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Skylyne Spotlight: Jake Cassman

Inside Jake Cassman’s restless new chapter of humor, heart, and hard-earned rock & roll



When I first came across Jake Cassman’s story, what stood out to me was how much life seemed to sit behind the music. Some artists have a straight-line path into songwriting, but Jake has a much more complex and interesting background that strongly influenced the way he writes and performs. Cassman does an amazing job of combining the honest storytelling of Americana music with the buzzing energy of rock and roll music. He makes songs that can be funny and serious at the time without sounding weird. He delivers the dramatic sound of classic songs that feature the piano but he also comes through with the loud and wild sound of rock music.


His debut solo album, Idling High, marks an important new chapter for him, with the record already earning attention for its urgent, timeless sound, with comparisons to Tom Petty, Counting Crows, and Jason Isbell. His single “October Burning” charted on both Mediabase and CDX AAA radio, giving Cassman his first significant mainstream radio placement as an independent artist. Outside of the studio, Cassman continues to build a creative life that stretches beyond one role - working as a school music teacher, co-writing for other artists, contributing production work to the Vulture music podcast “Switched On Pop”, and has even created award-winning music videos, including a recent winner at the Culver City Film Festival.


With Idling High streaming everywhere, the We All Look The Same music video arriving July 15, and Idling High: Live at Kulak’s Woodshed coming August 24, Jake Cassman enters this solo era with a rare mix of craft, humor, and emotional range. 


This past week, I got the chance to speak with him about the road to Idling High, the many lives that shaped his songwriting, and what this new chapter has opened up for him.



SKYLYNE: For people who are just getting introduced to you through this interview, how would you describe who you are as an artist right now?


Jake Cassman: I just put out my first record under my own name, after five records with my band/project Drunken Logic. I'm a school music teacher by day, and over the years have done just about every gig you can think of -- dueling pianos, weddings, street performing, writing musicals, and more. All of that experience lets me draw on an incredible pool of musicians and a bottomless well of musical influences and inspiration in my music. Now, if I can just get back to actually finishing a song I'm writing! (The writer's block has been real lately).


SKYLYNE: That mix of school teaching, dueling pianos, weddings, street performing, musicals, and Drunken Logic already says so much about the world around your writing. Your new album Idling High feels funny, lived-in, and surprisingly tender. What kind of world were you trying to build with it?


Jake Cassman: I moved to LA in 2018, and knew from the moment I touched down that I wanted to make something in this city's storied folk-rock tradition -- from the Byrds to Tom Petty to Dawes. I also took a lot sonically and thematically from Jason Isbell and Counting Crows, and there's definitely a "country-curious" side to this record. The songs themselves ended up being about laying yourself bare and reexamining your assumptions and habits in the light of a new place and the strange times we're living in.


SKYLYNE: The album honestly kicks, but it also feels really lived-in. When you listen back to it now, does it feel more like a document of a specific time in your life, or more like a version of yourself you're still growing into?


Jake Cassman: In many ways, it's an honest look at the version of myself that I was when I first moved here. And honestly, I kind of wish I was less like that version than I often think I am. I felt frustrated by a lack of progress lately, but that's the curse of being an ambitious, anxious musician to some extent. I spend a lot of time wishing I was further along and a better, more developed person than the one I'm describing in these songs. I think a lot of people can relate to that.


SKYLYNE: That’s really interesting, where do you think that desire to be further along comes from? Is it comparing yourself to other musicians or something more personal?


Jake Cassman: I'd say that I wish I was making more money as an artist, that more of my income came from my original music. Some of that comes from comparing myself to my peers -- it's easier than ever to do in this era of social media -- but the reality is, most of my friends and colleagues and I are in the same boat. Most of it is personal. I'm an ambitious person, and I don't shy away from it. I hold myself to high expectations, and I take pride in it. The downside of that is, when I don't meet those expectations, I can be very hard on myself.



SKYLYNE: That tension between ambition, anxiety, and self-reflection is all over the album in a very human way. You also seem like someone who has collected a lot of strange, funny, very musician-specific experiences over the years. What's one moment that felt random at the time, but now feels like it quietly shaped you?


Jake Cassman: My first job out of college was a dueling piano bar in Boston. I'd been training for months, and one day, one of the full-time players got sick and I got my first full shift filling in for them. Dueling pianos, if you don't know, means sitting at a piano across from a partner who is also at a piano, and you're supposed to play audience requests the entire night -- on this night, we were rotating 5 players throughout a 6-hour shift, 8PM–2AM. At 12AM sharp, I sat down and saw a $20 request for "Best Of You" by Foo Fighters, a song I knew well, and it came with a higher tip than we often get. So I started rocking it hard, screaming like Dave Grohl as best I could -- and as I played, half the audience walked out of the room. It's the single worst feeling I've ever had on stage. At the end of the night, as we were counting our tips, I got multiple compliments about how I'd played that song, so I asked them -- "If it was good, why did everyone leave?" They told me that the subway shut down at 12:30AM and people had to go home. I took from that story that, no matter how much effort you put into your performance, life might happen and a lot of people won't be listening, and that's OK.


SKYLYNE: Haha, That dueling piano story almost feels like a song by itself. When you're making a record, do you usually know what kind of person you are inside that album, or do you only figure that out after it's done? 


Jake Cassman: The reality of the business now is that I have to have the songs ready by the time I go into the studio -- I don't have a label paying for me to hang out and screw around until I find out what I want to say. So usually, I have a pretty good idea of what these songs are, and the version of me I'm singing about, before I go in. This album was slightly different because we went in with 16 songs that were ready, but weren't sure which ones would be on the album -- so there was more self-discovery in the recording process this time than usual.


SKYLYNE:  That makes sense, especially because the record still leaves room for discovery inside songs that were already written. You have this great balance between being genuinely funny and genuinely vulnerable. In real life, do you think humor helps you get closer to people, or does it sometimes help you keep a little distance?


Jake Cassman: It's both. It helps me make a good impression for sure, and make an audience comfortable. But it's also a self-defense mechanism, a means of deflecting from what I'm feeling. So I have to be careful.



SKYLYNE:  That self-defense side of humor comes through in a way that feels honest. Your songs are really self-aware, while still staying warm. How do you keep the emotional part alive when your songwriter brain starts overthinking everything?


Jake Cassman: That's where you need people you trust around you. I'm lucky to have several friends I can send song drafts to, and more who can come in to help play on or produce the record, all of whom have an understanding of who I am and what I'm about. They pull me back into reality if I'm too in my head about something.


SKYLYNE:  I love that idea of trusted people pulling you back into reality. Since these songs eventually have to leave the room and meet an audience, you've played so many different kinds of rooms over the years. What makes a crowd actually stick with you after the show is over?


Jake Cassman: Energy, community, positivity. I don't need a mosh pit or singalongs at every gig (though, to be clear, I absolutely LOVE that). But a room that is actually focused on you and listening to both the music and the words might stay sitting the entire time, and still can give you as much back as a more boisterous crowd. Our album release show at Kulak's Woodshed in North Hollywood -- which we recorded for a live album that's coming in August -- was a wonderful example of this.


SKYLYNE:   That kind of focused listening room seems like it would bring out a different side of a performer. Do you like the version of yourself that comes out onstage, or does that guy still surprise you sometimes?


Jake Cassman:  I've played live so often now that I'm very familiar with that persona, and I've gotten good at reading the room. I can respond to the energy I'm getting from the audience and balance my desire for attention and recognition (let's be honest, it's part of why all of us do this) with my pride in a job well done.


SKYLYNE: I'm curious about the quieter side of being an artist. What does a good creative day look like when no one is clapping, no one is posting, and nothing dramatic is happening?


Jake Cassman: For me, it's all about inspiration. It's about hearing something so clearly and urgently in your head that you feel compelled to expand upon the idea, even if it means staying up all night until you finish it. I like just noodling around on piano or guitar, or dissecting a song I love to see what about it makes it work so well -- but I get the thrills and chills when I finally have an idea that's worth digging into, no matter how long it takes. And mostly, that's just writing the lyrics, chords, and/or melodies down so that you can remember them for later, and chase the spark from your initial idea until I'm just too tired to chase it anymore.


SKYLYNE: Since so much of your process starts with chasing that spark, I'm curious how much the songs changed once other people entered the room. Is there a song on Idling High that changed a lot from the first version to the final version?


Jake Cassman: Like I said, I've usually written and arranged the entire song by the time we go into the studio. But the one that comes to mind is the last track, "I'm Still Here." Originally there was honky tonk, soulful piano throughout the song -- but Mike Post, who co-produced the record, suggested we do a warm synth pad in the intro instead. From there, we added electric piano instead of an actual piano, and that made for a much more interesting collage of textures with the pedal steel and electric guitars we recorded later.



SKYLYNE: That texture shift is such a good window into the smaller choices that shape the record. What's a tiny sound, lyric, or little moment on the album that still makes you go, "Okay, I'm really glad we kept that"?


Jake Cassman: I almost left the song "We All Look The Same" off the album -- it sounded a lot like some of the other tracks on the record, and the rest of the songs weren't nearly as political as that one is. But I was convinced over time to keep it on, and I'm very glad I did, considering what's happening in the country and the world right now. I'll also highlight one lyric from another song called "I Think I'm Happy" that my friend and collaborator Mitch always highlights: "I used to think this planet turned too slowly/Now I'm just glad the damn thing still works." That makes me laugh every time I hear it.


SKYLYNE: That lyric says a lot about how much specificity matters in your writing. I'm always curious about the artists who don't just inspire someone, but actually change the way they hear music. Are there any songwriters, bands, or albums that really rewired your brain?


Jake Cassman: My brother played me Green Day when I was in elementary school -- it was some of the loudest, catchiest music I'd heard up until that time. They played a sold-out show to 47,000 people in San Francisco on the American Idiot tour that was my first concert, and still one of the best I've ever been to -- I decided that night I wanted to be a musician. But I'll also mention Zac Brown Band, whose song "Colder Weather" was the first one that made me understand and appreciate country. There's a lyric at the end of the first verse: "[She] wonders if her love is strong enough to make him stay/She's answered by the taillights shining through the window pane." In that second, I understood the power of specificity in songwriting imagery and storytelling that makes the country tradition so essential, and I've always tried to keep a little of that in my writing, no matter what genre I'm tinkering with in that moment.


SKYLYNE: Wow, that Green Day-to-Zac Brown path says a lot about the range inside your writing. You've been doing this as a working musician for a long time. What advice would you give to younger songwriters who are just starting out and trying to build a life as an indie artist, especially in a place like LA?


Jake Cassman: Don't be pretentious about the opportunities that come your way -- as long as you're playing and writing, you have an opportunity to learn. But also, don't burn yourself out. The freelance life really took a toll on me in my 20's, not just because I was working a lot, but because managing my schedule and worrying over money cost me a lot in stress and time.


SKYLYNE:  Thank you so much again for taking the time to answer these so thoughtfully. To close things out, here's your spotlight: what do you have going on right now, and what should people be looking forward to next?


Jake Cassman: Idling High is out now, and a live version of the album will be out on 8/24. I'll also be dropping new music, lyric, and live videos every two weeks for the next year on my YouTube channel. Thanks so much for talking to me!



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