Destin Conrad didn’t overthink his first jazz project — that’s exactly why it works

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Destin Conrad wasn’t planning on releasing a jazz album so soon in his career, especially not just months after his first album, “Love on Digital,” came out.

The singer-songwriter, now 25, first gained popularity as a young teenager on Vine, making millions laugh with his short videos. He then launched his music career as an R&B artist, inspired by the singers he admired growing up – like Brandy, Musiq Soulchild, and Usher. His debut EP, “Colorway” (2021), and the projects that followed were filled with honest and melodic songs about love, desire, exploring his identity, and enjoying life.

During the summer, Conrad started listening to a lot of jazz – a genre he’d first discovered in high school jazz choir. Inspired by both classic jazz musicians and modern artists like Vanisha Gould, he decided to experiment with a slightly different sound in his own music.

Conrad explains that songwriting has always felt natural to him. Speaking remotely while on tour for his album ‘Love on Digital,’ he says he always felt he had a talent for it, but hadn’t had the chance to fully develop it until now.

Following two busy weeks in Los Angeles collaborating with dream partners like Gould, trumpeter Keyon Harrold, and saxophonist Terrace Martin, Conrad released “Whimsy,” an 11-song album that blends alternative jazz with a unique sound. The album features heartfelt songwriting, real instruments like piano, horns, and drums, and a spoken word piece by Bay Davis that echoes the style of Meshell Ndegeocello. “Whimsy” showcases Conrad’s artistic freedom and trust in his own creative instincts – a reflection of his personality.

Conrad believes this new work is some of his best, and he particularly enjoyed the creative process. You can hear that fun in tracks like “Whip,” a playful song with a double meaning about intimacy, and “A Lonely Detective,” which delves into the complexities of a man with a secret life. Surprisingly, he feels most connected to this project because of its spontaneity – he says he often feels less attached to work he’s labored over for a long time, but he’s especially proud of “Whimsy.”

Jon Batiste, playing at the Wiltern on November 14th, recently discussed his anxieties about releasing his album “Whimsy,” his belief that jazz is an underappreciated genre, and the challenges of being an artist in today’s digital world. The day after the conversation, he received his first Grammy nomination as a solo artist – for Best Progressive R&B Album.

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With your first album, “Love on Digital,” out for a few months and fans now singing your songs at concerts, what’s it like reflecting on the whole process of creating and releasing it?

This has been a fantastic experience, and it’s really motivated me to create more music. I learned so much on this tour, and it’s great to see people enjoying the album, especially since I was already thinking about touring while I was making it. It’s also incredible to be able to release another project so soon and have such supportive fans who appreciate it.

Following up on that, your song “Whimsy” came out in August. Could you tell us about the process of creating it and how your single, “Wash U Away,” played a role in its development?

I created most of the album in just two weeks. I had a couple of tracks, “Wash U Away” and “Whip,” already, but they didn’t fit the jazz direction I was going for. I’d actually written “Wash U Away” back in 2021, but we had musicians re-record it to build it out from a simple beat. Everything else came together in those two weeks. I also had “The W” with James Fauntleroy and Joyce Wrice, but it needed to be reworked to fit the jazz sound. I knew I wanted to make a jazz album, and I decided to do it quickly after my first album – I was feeling inspired and thought, ‘Why not?’ I’m really happy I did, because my fans seem to love it, and I’m really proud of it too. I actually think it’s some of my best work. Surprisingly, I feel more connected to this album, even though I spent less time on it, than to projects I labored over for longer.

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Honestly, what drives me is seeing Black children happy and hopeful. I want to create opportunities for them – things they can be excited about, dream big with, and really grow into as they get older. It’s about helping them see a bright future and giving them a place to be a part of something amazing.

Let’s go back to when you first began working on this project – those two weeks you spent in Los Angeles. Was it during the summer?

It was summer, and I decided to fly from my home in Brooklyn to L.A. for two weeks to focus on a project. I asked my managers to arrange collaborations with a specific list of artists I admired. We brought in Vanisha Gould, a jazz musician I love, and I was thrilled she agreed to participate. Initially, she was a little hesitant about working with an R&B artist she didn’t know, but we quickly became close friends. The same happened with Terrace Martin, who I’ve been a huge fan of for years – he’s incredible. I was really determined to work with all these talented people. I’m already thinking about doing another jazz project, maybe a sequel to ‘Whimsy,’ to keep that musical style alive. I think jazz is a really special genre that doesn’t always get the attention it deserves, and I’m very passionate about it. Being in jazz choir in high school taught me a lot about soul music, its roots, and how connected it is to genres like gospel and R&B – it’s all really intertwined, and I find that fascinating.

When you began creating “Whimsy,” what was happening in your life, and were you heavily influenced by jazz music at the time?

Lately, I’ve been really into jazz – especially Vanisha Gould. It just made me realize I had to make a jazz album. I initially thought it would be a long process, something I’d constantly be tweaking, but I quickly realized what I wanted to say musically and just… finished it! Jazz has always been a big part of my life, actually. I was in jazz choir in high school, and my amazing instructor, Mr. O, introduced me to so much incredible music – Frank Sinatra and all the classics. I even have videos of me performing at a jazz Christmas show that I’ll share someday. It feels like this music has always been inside me, a part of my toolkit that I hadn’t fully explored. I just didn’t expect it to come together so quickly – it only took two weeks! Honestly, it was one of the most enjoyable projects I’ve ever worked on.

The energy really comes through on songs like “Boredom” and “Lonely Detective” – you can tell you were enjoying yourselves! Jazz used to be seen as music for an older generation, but that’s been shifting lately. It seems like more young people are getting into it now. What are your thoughts on that?

I don’t really see it gaining popularity right now, but I’d love to help change that. A lot of my fans are younger, and I like to think I’m contributing to the evolution of this type of music.

New jazz artists aren’t really breaking through right now. If you look at the charts, you still see a lot of classic artists like Frank Sinatra and Miles Davis. Laufey is a newer artist who’s helping to revitalize the genre, moving it beyond artists like Robert Glasper. Honestly, I mostly listen to older jazz. There are only a few new artists I really love—Vanisha Gould is a great example. I think she’s incredibly talented, one of the best musicians I know.

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How did you feel about dropping “Whimsy”? Were you nervous about how people would receive it?

I was worried about how serious jazz fans would react to my album. I figured they might not consider it “real” jazz, since it’s not traditional. I discussed this with Terrace Martin, who’s a seasoned jazz musician, because I wanted his perspective. I explained that I was concerned people would criticize it, especially since I don’t have formal musical training – I can’t even read music! I rely on my instincts. But he told me that was the good part – that’s what would make it connect with people. He said he could tell I was young when he listened to it, and that it sounded like the work of someone in their twenties, which I thought was great.

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The British R&B artist insists her success isn’t simply due to a viral video of her kissing Kehlani, another R&B singer. It’s about more than just that moment.

Growing up with the internet and always having people watching has been… interesting, to say the least. As a movie lover who also creates, it’s really changed how I think about my work. I’ve had to learn how to deal with attention – the good and the bad – and figure out what truly matters to me creatively, separate from what others might expect. It’s been a big learning curve, honestly, figuring out how to stay true to myself while also being seen by the world.

I think growing up with the internet actually gives me an edge, especially when talking to other artists. I basically learned how it all works from a young age, which is a real benefit. I’m still figuring out the best way to promote my music, but being so comfortable online definitely helps – I could spend all day messing around on the internet, honestly! It’s different, though, knowing how to promote your work effectively. I used to worry that my internet background would make people not take my music seriously, but now I see it as a definite advantage and I’m using it to my benefit.

Musicians today are increasingly comfortable and open about who they are, including their identities and sexuality, without needing to hide behind metaphors or subtle hints. Artists like Frank Ocean, Steve Lacy, and Durand Bernarr come to mind. Could you share why it’s personally important for you to express your queerness through your work?

I consider myself a pretty honest person and always try to tell the truth. I mainly write about what I know and my experiences with men, and that’s just my reality. Sometimes I write from the perspectives of my friends, so it’s not always about me, but when it is personal, it usually revolves around relationships. That’s just what I’m most familiar with writing about.

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2025-11-11 14:34