Behind the Scenes of Miley Cyrus’ ‘Endless Summer Vacation’

When Miley Cyrus’ “Flowers” debuted in January 2023, it topped the Billboard Hot 100 — and remained there for eight weeks. The album it introduced, Endless Summer Vacation (her eighth full-length and first on Columbia Records), went on to hit No. 3 on the Billboard 200. And a year later, the single and album both remain forces: At the upcoming Grammys, Cyrus (who has yet to win one) has six nominations, including song and record of the year nods for “Flowers” and an album of the year nod for Endless Summer Vacation.

Many of her closest album collaborators spoke to Billboard about how they came to take this creative trip with her — and why her Grammy recognition is long overdue.

All Aboard!

Mike WiLL Made-It, writer-producer: Since we’ve made so many hits over the years, Miley approached me and said she wanted me involved — she felt like this was going to be her best work yet. She has already explored so many different sounds, and she’s really on her songwriting. It’s always dope to work with her because she’s constantly pushing the envelope.

Michael Pollack, writer-producer: Miley and I had done a few writing sessions in 2021 with no real mention of an album. It wasn’t until we got back in the studio in January of 2022 that the momentum seemed to pick up and I started to notice Miley assembling Endless Summer Vacation.

Tyler Johnson, writer-producer: I think it was just part of being in the system after working on the Harry [Styles album Harry’s House]. And Miley’s team and our team — myself and Kid Harpoon’s teams — wanted to make it happen. We got together for a week at NightBird Studios [in Los Angeles] and wrote the song “Wildcard” and started our relationship with Miley. Six months later, after she heard some music that we had been working on with Kevin Abstract, she came over to do a potential feature on one of the songs.

Kid Harpoon, writer-producer: I’ve always been a fan. I just fanboy when she’s singing. When we [reconnected], she had some songs she liked but she didn’t have a production direction on them. The big thing for her was, “I want to make an album I’m proud of.”

Tobias Jesso Jr., writer: I ran into [Columbia CEO] Ron Perry at Adele [One Night Only] at Griffith [Observatory in L.A.]. He was like, “Hey, I’d really like to get you involved in this Miley thing.” In this particular session, I knew why Ron wanted me there: He wanted me to write a song on the piano with Miley. As soon as all the writers were there — Mike WiLL Made-It, Bibi Bourelly and me and Miley — I was like, “Why don’t we go to the piano and just try some stuff?” I think within 30 minutes, “Thousand Miles” was written.

Greg Kurstin, writer-producer: Ron Perry and [Miley’s co-manager] Jonathan Daniel both reached out to me about Miley. We initially got together to write songs and “Jaded” came out of one of our sessions with [writer] Sarah Aarons. We spent a lot of time at my studio. Miley is great to work with because she has a clear vision of what she wants and she doesn’t stop until she gets it. She’s also a lot of fun.

Caitlyn Smith, writer: Since Miley cut our song “High” on her 2020 Plastic Hearts record, she and my co-writer, Jenn Decilveo, had been texting about the three of us getting together and writing a bit for her next record. It was a last-minute “Want to write this week?” in April of last year that led to a day in the studio.

Jenn Decilveo, writer: [Miley] sent me this idea, and then we got together with my friend BJ [Burton] and Caitlyn, and that was the start of “Island.” I think it was at Larrabee in the Valley [in L.A.] — 1-2-3 done. She’s such an incredible songwriter and had so much input melodically, lyrically, productionwise. She was involved in every aspect.

Maxx Morando, writer-producer: We were just hanging out, and I was working on stuff and she was working on stuff, and she heard the instrumental version of “Handstand” and was like, “Oh, I have an idea for the vocal.” I made [it] during COVID-19 — and I don’t even smoke that much weed, but I think I was really high when I made it.

Gregory “Aldae” Hein, writer: [Columbia Records head of A&R Rani Hancock] was a cheerleader for Miley to work with me. Ron Perry FaceTimed me and was like, “Hey, we’re going to bring you in with Miley. This is what we want from you.” I went in with her and it was just instant chemistry. The first day we ever worked [together], we wrote “Used To Be Young” in less than an hour.

Stopping To Smell The “Flowers”

Pollack: “Flowers” was written in January of 2022 during a week of sessions at Sunset Sound [in L.A.]. The song came together organically, being written in its entirety at the piano. Initially the idea was slower and sadder, but both Greg [Hein] and Miley had the vision to make the song positive and free-spirited. We demo’d the song on Rhodes [piano] and left thinking it was a ballad — or at least I did. Almost immediately after, I remember being told, “ ‘Flowers’ is going to be the first single and it’s going to be produced out as an uptempo.”

Hein: Miley randomly texted us almost a year later, like, “Hey, just so you guys know, you have my first single.” Then she invited me to the music video shoot and I saw the scene where she walks up in the gold dress and I was like, “Oh, this is going to be a thing.”

Johnson: Ron Perry was really leading the charge of making sure “Flowers” and “Used To Be Young” were right. Those songs were definitely the priority, especially “Flowers.” But while we were working on that, we were doing other records, and it was actually [album track] “Rose Colored Lenses” that helped us gel.

Kid Harpoon: “Rose Colored Lenses” isn’t necessarily anything single-y, but we just loved it. Those songs are the soul of the record. “Rose Colored” was always the one that felt like the touchstone, but making sure that “Flowers” did its job in relation to that was important.

Johnson: It’s important for artists like Miley to have a level of autobiographical texture to their songs. Then you mix that with something people can move to, that feels new and retro at the same time, and it’s a really powerful cocktail.

Hein: It all comes down to, “I can love me better than you can.” That’s the all-encompassing lyric to me. I was in a city just now called Siguatepeque in Honduras and I was driving to meet a priest for my wedding coming up and there was no music playing in this city but “Flowers.” That one’s reach is just crazy.

Vacation Scrapbook

Smith: Miley arrived at the studio wanting to write this idea called “Island.” She talked to us about how being in the spotlight since she was a kid has put her on a bit of an island from the rest of the world and how it’s beautiful but, at times, can be really lonely. I’m obsessed with the hook: “Am I stranded on an island or have I landed in paradise?”

Decilveo: I love that line, which is one she wrote, which I think sums it up. Being uber successful, uber everything — is it paradise, or are you stranded alone? Not being able to go out because you’re so famous and you can’t go to Trader Joe’s because people won’t let you walk down the aisles like a normal person.

Smith: Also, Miley’s mom came by for a bit that day, and she had told us about this “Smoke ’Em If Ya Got ’Em” hat that she had bought. Later that day, we thought it would be a great line to put in the song.

Jesso: I love [on “Thousand Miles”] how country she gets on “Pick up the phone and I call back home, but all I get is a dial tone. And instead of hangin’ up, I hang my head.” It was really cool to see Mike WiLL Made-It be part of that too, because it’s not something you imagine, but he was so into it.

Mike WiLL Made-It: Miley took the song and switched the direction. I was already married to what we made but she took it to Grammy collaboration level. She got Brandi [Carlile] on the song and that was the piece that was missing. That’s how we ended up with the banger “Thousand Miles” we hear today before every Delta flight.

Morando: For “Violet Chemistry,” [Miley] was like, “Do you think you could add some sauce into this song and spice it up?” [My friend Max Taylor-Sheppard and I] thought, “What if we did some Erykah Badu bridge with a stinky bassline and something crazy?” It happened in maybe 15 minutes. We like the idea of throwing a wrench in something — a tasteful wrench.

Kid Harpoon: They’re very similar, Miley and Harry [Styles]. They’re giant pop icons, but their process is like an indie kid that just wants to have fun and doesn’t really give a sh-t about all the pop stuff. They just want to make something creative, so for those kinds of brains, going in and trying to write a pop hit is going to completely destroy all their fun. Me and Tyler [engineered] an environment in the studio where you can just do whatever the f–k you want.

Jesso: Even if you had a day session with Miley, it wouldn’t feel like a day session because she gets real so quick. She has just been so exposed in her life that she’s like, “What have I got to lose?” That’s a very fertile place for creativity to live. You feel a jolt of this creative energy from her, almost at all times. It’s sporadic and it’s crazy and it’s wild — but it’s the best kind.

Destination: Grammys

Smith: She seems to have arrived at a place in her life and her career where she doesn’t want to chase but simply create from the heart. I remember her talking about how even though she was successful and had reached this place and level in her career, it still felt like a treadmill, and she still felt like she was always “chasing the carrot.” She seems to have entered a season of life where she has found some peace and clarity. I think it shows in this record.

Pollack: Over the years we’ve seen so many sides to Miley and her music. Endless Summer Vacation is a representation of what all those elements look like when they come together.

Morando: This has been a long time coming for her. Endless Summer Vacation is a fantastic album; on top of that you have her whole career and everything that she has done before. Now [she’s] at this pinnacle.

Hein: It’s her most mature body of work.

Mike WiLL Made-It: This is the year where she wins album of the year after all the growth and hard work. This album, she found and unlocked another sound, that poster-girl Miley sound that no one can replicate.

Jesso: [2013’s] Bangerz was robbed. The Grammys need prison for Bangerz not being nominated for album of the year. Aside from that, I think it’s time for her to get what’s due.

Kid Harpoon: I still love Bangerz. It’s a classic. The thing I’ve always felt with Miley is that everyone wants Miley to win. She represents that part of everyone who doesn’t give a f–k and just wants to enjoy their life. I think this is a culmination of years and years of just being an absolute boss. People think, “Oh, someone writes Miley’s songs,” or “someone tells her where to stand, someone does this, and the record label says this,” but it’s not like that, and it’s a narrative that I just don’t think is helpful. And someone like Taylor [Swift], she’s helped change that narrative. That’s why I’m proud of Miley, because the Grammys will mean more, in a way, [now]. [A Grammy win is] recognition by your creative peers that you created this, and she really did.

Johnson: Without the Grammy, people are [still] singing the song. People are living their lives to this music. That’s the point of it. Grammys are a reflection of that already achieved milestone. We’ve already won — this would just be a bonus.

This story will appear in the Jan. 27, 2024, issue of Billboard.