whimsy

Destin Conrad didn’t expect to release a jazz project so early in his career — let alone just a few months after dropping his debut album, “Love on Digital.”

The 25-year-old singer-songwriter, who first made millions of people laugh on Vine when he was a preteen, entered the music industry as a fresh-faced R&B artist, following in the footsteps of the artists he grew up listening to such as Brandy, Musiq Soulchild and Usher. His first official EP “Colorway” (2021) and the slew of bite-size projects that followed were melodic and honest meditations on love, lust, queer identity and simply having a good time.

But during the summer, Conrad found himself gravitating to jazz, the genre he was introduced to in high school when he was enrolled in jazz choir. He was inspired by all of the greats and contemporary work by artists like Vanisha Gould, and decided that it was time for a slight departure in his own sound.

“I feel like it’s always kind of been in me,” Conrad says over Zoom during an off day from his second headlining tour in support of “Love on Digital.” “It’s always been a tool that I never really got to exercise that I knew I really wanted to.”

After a two-week whirlwind in L.A. filled with studio sessions with some of his bucket list collaborators like Gould, trumpeter Keyon Harrold and beloved L.A. saxophonist Terrace Martin, Conrad unveiled “Whimsy,” an 11-track alternative jazz detour. Rich with songwriting tinged with sensual winks, live instrumentation (piano, horn section and drums) and a spoken word interlude by Bay Davis (that is reminiscent of Meshell Ndegeocello), “Whimsy” is a masterclass in following your own intuition and creating freely — a testament to his Cancer sun.

“I think it’s some of my best work actually,” Conrad says, adding that it was the most fun to make, which is evident on tracks like “Whip,” a cheeky double entendre about trading places in the bedroom and “A Lonely Detective,” which explores the life of a man living a double life. “Things that I’ve spent more time on, I don’t feel as connected to, but I really love “Whimsy.”

Conrad, who performs at the Wiltern on Nov. 14, phoned in the day before Grammy nominations were announced to talk about why he was nervous to release “Whimsy,” why he thinks jazz deserves more attention and what he’s still learning about being an artist in the digital age. Little did he know that by the next morning, he’d receive his first solo Grammy nod for progressive R&B album.

Now that your debut album, “Love on Digital,” has been in the world for a few months and you’ve experienced fans singing it back to you at shows, how does it feel to look back on the journey of releasing it?

It’s been amazing. I think it’s made me look forward to putting more music out. I feel like this tour taught me a lot. While making this album, I had touring in the back of my mind, so I’m really excited that it’s being received well. Also, it’s kind of wild that I put out another project a [few] months later but I’m glad I have such cool fans that receive me in a good way.

Speaking of that, you turned around and released “Whimsy” in August. Can you talk about how that all came together and how your single “Wash U Away” inspired it?

I made the majority of it in a two-week span. “Wash U Away” and “Whip” I had, but they weren’t jazz songs. So I had “Wash U Away” in the tuck for years — I think I made it in like 2021 — but we had it replayed by actual musicians because before, it was just a very bare beat. Then the rest of it I made within those two weeks. I also had “The W” with James Fauntleroy and Joyce Wrice already, but same thing — it wasn’t a jazz song. I knew I wanted to make a jazz album. I didn’t know I was going to do it so soon after my debut album, but I was kind of on a wild one and was like “Why not?” But I’m really glad I did it because I feel like my fans really like that album and I really like that album as well. I think it’s some of my best work actually. Things that I spent more time on, I don’t feel as connected to but it’s something that I’m really proud of.

Take me back to those two weeks in L.A. when you starting working on this project. Was it summer time?

It was summertime, yeah. I live in Brooklyn now, so I was like “I’m going to fly to L.A. and stay there for two weeks to knock this project out.” I told my managers, “Get me in with everybody. Here’s my list of people I want to work with. Let’s figure it out.” We flew out Vanisha Gould, who’s one of my favorite jazz musicians. I was so ecstatic that she was down. She’s such a jazz head. She was kind of like “What the f— am I doing? Are they going to kidnap me? I’m just flying out here to work with this random ass R&B singer.” But I’m so glad she came and we low-key became besties. Same with Terrace Martin. I’ve been a fan forever. He’s the G.O.A.T. James [Fauntleroy]. All these people who I was very adamant about working with. And eventually I want to do another jazz [project]. Maybe a “Whimsy 2” and just keep that world alive because I feel like jazz is such a special genre that gets overlooked and it’s something that I really feel passionate about. Especially because I was in jazz choir in high school and it kind of taught me more about soul music and the origins and how there’s so many synchronicities within other genres like gospel, and how R&B and all of them just tie into each other. I think it’s just really cool.

What was going on in your world when you started making “Whimsy?” Were you listening to a lot of jazz at the time?

Yeah, I was listening to a lot of jazz music. I was listening to a lot of Vanisha Gould and I was like, “I need to do this jazz album.” I thought I was just going to start it and be like “I’m not done.” But I was like “No, I’m done. This is it. This is what I have to say.” But yeah, I always listen to jazz. As I said, I was in jazz choir in high school. My jazz instructor Mr. O put me onto hella jazz. He showed me Frank Sinatra and all these jazz standards. I have videos that I’ll eventually show the world of me performing at my jazz Christmas show. I feel like it’s always been within me. It’s always been a tool that I never really got to exercise but I knew I really wanted to. But like I said, I didn’t know I’d make it in two weeks and that it’d be such a quick thing. It was so fun to make. It’s probably one of the most fun projects I’ve made.

You can definitely hear how much fun you were having on tracks like “Boredom” and “Lonely Detective.” I feel like jazz was once viewed as a genre that older people listened to, but that’s been changing within the last few years. It feels like it’s becoming more popular with younger audiences. What do you think about this?

Personally, I don’t think it’s becoming more popular. I would love to be part of some sort of push of making it more of a thing and I feel like a lot of my fans are younger. I’d like to say in my head that I’m helping push the genre forward.

It’s just not super prominent. There’s not a lot of new jazz artists. If you look at the jazz charts, a lot of what’s still charting is like Frank Sinatra [and] Miles Davis. Laufey is one of the newer faces of jazz that I feel like is pushing it aside from like Robert Glasper. But I don’t know. I feel like a lot of the jazz even that I listen to is the older stuff. There’s a very select few of newer jazz artists that I’m like “Yes.” Like Vanisha Gould, a perfect example. I’m obsessed with her. I think she’s one of the most talented musicians that I know, period.

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

Umm I thought about it [but] what I really thought about were the jazz heads. I thought the real, super crazy into jazz people were gonna be like, “This s— ain’t f— jazz” because I do consider it an alternative jazz album. I remember talking to Terrace [Martin] about that because he’s a jazz head and he’s also older than me and he’s been in it for longer. I was telling him [that] I feel like people are going to have s— to say about it because it’s not traditional and I’m not a trained musician. I don’t know how to read music. I just go with my [gut], and he was like, “That’s why it’s so fire. That’s what makes people feel it.” He was like, “I can tell that you’re young and when I listen to this, I hear a 25-year-old,” and I’m like, “Tight.”

You’ve essentially grown up online and in the public eye. How has that evolution shaped the way you see yourself as an artist, and what have you learned about navigating visibility over the years?”

I feel like it’s an advantage. I always talk about that especially with my artist homies. I was an internet baby so I kind of have just a slight advantage because I knew really early how it worked. I feel like I’m still learning how to promote my music because I know how to get on the internet and be an idiot all day. I can do that literally in my sleep, but being an idiot who knows how to promote his music is different. [laughs] So yeah, I’m still learning that. I used to think it harmed me because I was so scared that people wouldn’t take my music seriously. But no, I use it to my advantage for sure.

We’re at a time in music where it’s common for artists to be open and proud about their identity and sexuality without feeling like they need to use coded language. I think of artists like Frank Ocean, Steve Lacy and Durand Bernarr. Can you talk about why talking about your queerness is important to you?

I feel like I’m a pretty honest person in general. I try not to lie and I feel like all I can do really is just keep it a bean. Most of the time, I try to write about my personal experiences and I deal with men, so that’s just my truth [laughs]. I do also write from other perspectives like things that my friends or my homegirls tell me. I don’t always write from my point of view, but when I do, it’s about a man and that’s all I can really do.