Whenever I attempt to describe DC’s talented trio The Caribbean to a new listener, I always struggle to find the right words. Are they post-psychedelic pop? Experimental indie? Weird folk? Off-kilter lounge?

(Photo by Dakota Fine)

The Caribbean (Michael Kentoff, Matthew Byars and Dave Jones) might be the ultimate example of a band that defies easy categorization – and that’s a good thing.

I prefer to simply think of The Caribbean as “a music lover’s band.” The Caribbean’s unique blend of easy melodies, unexpected stylistic detours, odd chord progressions and unusual rhythmic patterns are a delight to listen to, even as the relaxed vibes come with a dose of the unsettling.

It’s been a while since The Caribbean graced listeners with a new full-length (2014’s “Moon Sickness” is the band’s most recent album), but rest assured, the band is very much alive and well and working on some cracking new tunes. The good news is listeners don’t need to wait until the next album is released to hear them — The Caribbean are showcasing them in their live sets.

This is especially exciting news with The Caribbean back at WE FOUGHT THE BIG ONE for a special in-person show at the Marx Cafe (3203 Mt. Pleasant St NW) on Friday, Nov. 5th. I took the opportunity to get in touch with vocalist/guitarist/songwriter Michael Kentoff and ask a few questions about his journey as a DC-based music maker, what it’s like making music in The Caribbean vs his solo work, and what drives him to be a music “lifer.” Read on!

1) Can you tell us a little about your journey as a DC-based music maker? When did you first realize that you wanted to write your own songs?

MK: Not being very good at playing other people’s songs was one motivating factor, but it feels like I’ve always written. Once upon a time, I was going to be a great novelist. Or short story writer. John Cheever. Raymond Carver. But I never liked what I wrote (everything read like John Cheever and Raymond Carver) and once I was finished, then what? Then I was reading an article in Musician Magazine about Suzanne Vega many moons ago and she said something like “the great thing about writing a song is when you’re finished you can play it!” Love that. I always came up with a melody here and there, but it wasn’t until after college that I really focused on songwriting. Suzanne Vega helped.

2) Pitchfork once wrote about The Caribbean: “they have a strange way of constructing songs, from the lyrics on down. Verses have no rhyme scheme, chord progressions seem drawn from a hat. It’s as though the band had all the pieces for comfortable indie pop in its possession but no interest in putting them into a standard order.” What is it that compels you to make songs that sound so wonderfully skewed?

MK: Thanks for the wonderfully. Writing skewed songs is never really the goal – I try to write tight little pop songs that Dionne Warwick might sing, but it never turns out that way. Part of that is because once Dave and Matt get involved, things sometimes tend to get weirder. Also, because I write for an audience of two abnormal people, it never occurs to me what might work for the rest of the world. Whenever I try to guess, the result is . . . less than satisfactory. Also: I’m very ADHD and the group sort of is, too. We’re highly motivated to not ever repeating ourselves, so we’re always pushing outward. And I know that’s my commission as a songwriter. Like I could help it anyway. Ultimately, The Caribbean’s feeling has always been if this already exists in some form, we don’t need to do it. Like KISS, we’re the group we always wanted to see and hear.

3) It’s been a while since The Caribbean put out a full album (2014’s “Moon Sickness”). What can you tell us about the new music that you’ve been recording? Is a new album in the cards?

MK: It HAS been a pretty long time. Whattaya know? Part of that is down to the fact that our label, Hometapes, shut down operations a couple of years ago. But the bigger reason is that, consistent with what I said earlier, the challenge gets steeper and steeper. The standards get higher. By definition, if you avoid repeating yourself, the world of possibilities shrinks little by little. It can be a maddening path to follow, but it’s the only one we want to follow. It’s not fun any other way. Being in a band is not the be-all end-all; creating something new and reaching new people is the prize. It always has been.

We’ve also been working on both new songs and new schematics for what we do live. We have our basic live set up, which is, two guitars, synths, and drums. And another formulation which is guitar and synths. We’re bringing the latter to WFTBO. We decided that it was silly and rather counterproductive to try to squeeze ourselves into a small space when we don’t have to. We have a bunch of different ways of approaching our songs and this gave us an opportunity to explore that. The experiment actually started when the pandemic hit and we didn’t feel like lugging the drums out onto the front lawn. And it was a groovy alternative to how we usually arranged stuff. We like both ways. It’s cool to have two different alignments. And like I was saying, it’s a better use of space. We have a tall drummer and after he sets up, sometimes Dave and I are setting up on the sidewalk.

We did finish a new record (Don’t Go is the working title), but I have no clear idea of when it’s coming out. We need to either find a new label or put it out ourselves. We play a lot of it out live and it sorta smokes.

4) You put out a digital release under the moniker Washington Hebrew in 2017 that showcased your love of samples, loops and remixes. What’s your take on making music as a solo artist versus playing with a full band?

MK: Not as different as you might think. Just a different way of writing and approaching songs. Instead of guitar or piano, everything was written from samples. Instead of just sampling, though, I wrote entirely new pop songs with those samples as a foundation. It was fascinating and cool. I started the project as a treatment for the postpartum depression I felt after Moon Sickness (I always go through that when a new Caribbean record comes out). Like I said, I don’t need to be in a band so much as we hang out anyway, so we might as well make art! Ultimately, I really like playing and working with people I like and who have ideas that are exciting. So, because there’s no one more likable and exciting than me, I enjoyed making the Washington Hebrew record

5) You’ve been making music for a long time. I believe we can safely refer to you as a “lifer.” What keeps you going? Is there a particular source of inspiration that fans the flames of your creativity?

MK: I have no fucking idea. It’s central to my existence. How’s that? I feel like The Caribbean fills an empty space crying out to be filled with something beautiful. Everything fans the flames, Rick. Matt and I have an old saying: Everything’s R&D.

Listen to and purchase The Caribbean’s music on Bandcamp. And be sure to check out The Caribbean’s live show at the Friday, Nov. 5 edition of WE FOUGHT THE BIG ONE in-person (3203 Mt. Pleasant St NW DC 20010) OR online via Zoom. Register for the Zoom link at: bit.ly/WFTBO_CARIBBEAN. The show kicks off at 10pm EST.