This is part of our monthly series of interviews with musicians who perform in the Berkshires.
Born and raised in Berkshire County, Jackson Whalan is a rapper and producer who has released six albums, five EPs, and over 100 songs. He has toured extensively, both solo and with a live band. On May 24th, he will release his newest song, a cover of Mac Miller’s “Circles,” which was recorded with Berkshire musician Alanna Sinclair. Additionally, he will perform live on May 26th at The Egremont Barn. Later in the summer, he will have performances at Dream Away Lodge and Bousquet Mountain Day.
I had the opportunity to catch up with Jackson at his Southfield studio to learn about his latest work, upcoming performances, and his vision for the live music scene in the Berkshires. I have lightly edited our conversation for clarity.
In May 2021, my colleague Benjamin Learner interviewed you for an article in Berkshire Magazine. You had just released the album From the Woods. Since then, by my count, you’ve released one full-length album and 30 singles, three in 2024 alone, including “This Hits Different,” “Mindset,” and “Breezy.” It seems like you’ve been quite busy!
Thanks for keeping count. Yeah, I’ve just been releasing singles. I’ve found that it’s a great way to build right now. I’ve been performing when I can, but to be quite honest, it’s been hard to get back on track with my live performance since COVID. I’ve been doing a lot less touring around the country and more in the region, whether it’s here in the Berkshires, New York, or Boston. I’m excited to get back out there again, but I’ve been here in the studio, just finishing tracks and working towards an album. I think eventually I will want to put out another album, but I’m finding that song-by-song is the way to go for me right now.
Do you feel that in this age of streaming, is it less important to have an album drop versus singles?
I think it’s important to drop an album at the right time. I think that because we have access to the stats now, we can see how many streams the first song has and then how many streams the last song has. You don’t want to create based on the statistics of what people are gonna play or not. But as artists, you do want to make sure that your work is heard. When you’re developing and growing, releasing songs can be a great way to make sure that everyone’s listening to that song. It’s different from back in the day. I grew up listening to albums, and I grew up feeling like the album was the only way to listen to music. But I grew up on the cusp of Spotify and before that, the download sites, where it started to become more about the song. But I still love albums. And in 2021, I became a dad and every move you make matters so much more.
“This Hits Different” just hit the streets – it’s a super-upbeat track – can you tell us about it and what it means to you?”
It’s kind of self-referential about the song because it’s just such a different song for me. I got out of my comfort zone to make a faster song, which was so different for me because I’m the kind of person who likes to drive around and nod their head to slower hip-hop and stuff. I have been wanting to make music that people can dance to at a live show, music that gets people up off their seats. I was missing that in my catalog and feeling inspired. Also, I wrote that song because one of my sync licensing agents needed a track that was faster for a commercial. [Note: A sync license, or synchronization license, is an agreement between a music user and the owner of a copyrighted composition that gives the user permission to use the song in a video format.] But then I started really enjoying the process of creating that kind of music. “This hits different” is a saying that people use to describe something as being distinct in a good way. It’s a slang phrase.
I’m not familiar with it.
Yeah. It’s what the young people are saying, right? “This hits different.” Like if you find a pair of shoes that are cooler than another, you say, “these hit different.”
Your music has a range of moods to it – some songs, like “This Hits Different,” are really positive and upbeat, yet you also rap about more challenging things going on in your life and in the community, and world. Still, throughout, you seem to have a positive message, expressing hope, talking about moving forward and achieving goals, and sharing your wisdom – like on both “Mindset” and “Discipline.” Does this reflect your natural state of mind? Are you rapping to your audience or to yourself?
I would say both. When I first started rapping and making music, it was a way to express anger and frustration, and in doing that, I became a generally more peaceful person and a more positive person. So music helped me transform from being angry and frustrated, which was reflected in my music way back then.
Recently, I’ve gotten into music that is about mindset. I think a lot of that has come about because I’ve gotten into things like exercising, meditation, hiking, reading certain books, and things that have helped me to have a better mindset. Seeking out things that help me with dealing with life. And then when I’m making music about it, it’s to help others because it’s helped me, and I’m hoping that I can pass on whatever inspiration I’ve had to other people. When I released my song “Discipline,” there was a girl in Mexico who was a fitness trainer who discovered the song online. She started using it in her social media and talking about how “Discipline” helped her to overcome some of her struggles. That’s the goal as a musician: to reach people in a way where a song could actually help somebody who might be struggling.
I’m wondering if, at times, you’re also trying to lift yourself up?
Absolutely. I think a lot of music and art does that. It could only be for yourself, but hopefully, the byproduct is people feeling better as a result.
What are you working on now?
I just finished a Mac Miller cover of the song “Circles.” And I have a bunch of songs that are unfinished. I have a spreadsheet that is a laundry list of tracks that haven’t been finished. I think it’s so easy to start new music and it’s really tough to finish. I’m going through and finishing song by song. I have a collaboration with an artist named Fatlip, who’s in this hip hop group called The Pharcyde. And I’m getting my live show ready for some shows coming up. I started a new side project that’s just instrumentals called Who-Z.
Named after the town – Housatonic or “Housy?“
Yes, like the town. And that’s for more like beats, just hip-hop beats and stuff. So I’m rolling out tracks under that alias. And yeah, always working on new songs.
Last night, I listened to your soon-to-be-released song, “Circles,” featuring Alanna Sinclair. Can you tell us a little about it? It seems ethereal and a bit different from some of the other music you’ve made.
The song is an example of me wanting to stretch my boundaries and explore new sounds. Alanna came to me wanting to record that cover. When we started the session, I thought I was just recording her. And then she encouraged me to sing on it. It’s very different from my music. If you look at Mac Miller, I feel similar to him in that he has tracks like “This Hits Different.” He has this album called Circles that’s emo, rap, soft rock, even folky, almost. I felt like, well, Mac Miller has this really diverse catalog, so it encouraged me to also branch out and do things that might be unexpected or way out of my comfort zone. And I’m trying to sing more, too, so that was a good opportunity to explore that.
When’s that going to come out?
That’s dropping on May 24th. Right before the show.
That’s a good segue. You have several upcoming shows, including May 26th at The Egremont Barn and June 22nd at Dream Away Lodge. Plus, you are performing in Northampton at Bishop’s Lounge on May 17. What can folks expect at these performances?
I’ll be performing with a live band. I’ll be doing my freestyle rapping with topics from what that audience writes on a whiteboard. I’ll have Tim Morrison on drums, Sam McGarrity on guitar, and Miles Lally on bass, which is a completely new configuration. Maybe some special guests – we’ll see. I’ve been using this piece of gear, the MPC Live, which is a standalone beat machine [Jackson holds up the device – see photo below]. It’s like a drum pad machine, but you can use it without a computer. It’s like its own instrument, which I’ve started using live.
Will you have a band at Dream Away Lodge, too?
Yeah. I don’t know exactly who’s gonna be in that one.
I’ve seen you many times at The Egremont Barn, doing your own sets but also jumping in and freestyling with other bands, from Clare Maloney to Pressing Strings, to Glori Wilder, which was an incredible night – one of my favorite reels I’ve posted on Music in the Berkshires. I’m always so impressed with what you come up with and how you get the crowd into it. Do you enjoy these opportunities to get up there and freestyle with other bands?
It’s definitely one of my favorite things to do. I really enjoy it. On the one hand, I’m not loading in and doing all this stuff – I’m sitting in, and it’s a cameo. When it’s a cameo, I’m putting so much into it. And, with the freestyling, it really is in the moment. You’re drawing from things that are happening right in front of you. Performing with other groups has been so fulfilling. I love getting called up. And The Barn is a great community–it feels like we’re building a real community out here when that happens.
I have to be honest, when I’m engineering sound, it’s sometimes hard to go back to the soundboard after because the artist is now the engineer again. This is part of a larger thing, which is that doing music you have to wear a lot of hats. It’s funny to watch me go back and wear the engineer hat right there. Interacting with crowds in real-time is my favorite thing to do.
Are you ever worried that the words won’t come to you? Is it stressful for you?
When I do the whiteboard freestyle, there are a lot of factors. Sometimes the handwriting isn’t good. It can take me extra time to read the word. Sometimes somebody writes a word just to mess with me, whether it’s an inappropriate word, a word that I’ve never heard before, or very hard to rhyme. If somebody gives me the word “purple,” then I would do a slant rhyme – I would say “circle.” Or if somebody gives me the notorious word “orange,” I would do a slant rhyme like “Florence” or “porridge” or something that people would still see as a rhyme. I think that’s the beauty of rap: you can bend language to make it rhyme, even if it’s not a perfect rhyme. What makes that possible is your flow, your energy, and your interaction with the crowd.
So I love that. And it seems to be that, as an artist, when you find something that works, you want to double down on it. It’s never gone horribly – it’s always gone very well. Whether you’re doing comedy or music or anything on stage, you’re constantly workshopping to see what works and then when you find what works, you want to stick with that and develop it. So that’s what I’m doing with the whiteboard.
The night you joined Glori Wilder on stage at Egremont Barn, you rapped, “I’m gonna get up on the mic and tell you a little story / They asked me if I would engineer sound for Glori / And now we got a crowd here before me / Yo, a lot of people over 40.” It must be so different when you perform here than when you do in NY City. Is there enough of a younger crowd that comes out to see the music that you make? How does that make you feel?
I’m happy that I’m reaching an audience, any audience, really. But the short answer is no, there are not enough young people here. It’s challenging for the people who are here who are young, there’s no central gathering location for live music specifically for young people. And at the same time, I’ve been surprised at The Egremont Barn to see young people out, too, people that you didn’t even expect would be there who are young. You’re like, “Oh, wait, do young people actually live here?” You drive down Main Street in Great Barrington at 11 pm, and the only thing open is the Cove. This area seems to be a place where people come to relax and rejuvenate, and there’s not a nightlife culture here in the same way that there is in other areas and in the same way that there used to be. I think it’s challenging.
Were there venues that used to provide that?
Yes. Through the Railroad Street Youth Project in Great Barrington, we used to throw concerts in the Searles school. We used to throw massive shows in the gym, which I think they just tore down. It was like every young person was there. I was a part of a music festival that happened in the area that we organized called The Big Up. It doesn’t seem like that exists here anymore. When I rapped, “A lot of people were over 40,” it’s not a negative thing, it’s just is what it is. It’s an observation. It doesn’t mean that it’s good or bad at all. I loved growing up here and especially being in this studio. I feel so inspired by having nature surrounding me.
Is there anything you think that can be done to draw younger people out?
I’m excited about The Common or Garden Pub in Housatonic because it’s run by somebody who I grew up with and went to high school with. I think just having somebody who’s running something that’s in their 30s is a good thing. Having more things like that. There is also the economic side of it. It’s really unaffordable for people to live here. I think that that’s a huge part of it, or at least that’s what I’m hearing. It’s hard to find places to rent. There are a lot of factors that make it that way. When you go out to a show in the Berkshires, there’s not a place where you’re going to expect to see a ton of young people.
To my knowledge, there are not many rappers or hip-hop artists in the Berkshires. Do you feel isolated at times?
Yeah, I do feel isolated, but I originally found hip-hop here. People were playing it here. There was a group of rappers who were a generation older than me who showed me how to rap. There used to be more hip-hop here, but there are some people out here doing it, but, yeah, I definitely feel isolated. That’s why it’s important for me to travel.
What keeps you here?
I’ve lived in New York City. I’ve lived in Northern California. I’ve lived in LA. And I’ve traveled, touring a bunch. If I were going to come up with the top five reasons for me to be here, it’d be [Jackson counts on his fingers: One] my family, which includes both my parents. [Two] Nature. [Three] This studio (see photo below), which is next to the pond–it just feels serene to me. And then four would be the community of people who are forward-thinking, whether it’s about food or climate or just caring about certain values – there’s a concentration of those kinds of people here. And then five would be the peacefulness, the quiet, and being able to look up and see the stars.
You recently took a short break from social media? Are you comfortable sharing what led to that?
Yeah. The stuff that’s going on in the world. I just felt overwhelmed by images of violence that were in the Middle East and what’s happening to children. And noticing that I’m distracted. When I’m in the studio, I’ll put my phone across the room just to stay away from it. Now I’m setting a limit on my all social media. I get two hours a day, which kind of seems like a lot, but it’s part of my job. I wanted to recalibrate and focus on my creativity without getting the distraction, because it’s just so distracting and so addictive.
I didn’t get into music because I wanted to share it on social media. I got into music because it was my calling, and it changed my life. I see a lot of artists, including myself, who have been guided into this behavior pattern that includes social media at the expense of creating your best work. And I just want to create my best work. And so I took a two-week break. I feel like as I’m returning to it now, I’m not consuming as much as I used to.
Discipline?
Yeah, it goes back to discipline.
You’ve talked to me in the past about the state of music in the Berkshires. What would you like to see happen here?
A standing room club. And a recurring jam session, something like Producer Mondays in New York City. People coming together and making music in the moment. I’ve considered starting that myself.
Can you tell me about Producer Mondays – what is that?
It’s a live session–everything’s being made up on the spot, in the moment. And there are guests that come up, but it’s not an open mic.
Is it similar to when you did The Sesh at The Egremont Barn last year?
Yes, that was the intention of The Sesh. Beyond what’s going on on stage, it’s an opportunity for everybody in the music industry to be under one roof, connecting with each other, which I really want to see more of here. There are a lot of people doing stuff out here. But things are spread out, and you have to drive everywhere. Having one central thing where we’re all connecting with each other and connecting the dots. There should be zero competitive nature in the music. It should be all of us connecting with each other all the time. And I don’t feel like there is competitiveness here, but we need to be together more and brainstorm and just connect. I was thinking about doing little micro sessions here in my studio. Probably could only fit a few people.
In “Greatness,” you rap, “Who’s this white boy from the woods rappin’ ridiculous running multiple businesses so that the world can witness this.” Have you been able to reach a point where you can make a living off your music career, or do you have to take other jobs/gigs outside of music?
Currently, the only thing I’m doing to supplement my income from music is sound engineering, which, in a way, I’m doing to be at The Egremont Barn, connecting with people and the community. Depending on the month, the answer changes. I want to be as transparent as possible about this, because it’s important, and it’s something that no one talks about. One month, I’ll be flying high because I just licensed my music to a commercial or TV show. And then a few months later, I could be the brokest I’ve ever been, and even in debt. And then the pendulum swings and it’s amazing again. The people outside don’t see any of that. Some people think I’ve made it, and some people who know me a little better might know that I’m struggling. As musicians, we’re trained not to talk about that and to just present as successful, and I think it’s such an important conversation to have.
There is an angst in the song “Greatness” about having to beat the odds. Everyone’s trying to do it, and it’s such a roller coaster. There are a lot of rappers who just act rich and present themselves as rich, and I think it’s more relatable and beneficial to have real conversations about what it’s really like to do music because it takes a million streams to get $4,000. If you’re an artist starting out, and you’re relying on streaming, you’re delusional. Even for me, with 6,000 monthly listeners, that’s not currently enough to sustain any sort of income. And so I have to do sync licensing, sell beats, and merch. There’s a laundry list of income streams, which is great as an artist–you can rely on multiple revenue streams. I see a lot of artists doing really well just from live shows. That’s one way to do it. But with sync licensing, you get paid for work you thought you were doing for free. I have a track that was in a TV show, “All American” on Netflix, and that was a sync license.
Is that a one-time payment, or is there a royalty stream?
Depending on the deal, you would get residuals through BMI or ASCAP as performance royalties in addition to a one-time fee. If you’re working with a licensing company that got you the deal, then they might take a percentage of that fee. Commercials tend to be a one-time payment, which is a larger payment because there’s no back end. But with AI [Artificial Intelligence], people have been talking about this being in jeopardy. You can have AI make a song for you in like three seconds. But the AI is not quite there yet. There’s still so much that is uniquely human about making real music. And that’s why I think real music will always be worth a lot to people.
Who are you listening to these days?
I’m listening to so many artists. I’ve actually been putting on top 40 music to study the pop hits. There’s a song by an artist named Tate McRae called “Greedy,” which I’ve been studying. There’s a big rap rap beef going on right now between Kendrick Lamar, J. Cole, and Drake. I’m not listening to a ton of hip-hop right now. I’m actually listening to a lot of pop stuff.
Is that because it’s what you like, or are you looking for inspiration?
I’m interested in writing pop stuff. Pop-rap stuff.
What are your plans for the rest of 2024?
I am booking more shows right now. I’m looking to perform in the Northeast and beyond. I’m releasing tracks. I really want to put out an album before the end of the year. I’ve been thinking I’m going to do an album, and then I just keep doing songs just because that’s what’s working for me. But I’m also focusing on being a dad, and I’ve been part-time in New York City. I’m going to be spending more time in the city.
Is there anything else that I did not ask that you would like to share with our readers?
Well, first off, I’m really proud of you for creating this platform. It’s important. It’s like the glue that kind of brings the scene together. In this post-COVID landscape, what is the music scene? We’re the ones who define it. I think that there’s so much potential for music in the Berkshires, in general, and I just want to encourage people to go out and support live music and go stream those artists. I want to encourage the artists in the Berkshires to look beyond live shows and how you can make a career work. Whether it’s sync licensing, or growing your streaming numbers, or whatever. I’m thankful for how much potential there is here for music, and I appreciate everybody who’s been open-minded to coming out to my shows, even though my music is very different from a lot of what’s out here.
I’m just grateful–grateful for the opportunity to do music and to have this area, even though it’s not the most hip-hop place there is. It’s inspiring. And I’m thankful for The Egremont Barn – for supporting me in my journey as an artist. So keep going to The Barn! And come out to the shows and check out the new track when it drops.
You can learn more about Jackson at jacksonwhalan.com. His upcoming shows include May 17 @ Bishop’s Lounge, Northampton, MA; May 25 @ Dottie’s Coffee Lounge/Dorothy’s Estaminet, Pittsfield; May 26 @ The Egremont Barn; June 6 @ Brighton Music Hall, Allston, MA; June 7 @ Hawks and Reed Performing Arts Center, Greenfield, MA; June 8 @ Higher Ground, Burlington, VT; June 9 @ Fairfield Theatre Company, Fairfield, CT; June 22 @ Dream Away Lodge, Becket; July 11 @ Groove, New York City; July 20 @ Bousquet Mountain Day, Pittsfield; August 31, Lizard Lounge, Cambridge, MA.
You can find his music on his website and all major streaming platforms, including Spotify, Apple Music, and Amazon. You can also follow him on Instagram and Facebook.
— Mark @ Music in the Berkshires