Lana Del Rey’s shadiest moments, along with her trademark sad girl aesthetic and effortless silvery vocals, have shaped her as one of the most iconic figures in pop music.

Since her 2012 debut, Del Rey has seamlessly blended genres, defied standard release schedules and collaborated with unexpected artists (see her upcoming Charlie’s Angels soundtrack single with Miley Cyrus and Ariana Grande). She’s taught us that we know nothing about her next move — like when she set up a witchy lair in the H of the Hollywood sign, or dropped a killer Sublime cover out of the blue that saved our collective summer.

What we have come to expect from the “Video Games” singer, however, is an endless amount of shade ready to be thrown whenever it’s called for. Some have had to learn the hard way that Lana Del Rey is not one to be messed with. She tells it like it is, and she’s ready to give you “the addy” and permission to “pull up anytime.”

Below, check out 20 of Lana Del Rey’s best shady moments.

Lana Del Rey's Shadiest Moments

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