25. “The Other Woman” (Ultraviolence, 2014)
First recorded by Sarah Vaughan, but made iconic by Nina Simone, both singers delivered “The Other Woman” with a certain distance. They sang as an impartial observer, or perhaps the wife, telling a sad morality play of a beautiful, loveless mistress. But Lana steps into the other woman’s shoes, embracing the beauty of the melody, the lushness of her lounge jazz arrangement. There’s zero separation between herself and the character she’s playing. Her voice quivers as she sings the closing lines -- “And as the years go by/ The other woman will spend her life aloooone” -- as if they’re the last notes she’ll ever sing.
This is the same downtrodden figure of “Ride,” “Ultraviolence,” “Shades of Cool,” who devotes herself to older men who’ll never really love her back. She’s so trapped by two ideals, young and beautiful, that there’s nothing else to her. On Ultraviolence, love is the ultimate drug, true believers are addicts, and Lana Del Rey is their prophet. “The Other Woman” isn’t just the final track on the album; it essentially exorcises Lana’s mistress character for good. She’d never sing about herself in the same way again.
24. “Yayo” (Paradise, 2012)
On Paradise, “Yayo” feels distant, drenched in reverb, as Lana warbles over piano like a lounge singer. But the original acoustic guitar-led version, the most significant track on 2010’s Lana Del Ray a.k.a. Lizzy Grant, is so intimate that it’s almost too sad to listen to. “Yayo” paints a stark portrait of a toxic submissive relationship: “I need you like a baby when I hold you/ Like a druggie, like I told you.” Her situation feels completely hopeless, but she persists with the charade: “Let me put on a show for you, daddy...” As the song ends, it feels like a beautiful death rattle. In either version, “Yayo” could be the most tragic song Lana’s ever written.
23. “Summertime Sadness” (Born to Die, 2012)
“Summertime Sadness” isn’t the most grand or moving song on Born to Die, but it is the most accessible. Lana’s lyrics are fueled by desire, but unlike many of her early songs, there’s no literal sense of tragedy: “Got my bad baby by my heavenly side/ I know if I go, I'll die happy tonight!” The phrase “summertime sadness” is seasonal -- it suggests a fever, a temporary affliction, a young love that knows it’s fleeting. Glamorous, romantic, but not overwhelmingly sad, the music video was a perfect realization of early Instagram culture -- think girls in flower crowns at music festivals, shot through nostalgic, analog-style camera filters.
Initially Born to Die’s fourth single, it wasn’t until 2013 that the Cedric Gervais remix made Lana the unlikeliest of mainstream pop stars. His version is hardly subtle, though it’s not as hammer-blunt as much of pop or EDM at the time. Even in a different sonic landscape, over electro-house synths and 4/4 kick drums, Lana’s distinct vocals don’t lose their personality. Though Gervais’ version was a bigger crossover hit at the time, it ultimately feels like it exists in an alternate universe -- Lana hadn’t heard the remix until it was on the radio, and has never shown any affection for it in interviews. The original remains the definitive version. It’s far more representative of Lana’s musical sensibilities, and in one of the first signs of her reach within popular culture, even inspired a Bangerz-era Miley Cyrus cover.