Singer/songwriter Rachael Sage has spent decades cultivating a career in the arts.

Sage was born in New York and attended Stanford University. She landed a spot at Lilith Fair, which led to the bisexual-identifying performer increasing her LGBTQ+ fanbase, in 1999.

She started her own record label and released music on it while cultivating other artists as well. Her activism has helped many in need, ranging from unhoused youth assistance to raising funds for wildfire relief.

In 2024, she released the album Another Side and this year another record debuts with Canopy in May.

After a recent performance at Space, 1245 Chicago Ave. in Evanston, Sage spoke with Windy City Times.

            Windy City Times: You are based in New York?

            Rachael Sage: Yes, I lived in the East Village for about 25 years and recently moved to Hudson Valley in Upstate New York. It’s a beautiful, creative and artistic community.

            WCT: Have you always wanted to be a performer?

            RS: I have been playing piano and singing since I was five years old. I went to see the musical Oklahoma! as a little kid with my mom. Legend has it that I came home and played the score by ear on the piano, but I don’t remember it. My folks said they knew they had an oddball child on their hands at that point, but they still encouraged me to perform.

            WCT: Do you still play music by ear?

            RS: Yes. I never learned to read music. I eventually learned instruments like guitar and percussion by ear, and I haven’t looked back since.

            WCT: Have you always liked musicals?

            RS: Honestly, I’m not super gung-ho on musicals as a whole, but when they hit me, they can be transcendent. I am a theater artist myself and a trained classical actor. I love Harvey Fierstein’s Torch Song Trilogy, Neil Simon’s work and Shakespeare in the Park.

            WCT: When did you start to find your footing with music?

            RS: When I was in college, I had already recorded hundreds of songs on a four-track that was given to me at my bat mitzvah when I was 12 years old. I definitely knew that I wanted to be a recording artist. I was obsessed with the Beatles and my parents’ record collection too.

            I eventually got into pop/folk music like Ani DiFranco and Suzanne Vega. I began playing coffee houses in the Bay Area when I was attending college, and wrote a song called “Sistersong.” Ani heard it and invited me to go on tour with her. That was a really big break for me.

            WCT: Did she inspire you to start your own label, like she did with Righteous Babe Records?

            RS: She encouraged me to continue on my independent path, so I forged ahead. I had no idea how hard it would be. It’s been 30 years now, and we have put out a dozen artists over the years on MPress Records. It’s been an incredible adventure!

            WCT: Are you playing songs from your recent acoustic album later today?

             RS: Yes, Another Side. That will be about half of my material tonight and the other half will be from my forthcoming album, Canopy. I will be accompanied by the wonderful violinist Kelly Halloran.

            WCT: Where was your video for “The Other Side (Reimagined)” filmed?

            RS: It was when I was on the road in Madrid, Spain and filmed in a plaza. The original video was made with a full band in the studio.

            WCT: Where does your style come from?

            RS: That’s a nice question. I have always been this way. I used to rob clothes from my mom’s closet and I would wear my dad’s sweaters as a dress.

            I have always perceived my body and face as a canvas; it’s another form of self-expression for me. It was probably magnified by my youth when I was a ballet dancer. I could wear makeup while dancing and my style was a form of drag to me.

            WCT: Being an out and proud musician for such a long time, what do you think of the new generation such as Chappell Roan?

            RS: It’s fantastic, of course. When I was growing up there were artists like Indigo Girls and Melissa Etheridge. I’ve played Pride festivals for decades.

            These days it’s less of a story that the person is queer and the focus is on their music. Amen to that, and I love Chappell Roan. She’s creative and a great songwriter.

            It’s about being authentic and being who you are. Why bother with anything short of that? I feel like part of my job is just to be who I am and be proud.

            WCT: When did you come out of the closet?

            RS: When I was 24 years old. There was no “pansexual” back then and no mainstream words, like queer culture. The word queer was a terrible slur at that time. I still don’t feel one hundred percent totally in sync with that term myself, but it’s growing on me. I love that it has been reclaimed and maybe someday the word “bully” could become a positive word, but we are not there yet.

            WCT: Your new album Canopy comes out in May?

            RS: Yes, May 9, 2025, and I just finished a new video for it. It is in line with what we have been talking about. It’s about inclusivity and creating a community together. This might mean taking a person under your wing to help them get through a hard time or just being a listening ear for someone who might need it. We are going to need kindness, compassion and inclusiveness as the days roll on.

            Visit rachaelsage.com for news on the forthcoming record, International tour and unique merchandise.

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