PICTURED: Andy Wray on the beach in Ventura. Photo submitted

by Susan Monaghan 

At an event showcase for transgender artists four years ago, a young singer-songwriter played a killer set wearing polka-dotted pajama pants. It was the first time he’d ever performed alone. 

Andy Wray, who lives in Ventura, said he’d injured himself the night before the show. 

“The night before, I wanted to eat pasta, and I ended up . . . it doesn’t make any sense, but I kind of burned my butt with pasta water,” Wray said. 

But Anne Blakeley, the event organizer, encouraged him not to cancel his performance. 

“Anne kept saying ‘It’s fine, you can wear whatever you want onstage, I really want you to do this,’” Wray explained. “There’s a video, I’m in these awful pajama pants onstage.” 

Blakeley, the head of Wray’s transgender support group, had started the annual event the year before. 

“It was just so awesome, he did great,” Blakeley said. “I told him . . . ‘your talent is really powerful.’ He has several different genres he can go with, but I was really impressed with his ability to put emotion in the songs he performs.” 

Wray has been playing the guitar since he was 13. His music is generally pop-y, with melodies influenced by folk music. He started writing lyrics when he was 16, the year he began transitioning. 

“When I started writing when I was 16, it was between me coming out to my family and me still trying to accept it myself . . . I wrote eight songs in a month, and that was a really big deal for me.” 

His mom, Lisa Wolfe, a life coach who uses a spiritual approach to mentor personal development and hosts a Facebook group she calls “The Wolfe Pack,” was his biggest supporter. 

“The only reason I’m here right now is because of her, basically . . . my mom was starting to build that  community while I was coming out as trans, so it was just perfect timing for everything.”

Though Wray has written about the experience of being transgender, he is more interested as a songwriter about communicating feelings too difficult to talk about directly. 

“The first few songs that I wrote I think addressed it more. But I don’t write about [my transition] much, just because I’ve always known I was a boy, and I only dressed like a girl for five years, really,” Wray said. “I talk about the emotions that everyone can relate with, it’s never just one community.” 


Wray’s family has influenced his musical work in more ways than one, both as musicians and as enterprisers with a flair for originality. 

In his early childhood, Wray attended Oak Knoll, the Montessori school his mother and grandmother founded in 1997. 

“They started it before I was born, there’s pictures of my mom with a big belly working on building the school and everything,” Wray said. 

His first guitar came from his uncle, Federico “Freddie” Mejia, a famous musician in his own right. 

“My uncle was actually a famous flamenco player, so he bought my brothers’ guitars, and then a few years later I got interested in it as well, because anything my brothers do I think is awesome,” Wray said.

His grandfather was John Chambless, an instructor at the University of Washington who was hailed at the time as something of a champion for the 1960s counterculture. Chambless was also a disc jockey with a history in the blues scene; he and his wife, Dorothy, helped organize the 1968 Sky River Rock Festival, held on an organic raspberry farm 30 miles northeast of Seattle. It was one of the first major rock festivals in America, and took place a year before Woodstock. 

With his grandfather’s help, Wray started to explore blues music when he was 15.

“He knows everybody, he knows every blues musician . . . so when I told him I was into blues music, he got really excited and bought me this great stack of CDs and albums.”

Wray especially admired two of his grandfather’s favorite bands — The Beatles and The Rolling Stones — because of their significance as storytellers. 

“I’ve always loved the storytelling in music,” Wray said. “I like it when they explain the mindset of what the person is going through … It’s a progression of different mindsets and perceiving situations differently.” 


Tone-wise, Wray’s music has experienced a major shift since he started writing. 

“I was going through so much when I started writing songs. I started writing music because that’s exactly what I needed, because I felt so alone, even though I had my mom, there was so much inside me that was hurting,” Wray said. “My songs have definitely gotten brighter.”

Wray is currently working on an album called Road Runner. One of its major themes is grief, inspired by the loss of Chambless, who died when Wray was 18. 

“It’s a story that’s still being written, because I’m still a part of that grief,” Wray said. “It includes five of the first songs I ever wrote, that my grandfather really liked.” 

For more information on Andy Wray and his music, visit andywraymusic.com.