A few Decembers ago, I drove under darkening holiday skies and tuned into WMSE for Local Live (12/7/21). I was shocked to hear “Sleigh Ride” sound as if two harmonizing aliens had just discovered the tune and thought it the oddest, most beautiful song on Earth. Several other Christmassy songs, including “Good King Wenceslas” – which I’d never given one, let alone a second thought – hit in a similarly emotional way. I thought, “I guess the holidays are OK!”
That was the first time I heard Milwaukee’s Caley Conway and Ellie Jackson singing together. There was something gorgeous in Conway’s spooky, otherworldly treatments of holiday songs. Fortunately for me and all of Milwaukee, Caley Conway’s gorgeous sounds continue on her 2024 album, Partner, and in her live shows.
Tell us who you’d pick to be a Betty this year!
Caley Conway, who has been creating and releasing music in Milwaukee for over 10 years, recently completed a spring tour through Chicago, St. Louis and beyond. Like most working Milwaukee musicians, Conway holds down several jobs in addition to creating consistently inventive music. Her sound is imbued with indefinable glory, like songs from a lost futuristic hymnal. It’s bewildering to consider Conway running from job to job on a Monday, May 11, only to land in front of an attentive audience at Indeed Brewing for a Small Batch Songwriter Session. But that’s exactly where she belongs: Conway and Ellie Jackson, accompanied only by Conway’s electric guitar, wove their voices together for the better part of two hours, hitting all the songs from Partner as well as a few others.
Before the show, I spoke to Conway about the songs on Partner, reflecting on memories and the Milwaukee music scene.
I was listening to your LP Partner. You have a genuine sound, like a one-woman Mamas & the Papas, but 38 times cooler, with contagiously gorgeous harmonies.
I really appreciate that a lot. That is my friend Ellie Jackson (on harmony). I sing with her a lot and she has her own band, too. Lots of times when I’m working on a song, I’ll try to come up with harmonies, and sometimes I just wait and hear what she comes up with for harmonies. Sometimes I’ll just have my own vocal on a track, harmonizing with myself, too.
The whole album has a great sound. I’m a sucker for harmony.
Thank you. I’m a sucker for harmony, too. I think it’s just the coolest thing.
“Hours in the Day” took me to the future and the past at the same time, like some of the best stuff from Laurie Anderson. There’s an authority to your voice that I really admire, sounding ahead of your time.
I love Laurie Anderson, but I wasn’t trying to channel her. I was channeling an Aldous-Harding-married-to-Willie-Nelson type thing.
On your song “Mazzy,” you sang “I am a child forever.” First, I want to ask: What were you into when you were a little kid? Music, movies, whatever.
I was into the music my parents would play. I remember Jagged Little Pill. I always loved Alanis Morrisette. I was into the Disney stuff, which I reference in “Mazzy.” I kind of have a magical memory that was my parents taking us to Disney World when we were little. I remember rebelling against the Spice Girls and Hanson because they were super huge when I was young. My dad loved Van Morrison, so I was kind of into that. I really liked musicals as a little kid. West Side Story, Hello Dolly, Oliver. I also liked Irish dance music because I was an Irish dancer. My parents played a lot of Aretha Franklin, so she was swirling around in my childhood music experience.
I think musicals are so important when we’re young because we’re receptive. We don’t care that they’re acting and talking one moment then dancing and singing the next.
Yeah, and that’s what happens when you’re a kid. You just sort of break into a song and a dance. iI can be very fluid in that way.
So the line, “I am a child forever.” Is that a thought you ascribe to yourself?
I was reflecting on the act of memory. “Mean mug pigtails, I am a child forever.” I was recalling my kindergarten school portrait that hung in my childhood home for a long time. In the photo, I’m so mad, giving this glare to the camera. I was just sort of free-associating. Sitting in the memory, I just came up with the line.
It’s funny how the images, the few that get chosen to be on the wall in our childhood homes, can do some cementing in our consciousness.
Yeah. You were who you were as a kid, and are you still that same person for the rest of your life? Maybe. Notions like that are sort of fluttering around…
“Singing Never” is a song I really dig. And the video, which was included in the Milwaukee Music Video Show during the Milwaukee Film Festival, really went deep.
Josh Evert is the filmmaker who made the video. He also co-produced Partner with me. We borrowed some picture frames from our friends at Dandy and went into the woods and started looking for shots that would be compelling. As we were doing that filming, Josh saw a visual narrative unfolding in his mind. Editing together, Josh ran it through a VCR, so it has this vintage VHS look. I’m really proud of it. It’s awesome to be able to sit there and witness your own song merge with someone else’s vision to become more than it would be on its own. I feel like the video is really Josh’s piece, and I’m thrilled by it. He really takes the viewer through some kind of other dimension and really complements the sentiment of the song as it means to me.
Any more plans to marry the visual with your music in the future?
I do have a plan to make a video for the song “Love is Sex.”
What other new stuff is in the works for you?
I have a batch of 10 to 12 songs. I’m trying to figure out what the creative parameters will be for the recording and production process for the songs. I’m in the phase of throwing paint onto the walls and hoping the process suddenly occurs to me, and then I’ll feverishly know exactly what I need to do and get going on it.
What should readers know about the Milwaukee music scene?
I think they should know it’s excellent and has been excellent for a long time. There are some great artists and bands that have been making work here for more than one decade. If you’re not going out to shows of people in your community, I think you’re missing out. I think people should challenge themselves to substitute one night of watching Netflix for going out to a show and discovering something. If you’re willing to spend 20 bucks, twice a month, you can discover such great music.
What’s inspiring you right now?
Gardening is actually a big one. I’ve been touring more and more, on the road for most of March. Upon coming back, I’ve been very appreciative of observing the plants coming in at a slow pace. That’s also the same attitude I’m approaching my new demos, trying to be a bit more observant, not force it, not rush it, but cultivate songs. Also, the names of plants are awesome. Every time I read a gardening book, I’m like, this should be a lyric in my song. I’m also continually inspired by other live music that I see. Nothing lights the fire like seeing somebody else perform a great song and be like, “Damn, I wish I wrote that.”
Anything else you want to share?
I consider the music thing a job. It’s a huge piece of how I support myself. I want people to keep in mind how hard a lot of us work to make music pay, to make it a legitimate job. Patreon has been one of the most vital things that has allowed me to put out my work. I like for people to keep in mind that this is a legitimate profession, even if you’re not able to do it entirely full time. I just want to continue normalizing musicians getting paid well for what they do. I also want people to know I am happy to talk about financial stuff when it comes to running a band and your music operation as a business, and they should seek me out if they are confused about how to approach pricing, taxes and things like that.
Caley Conway with Ellie Jackson at Indeed Brewing
The setting at Indeed Brewing is one step beyond intimate, with the artists at arm’s length from the chic yet comfy couches and vintage seats in the Barrel Room at the back of the bar. The room is like a carriage house curated by the coolest designers available. Caley Conway and Ellie Jackson very much belong in this past-future environment, and they quickly sing us into voluntary hypnosis with their harmonies. Their oh-ohs and ahhs in “Singing Never” stretch like the spaghetti we become on the other side of the wormhole that Conway and Jackson’s harmonies create, in a past we’ve yet to outrun. I do believe that a quantum mechanics class on the waning power of memory should feature “Singing Never” and its accompanying video.
“Belly Laughing” continues my obsession with time-lapse, as Conway shares how she wrote the song based on a story written by an 11-year-old. Jackson adds that a youngster recently told her, “Watch this!” and commenced to do a slow-motion hula-hoop maneuver. Conway and Jackson decide this is a good move to do throughout “Belly Laughing,” adding an absurd element of an astronaut’s zero-gravity workout video to an already atmospherically charged song. Imagine the slowest rotation of a human’s lower body set to the line “If I live to be 100, I hope you die at 99 and 364/not one day less, not one day more.” Perfection.
In between sets, I chat with a friendly human who introduces herself as Caley’s mother, and she graciously listens to me enthuse about the mysticism of her daughter’s voice and music. As the break between sets ends, Conway pauses from her congenial conversations with the crowd and threatens to begin set two with Ellie Jackson’s song “Path of Destruction” if Ellie doesn’t return at that moment. Conway laughs and launches into the song just as Jackson enters the Barrel Room. The two swap the original harmonies seamlessly, something they both appear born to do. Their parallel magic act of harmony continues through Jackson’s song, a lovely and warmly menacing reminder to oneself.
“Into the Screen Door” goes up and down the ladder of fear and enjoyment, like looking over your shoulder heading up the basement stairs. Later, when Conway sings the lines “Holding still forever” and “As long as it’s a secret,” I believe her songs to be a knife to open up the sky’s vein. Even without the graceful miracle of Jackson’s harmonies, Conway’s voice holds some implicit knowing, an authority held by infrequent titans like Laurie Anderson and Joni Mitchell. That’s not to say she knows that she knows, but when I close my eyes, it’s known that she knows.
