chasing, not her. The doomed love story falls very high on this list, and I often toy with it being number one. However, there’s one other song that guarantees a cry every single time and could be – maybe – even more devastating than Blue Jeans. This song is not Lana’s, but her cover of The Other Woman.

1. The Other Woman

Yes, it’s not Lana’s song – I’m sure some people would disagree that it should even make this list as it was originally sung by Nina Simone. However, this is my personal list and opinion, not to mention I can’t settle on an official list of what her saddest songs are: there’s too many that are incredible and it’s impossible to narrow it down. I’ve already gushed about The Other Woman before, so I’ll try not to go on about it too much. To put it in simple terms, it’s a brilliant cover and I think Lana has really captured the feelings of ‘the other woman’, straying from being the “bad bitch on the side” (Sad Girl) and showing that she will never be number one for the man she is seeing. It’s a more realistic portrayal, and that reality is hard hitting, especially when paired with her gorgeous singing and the transparency of her feelings. It’s hard enough being left behind, or losing someone to prison, yet knowing she will always be second best and only ‘the other woman’ – never the wife, never the mother of his children – causes an anguish so powerful we feel it ourselves. A controversial choice for number one? Perhaps. Yet it’s still undeniably one of the saddest songs she has sung of all time.


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