Americana crooner Cassandra Lewis stopped by for a Live & Direct session on Monday, July 8. WYEP's Kyle Smith interviewed Lewis, and we heard some songs from her upcoming album, "Lost in a Dream."
Set list:
More Like Momma
Lost in a Dream
So Bad
Some Kinda Love
Interviewer: Kyle Smith
Engineers: Thomas Cipollone, Tom Hurley
Their conversation has been edited for length and clarity:
Kyle Smith: We're Live & Direct with Cassandra Lewis today. Lost in a Dream comes out this coming Friday. Your guitar player Trevor is here. You co-wrote that song together, right?
Cassandra Lewis: Yes, that's right.
Smith: The track is called "More Like Mama." We’ll dive into the album and discuss it shortly. You mentioned Dave Cobb, and we'd love to talk about that in a bit. But first, since this is your first time in Pittsburgh, welcome! And congratulations on your upcoming release.
Lewis: Thank you. The city has been very welcoming.
Smith: The city will certainly welcome you with open arms, especially with that voice. Thanks so much for being here. I’d like to explore your beginnings a bit. When people hear your first song from your debut album, which will be out this Friday, they might think you’ve only recently started making music. But it actually began a long time ago. What first interested you in creating music and singing?
Lewis: Childhood trauma. I don’t have a particularly unique origin story compared to many musicians and artists. For me, music became a coping mechanism—a direct path to finding some peace as much as one can as a human being. I fell in love with singers early on. I was influenced by a wide range of artists like Led Zeppelin, Pink Floyd, Patsy Cline, Dolly Parton, and then grew up with 90s divas like Whitney Houston, Celine Dion, and Mariah Carey. This eclectic mix, combined with growing up in a country town, shaped my musical direction.
Smith: I’ve seen you describe your music as cosmic country, but there’s also a lot of soul in it. People often place it under the broader umbrella of Americana, but you’re influenced by a variety of balladeers from the 70s and beyond. How did you start to hone your craft while putting this first record together? I know you released something independently a few years ago, but this will be your first full-length debut.
Lewis: Yes, this is my first major release. The previous record, Always, was indie. I wrote and recorded it just before the pandemic hit. During the pandemic, I worked construction and had some crypto friends help fund the project. After finishing it, I worked on a music video for "Darlin'," one of the songs from that record. That video got sent to Marco Collins in Seattle, who was working for KEXP, and that’s when things started to unfold for me.
For this new record, it’s been a couple of years in the making. Coming out of the pandemic was slow for everyone; we were just trying to get our feet back under us and give music a heartbeat again. I’m really excited for this one to come out.
Smith: Five days until the release!
Lewis: Yes, I’m ready to start on the next one.
Smith: You’ve been living with these songs for a while. A lot of listeners might not realize that you’ve had these songs done and ready for some time. Now you’re out doing a promotional tour before the record comes out.
Lewis: Yes, we’re hitting two states a day for the next six or seven days, and then another radio tour at the end of the month. We’ll have a few days off, but it’s all part of the grind. I’m actually happy to be on the road. There’s a lot of behind-the-scenes work like emails and conference calls that isn’t as glamorous. Having a team behind me for the first time is really important and helpful, though it can be challenging to release control. It’s a valuable learning experience, and we’re all excited to get it done.
Smith: “Lost in a Dream” is produced by Dave Cobb, who is known for producing a lot of big records in country, Americana, and rock 'n' roll. How did you get connected with Dave Cobb?
Lewis: Before I met the management team I'm working with now at Red Light — Bruce Flohr, Mark Cunningham, and Eleanor Cole — I had always wanted to work with Dave Cobb. I admired the work he did with Brandi Carlile, Chris Stapleton, and Sturgill Simpson. It felt more authentic and aligned with the cosmic, almost psychedelic storytelling I was drawn to, combined with that deeply rooted Americana feel.
Once I started working with Bruce and Mark, we all agreed that if we couldn’t get Dave Cobb on board, we wouldn’t proceed and would continue working independently. It was important to me, and there was some traction in the indie world, but stepping into a major label environment was intimidating.
So, Bruce and I arranged a meeting with Greg Needle, the CEO of Elektra. We sort of ambushed him in a parking garage — Bruce had a clever plan. Greg didn’t know he was meeting me, which worked out brilliantly. During the pandemic, we couldn’t meet indoors, so we ended up in the parking garage. I sang three songs for him right there. A week later, I got a call asking me to meet Dave in Nashville immediately, before talking to anyone else.
Smith: That’s such a great story.
Lewis: It was pretty sweet.
Smith: Jumping in front of someone to grab their attention takes a lot, especially with so many people making music and putting things out there. Congratulations on making that connection. Was “Lost in a Dream” one of the songs you performed for Dave?
Lewis: No, “Lost in a Dream” wasn’t one of the songs I performed. All of these songs are mostly brand new. I had started a number of them, but the material on this album is all new.
Smith: Really amazing. Cassandra Lewis is here. The album is “Lost in a Dream.” That song “So Bad” that we’ve been playing really transfers quite well live as well. We are live and direct here, and we heard the title track, “Lost in a Dream.” I know you mentioned a little bit earlier about the symbolism of the album, but what’s the overarching theme of “Lost in a Dream?”
Lewis: At first, I thought it was mostly about repeated narcissistic, codependent relationship dynamics. It has some of those elements, but it ended up being more about self-reflection—about some of the things I bring to relationships and knowing that I need to work on them. I realized that I don’t need someone to save me; I need to save myself. The album turned into more of a forgiveness of humanity and an acceptance of this person, even if I'm still hurt and don’t like them.
Smith: Well, there have been some really great...
Lewis: Hey, I've still got some healing to do.
Smith: Who among us doesn’t? We’re really glad you’re here. Hopefully, you'll be coming back through on a tour for the album. I noticed you went to Savannah, Georgia, to record the record and worked with a couple of other songwriters, Natalie Hemby and Anderson East.
Lewis: Anderson East? Yeah, I wrote the last song with Anderson. It was really cool. We got it done in about an hour. I brought in the idea and some of the melody, and he just took it from there.
Smith: We’ve had him here in our studios before as well. Had you collaborated with a lot of people before, or was this your first dive into that?
Lewis: This was my first time really writing with anyone. I’ve been sort of a loner, moving around a lot and doing my own thing. Writing was very personal and precious to me. But my team encouraged me to make friends and collaborate.
Smith: That makes sense, especially since you were used to writing for yourself and then suddenly had others involved.
Lewis: It can be hard. It was definitely a challenge for me to get into it and feel like I could still maintain my specific style. The lyrics are very personal and specific. It was a challenge at first, but working with the people I ended up with made it easier. They understood me, let me express myself, and supported me through it. I honestly don’t know if I would have managed as well without their support, especially since I moved to Nashville and started writing just three weeks after leaving that relationship.
Smith: So the pressure was on.
Lewis: Definitely. The pressure was intense. But here it is. The album will be out this Friday.
Smith: Thanks again for coming through. “Lost in a Dream” is the record. Cassandra Lewis is here, and Trevor is the guitar player who’s bouncing along. We’re going to get one more song from you from the record. This is called “Some Kind of Love.”
Lewis: Yes, “Some Kind of Love.” This is essentially what I did to make sure my guitar is tuned, with the humidity changes and all. Sorry about that.
Smith: We are live and direct here at the winery this afternoon. Cassandra Lewis and the record “Lost in a Dream” will be out this Friday.
Lewis: You got it. These are all the words I wish you would have said to me before I left, to make it feel like it was something real that happened to both of us. But he didn’t, so I said them for him. Thank you so much, Pittsburgh.