Carly Rae Jepsen Says Her New Project ‘The Loveliest Time’ Is Her Favorite — and Freest — Album Yet

After Carly Rae Jepsen released the album Emotion in 2015, her A&R asked to see the songs that had ended up on the cutting room floor. Jepsen wasn’t ready to let them go, but she also didn’t know if they would ever live to see the light of day.

A year later, she found an excuse to revisit them and released the EP Emotion: Side B. It birthed a new series both Jepsen and her fans love, one she refers to as her “B-sides.” After releasing Dedicated in 2019, Dedicated: Side B followed, this time as a proper companion album. Last year’s The Loneliest Time also has its own yin to its yang: The Loveliest Time, out July 28th.

“I was so nervous about the concept of putting out ‘B-sides, and then I did it, and it was so gratifying just to have extra material to play at concerts,” she tells Rolling Stone.

Jepsen and her collaborators put constraints on this particular album, wanting to finish it before a string of live dates later this summer (she’s playing with Boygenius and also headlining on her own.) While on an extensive world tour in support of The Loneliest Time, she hunkered down in hotel rooms and studios and tour buses to workshop the songs she felt best told the other side of the story: She wrote about the joy and elation of getting over a break-up and a too-reflective time in pandemic isolation, coming out on the other side to find new love and a new perception of herself.

Jepsen spoke with Rolling Stone about the two albums, the “B-sides” project overall, and why this is her favorite album she’s made so far.

Do you look at this as an extension of your “B-sides” series or is it something totally different?
I think that I look at it more as a complete set with The Loneliest Time. It’s definitely a companion project to it, but it is also a “B-sides” in every sense of the word — that it is songs created during an era, that I always had intended to put out. But I think as I was even selecting [tracks for] The Loneliest Time, it became clear to me that these weren’t just songs I cared any less about. These are songs that in their own right had a place on this album. I just couldn’t have a 30-song album. 

I think the tradition of doing a “B-sides” is something that I’ve really fallen in love with. Especially because I write so much and I kind of go and explore in lots of directions, it feels like a shame that so much is left on like the cutting room floor. This became an avenue for me to get to share more of what I make and that I love equally. “B-sides” has just become the title for a place where I let my freak flag fly. I get a little bit more experimental with things I feel like there are even less rules — not that I bind myself to rules, per se. But sometimes in the first offering, I’m a little bit more like, “Okay, there’s got to be a little bit of this and a little bit of that.” The “B-sides” are my playground.

Given Loneliest and Loveliest as the chosen titles, was there a distinct separation you noticed in writing each album? Or were those feelings of isolation and joy coalescing for you?
I didn’t want it to just be as simple as a dark and a light. We’re not as simple as that as humans. The Loveliest Time isn’t just sunshine and flowers and butterflies and “Everything’s okay now!” It’s more about stepping into the experience of being alive and coming out from that state of hibernation and then loneliness. A lot of important lessons, I think, are learned. We were all forced into this place with COVID to really look at ourselves and our life decisions. I definitely was. I was like, “Gosh, I live alone in a house with a cat. And I tour, but like, what is going on?” I felt like it was really a playful subject to look at loneliness. Even “Beach House” is a theme of that, like going on a dating app. You might be demoralized by that experience and trying to find the humor.

The Loveliest Time is a bit more about ownership of [yourself]. I’ve really discovered it. I know what’s good, and what’s bad, and what’s ugly, and everything. You’re taking those lessons, learning from it but going back into the wide, wide world and being ready to face it. 

There are so many flowers in a lot of my images because I like the idea of planting yourself in this clean dirt, and from this, a beautiful growth can happen. I want it to like feel like growth and sound like celebration. Those were the main concepts for me. 

It’s funny because a lot of the songs are about the wild feeling that you will do anything to make yourself feel alive. Opening with “Anything to Be With You,” it shows a “we will make it happen” feeling. It’s a little movie-esque in that way. But I want my life to feel as wild as that. And a lot of the songs were written from a place where I still hadn’t met anybody I was that excited about; it was this longing for that. It’s been a weird thing of life imitating art because I feel like I’ve written all these experiences that now in real life I’m getting to have and it’s odd to have it be written first and then kind of happen afterwards.

The power of manifestation…
Yes! I’m like “I’m going to use this for more travel on the next album.”

I know you’re a very prolific writer but was there a song or two created in the process that built the foundation of The Loveliest Time?
I really wanted “Psychedelic Switch” to make it onto this album because I think that is exactly the concept that we’re talking about of a light bulb turning on in your life. It’s also about the experience of really being present in the moment. It’s less like, “Now I found a partner and everything will be perfect.” It’s just really living in the moment of feeling stuff. I’m a big campaigner of that. “Psychedlic Switch” is almost like the the sister song to “The Loneliest Time.” Those are the heads of each project.

It was important to me that “Kollage” was on this album, even though it is a darker offering. It’s more melancholy and deals with realizing that when you hurt yourself, you’re hurting the people that love you. It’s about coming to that place of owning your shit. Part of self-love is self-acceptance of that stuff too. 

I think that “Kollage” was almost too heavy for me to be ready to share [on The Loneliest Time] on a personal level. I was more ready to be like ‘Okay, we’re gonna go here.”

If I were to summarize one of the greatest gifts that my fans have given back to me, it’s the feeling that anytime I think it’s too much or if it’s gonna go to a dark place and I feel like they’re expecting to me to be a little bit more escapism and happy music, it’s received with so much love. Like “Bends.” I was really frightened to share for that reason and but felt, if anything, like it’s a song I actually reserve in my set as a moment to reset the crowd. For me, it’s been such a learning experience. Who made these rules about how I couldn’t go to those places? Was that me or was that somebody else? I’ve broken them now. The dam is broken. It’s all coming up.

You introduced this new album to your fans with the song “Shy Boy.” It’s the perfect example of a facet of your songwriting I find to be the most underrated: your sense of humor. I loved that on the song “Beach House” from the last album as well. 
Well, it’s funny…I’ve learned from going to my therapist that I use humor anytime I have anxiety. She’s like, “You’re just cracking jokes again!” But I do feel like you just tapped onto a part of my personality. It’s funny that it comes out in the songwriting too. Like with “Beach House,” it’s obviously traumatizing to go on on a dating app, come back and be like, “It’s terrifying out there.” But you have to find the humor. I feel like what helped me get through those [bad dates] was calling my sister afterwards to be like, “Okay, he made muffins. Actually, I think his mom made muffins…” and you’re just dying laughing. How can I not want to put that into a campy song?

With “Shy Boy,” I brought this song on my shoulder through years of my life, like a little backpack I was carrying with some little hooks here and there. I wrote parts of the song before I had “Call Me Maybe,” actually. The part “It’s like this/Put you on my list/So come downtown” was a little thing I wrote when I was in Vancouver. I had met a guy that I wanted to have come to my show when I was playing pubs. This will happen with me through the years where I’ll have a little bit of a baby concept and it’ll follow me enough that if I’m in a session, and we come up dry that day, and I trust the people in the room, I might be like, “Hey, like, how do you feel about this concept? You want to rework that?” 

With “Shy Boy,” this happened many times throughout my life since then. And it would always change and I’ve always improved it, but it was never quite there. This was such a victory to get, and I had so many of my favorite people help put their genius into that: Nate Campany, Nate Cyphert, Kyle Shearer were on one session. Ethan Gruska helped me rework it. James Ford reproduced it and helped put the final touches on it. 

I listened to the final result when I was in London, and I had just had a session with James. We’d done some ad libs, and I remember dancing. I was so worried that with how much it had gone through that it would not feel effortless to listen to. But it feels easy. It feels simple. It feels like flirtation. The song is literally about one of my favorite pastimes, which is confidently being the one who can take charge in a situation. I think as I’ve gotten older, I’m more ready to be the first person to make the move. Like with my current boyfriend, he definitely blames me for us beginning. I love that feeling. There’s something that you kind of learn about yourself when you can kind of be the first person to put a move on.

Are there any other moments like that on the album, where bits of a song pre-date even The Loneliest Time sessions?
“Anything to Be With You” was an idea that had been chasing me in different forms as prior to this. I think like the hook started in a hotel room with Tavish Crowe, my guitarist and my keyboard player. It took on a lot of different forms before it landed where it did. And to me, that song is the most unique thing I’ve ever been a part of making. I’m really happy where it landed because it took on such a journey as well. 

I should probably state that my favorite process, and why I love “B-sides” so much is that it’s one thing to write a song during a period of your life and to put it out. It is another thing to write a song about a period of your life and put it away and then come back a year or more later, look at who you were back then, the decisions you made back then, why it got frozen in time, why it didn’t make it to that album and then go back in and workshop it. I didn’t just have these songs and go “Oh, ‘B-sides’ is due let’s put it out.’ I went back in. It’s almost harder than putting out a first album because you’re going in and trying to workshop and problem solve and rethink. Sometimes it’s easy because you’ve had that time and perspective and you’re like, “Oh, my God, the chorus was visibly over here. What were we doing?” And sometimes it’s like, “Oh, I know, there’s something here. I need help. Let’s just try to get some new fresh eyes on it.” 

I think any time that a song goes through stress tests and workshops, and you’re digging for that diamond, you know when to stop. You know when you’ve overworked it. It’s just a better process. It’s just to me how I think great music can be really improved upon. 

This is now the third time that I’ve done something like this, and I’m like, “Why isn’t all music made this way?” I almost want to like scream it from the top of the roof or like do like a TED Talk to other producers and writers about it. I love that I get to have some time away. I’m back with fresh eyes and really look at a project critically and then kind of get to some solutions. I would say each song has gone through that process to an extent. Songs that were really simple, really easy took almost no work from The Loneliest Time to now? I’m trying to think if there was one of those, and I think the answer is no. I think they all went through the washer and dryer before they were ready.

I’m sure it’s also helpful to go through the nerve-wracking process of seeing how fans and the public respond to a new album then getting to further expand on the joy of sharing it with them. How much does touring an album while working on the “B-sides” affect the final product?
You should join my TED Talk! It’s an idea that I feel like more people should hook into because that creates such interesting intel, You’re out there touring in real time while you’re creating this other side project. So I would be on the road in the UK and then I would go do a session and I would be in Australia and we’d like be finishing a session on the three days that I was home. A lot of this was done in between tours, in between a world tour where I was like Japan for a bed, I’m entering Canada, I’m here in the US, and you’re getting to kind of see in real time how people are reacting. And like I said, it was kind of mind-blowing to me to be able to play “Bends.” So that encouraged things like “Kollage.”

I had the luxury of having my bandmates who were very invested participants in everything weighing in over the time and on buses to be like, “Oh my God, you have to use this one.”

I think we can be a bit more bold and go for the gut. I was also very encouraged by my A&R and by my team. We would ask ourselves, “What are ‘B-sides’ for?” We decided it’s to grow and to experiment and to play and to let this be a place where it is a little bit more like a passion project than anything. 

It’s really fun to have that support. It’s so opposite of when I entered into this business around “Call Me Maybe.” The conversations I’d have with my label were very much like “What you did this last time, can you do that twice?” This was very much “Do whatever you haven’t done before.” “Okay, I would love to do that. Great meeting everyone, have a doughnut.”

Is there a song you didn’t expect to make this album but maybe after playing a show realized it might be fun to play live?
“After Last Night” was the last song to make the album. It sounds like a musical in space. I don’t know how else to describe it. Rostam Batmanglij and me had conversations where he was like, “I don’t think there’s any other artist who could put out this one. We should do it. Let’s enjoy the fact that it is a little bit over the top and that you kind of need to move your body when you listen to it.” 

I got encouraged to do that one when I was playing “Shooting Star” and you’re realizing that those sort of songs are almost like a video game song where it’s like you’re at this level, and then there’s not another chorus, there’s just like another little level that you go to. I think after so many years of doing the Swedish way of writing pop songs where it’s versus-previous chorus-bridge, it’s so fun. That’s been a place where I’ve really enjoyed sort of knowing the rules and breaking them.

With the idea of breaking the rules, you saw a little spoken monologue go viral from your song “The Loneliest Time.” How does a moment like that encourage you to keep experimenting and trying new things?
If I’m being really honest, just comes more from age. I’m giving myself more permission to do that at this point in my career. I think maybe if I was like, 19, and just starting, I’d be like, “Oh, God,” but I feel like I can play now. I feel like I’m at an age like where it is essential to play, actually. I think about my favorite sort of longtime legend artists that I look up to, like Queen and Elton John, and they’re not playing by anybody’s rules. 

And I think as a songwriter, I’m constantly just trying to evolve and grow and get better. One of the joys of that is, I think, entering into a phase of just trying things and experimenting and growing and not being afraid to sort of question those, those rules that someone put in place.

To me, I’m more excited about this project than I’ve been about anything that I’ve done. I really feel ike it’s mine. Every time that I’ve asked “Is this okay?” the answer I’m getting back from everyone is “It’s up to you.” And I’m like, “Oh, when did that happen?” Anytime I was selecting which song to workshop, it was because it was my favorite song, and I just couldn’t wait to get it out into the world. I’m doing a countdown like I don’t think I’ve ever done for the release of a project. I couldn’t be more excited.