It mostly comes down to her making everyone feel very, very old .
Terry Richardson / Via terrysdiary.com
When Jay Z's "Somewhere In America" came out in July, it was hard to tell exactly where he was coming from when, at the end of the track, he urged Miley Cyrus to keep twerking with a hearty laugh and an audible smirk. Was he scolding the young pop star, who has been called out many times over this year for appropriating black culture? Or was this his way of lightly endorsing her obvious enthusiasm for hip-hop? Naturally, he was asked about this several times over while promoting Magna Carta…Holy Grail. His most interesting explanation was in a Q&A with fans on Twitter, where he described Cyrus as "an old world's worst nightmare," i.e., "black neighbor, and the daughter not seeing color."
This didn't clarify whether or not Jay likes Miley, but it does show that he understands something that a lot of her critics do not. Cyrus' appropriation of hip-hop — specifically, trap music and "ratchet" style — is notable because she doesn't seem to notice that it's sort of weird for a Disney channel actress/tween pop idol/daughter of a country star to be twerking at the MTV Awards and rapping over Mike Will Made It beats. To her, and to many of her fans, this is a totally natural progression because hip-hop has become a default setting of pop culture.
What is it about Miley Cyrus that aggravates so many people, but also makes her the biggest pop star in America right now? The biggest reason is probably that she makes a lot of people feel very old.
Cyrus, who is about to turn 21 in November, is young enough that her frame of reference for pop music has always been dominated by hip-hop. She's also from a generational cohort that has grown up on social media and is conditioned to share culture in a performative way. Think of it like Tumblr's reblog function — where what you share with others represents how you want people to think of you, even if what you're sharing isn't necessarily who you are. This mentality disrupts a lot of the self-consciousness earlier generations have had about cultural borders. Miley — and many, many, many other artists and music fans around her age — aren't "not seeing color" as Jay Z says, but they're not seeing race as a boundary they can't cross, or something they can't freely integrate into their own identity. Miley isn't actively trying to be a cultural imperialist, and she has no statement to make other than "I really like this!"
This approach to art and culture isn't without its problems. Her enthusiastic appropriation of trap and ratchet isn't automatically racist, but it does come from a position of privilege, and it's not difficult to see it as exploitative or condescending. But you could say that about a wide range of white artists who have been influenced by black music over the past several decades. Miley's hip-hop makeover gets under people's skin mainly because she doesn't seem to have the slightest bit of interest in what makes it potentially insensitive or opportunistic on her part, though she seems very aware of the transgressive quality Jay Z touched on. She knows that it will freak out a lot of people — older people — if the precious little white girl goes black. It's good old-fashioned rebellion, and something many of her fans can relate to, or enjoy vicariously.
Miley also makes people feel old simply by being a pop star who up until very recently was just not on their radar, though she's been a major star among teens for years. Her notorious performance at the MTV Video Music Awards in August was shocking for a lot of reasons that have been discussed at length — Miley using black women as props, her grinding on Robin Thicke's crotch — but in a less obvious way, it was jarring because from the perspective of pretty much anyone over 25, she wasn't supposed to be the biggest star of the show. Miley stole the spotlight away from Lady Gaga, Katy Perry, and Kanye West, and made them all seem bland and overly self-referential. It was a sudden, unexpected changing of the guard: Now, whether you like it or not, Miley is the most provocative star in pop, and all the people you expected to be pushing the envelope seem old and boring. And even still, in the aftermath of the VMAs and the massive success of "We Can't Stop" and "Wrecking Ball," there's still a lot of denial of Miley being as popular as she is. It won't last much longer.