Tracks 3 and 4 from Meet Miley Cyrus (2007)

Tracks 5 and 6 from Breakout (2008)

Tracks 15 and 16 from Miley Cyrus & Her Dead Petz (2015)

It's funny to think now that Hannah Montana, the pop star alter ego that Miley Cyrus played from 2006 to 2011 on the Disney Channel sitcom, was a cottage industry unto itself for a while there, selling millions and millions of albums. But Cyrus began to differentiate between the music she made in character as "Hannah" and the music she was making as herself, "Miley," pretty quickly, in 2007, when Hannah Montana 2 was packaged as a double disc with her 'debut' Meet Miley Cyrus, and she performed both repertoires on her Best of Both Worlds Tour. 

Hannah Montana still has her own Spotify profile and her own discography page on Wikipedia, separate from Miley Cyrus. Looking back, it feels pretty silly, since there's very little musical or vocal difference between Hannah or Miley's music, if any, and it was easy to mix them together -- the first 12 tracks on this playlist are all of a piece, and you probably wouldn't be able to guess without looking which 4 songs are Hannah and which 8 are Miley. The Hannah Montana The Movie soundtrack album confuses things even more with songs credited to Hannah and songs credited to Miley. Of course, the Hannah songs ruled Radio Disney, but for the average pop fan, every song she's remembered for now is a Miley Cyrus song. 

Miley Cyrus made some vague gestures at becoming her own independent-minded edgy singer-songwriter on Breakout and Can't Be Tamed, but all of that felt very minor and quaint compared to the reinvention on Bangerz, her first album after finally closing the door on Hannah Montana. Many white pop starlets had made 'grown up' albums with sexual lyrics or hip-hop-inspired production before Miley Cyrus, but it felt like she was determined to really go further and go for more shock value, and it worked in a sense, because the album was an enormous hit. Personally, I hated "We Can't Stop" and most of the stuff she did in 2013, it all felt so forced. But revisiting that record now, I will admit that she and Mike Will Made It had some cool synth pop tracks like "Drive" and "Maybe You're Right" on there. 

After Bangerz, Cyrus pivoted hard again, and Miley Cyrus & Her Dead Petz is one of the weirdest, most uncommercial albums a pop superstar has ever made at the height of their fame. Many of the songs were written with the Flaming Lips, and Ariel Pink and Phantogram's Sarah Barthel also make appearances, but Cyrus also continued working with Bangerz collaborators like Mike Will and Big Sean, so it's just a bizarre mix of styles. I want to admire it, but at 92 minutes, the album is incredibly indulgent and at times unlistenable. As much as I loved Halsey and Trent Reznor mixing contemporary pop with '90s alternative rock on If I Can't Have Love, I Want Power, that's how much I hate what Miley Cyrus and Wayne Coyne made together. Still, I tried to pull a couple of the more tolerable songs from the album for this playlist. 

Since Bangerz and Dead Petz, Cyrus has sort of stopped flying between extremes and worked out a more toned-down pop/rock sound and image and made some of the best music of her career. She Is Coming was a heavily hyped EP that seemed like part of a major rollout, but then no album followed it, much like The Time Of Our Lives contained one of the biggest songs of her career ("Party in the U.S.A.") but then it never lead to a full album. I love the song "High" on Plastic Hearts, and co-writer Caitlyn Smith recorded an even better version for one of my favorite albums of 2023.