Ryan Cassata’s New Greatest Hits Album Combines the Personal, Political

”If I’m writing about myself, even love songs, they’re political, and that’s not my choice,” Cassata says

Ryan Cassata is a man of many talents. But after hustling as an independent touring artist for the last 14 years, the Los Angeles-based folk rocker has followed in the footsteps of Elliot Smith, Sleater-Kinney and The Decemberists by striking a record deal with independent label Kill Rock Stars.

They released Cassata’s latest single, “if you ever leave long island,” in February, and are preparing to distribute the 29-year-old’s greatest hits album on vinyl in record stores across the country soon. It’s the most recent culmination of the transgender artist’s admirable work ethic, exemplified by the seven albums he’s already released since age 13 and the 650 live shows he’s already held since he started touring at 15.

“I’m still doing a ton and I always will, because I’m a major workaholic,” Cassata tells LAMag. “But I do have a little bit more time now for art. The label definitely has more resources and connections than I have, so I think being on a label is just like the next step on the way up.”

This next level of his career began in the beginning of March with an intimate, sold-out DIY show at Print Shop LA, where he chose to kick off the tour with his band—guitarist Stephen Spies, drummer Kyle Dombroski and bassist Loren Barnese. They went to Texas to play SXSW (another milestone moment for Cassata), then continued on through Arkansas, New Mexico, Colorado, Arizona and back California. He was back in L.A. to perform at the TransNation Gala in L.A. last weekend and at a Palms Springs Trans Pride celebration. This Friday, he’ll be in Washington, D.C., for the March for Queer and Trans Youth, demanding an end to state-sponsored misinformation on transitioning and gender-affirming healthcare as well as a ban on all forms of conversion therapy, among other issues.

“People around me kept telling me you shouldn’t mix politics with music. And I realized my identity is politicized, so I don’t really have any other choice,” he says. “If I’m writing about myself, even love songs, they’re political, and that’s not my choice. But that’s how it is here.”

His music is intertwined with his anti-bullying and trans rights activism, making him a true folk singer, with a voice urgently needed right now to challenge the political machine mobilizing across the country to propose and pass a frightening number of anti-trans laws. 

Ryan Cassata 2023 Tour poster image
Promotional poster for Ryan Cassata’s 2023 tour

He spoke to LAMag just days before playing that string of shows in states he considers dangerous ground—openly acknowledging the anxiety running through his mind. “Throughout my life, I have experienced violence just for existing,” he says. “Hopefully the wrong person doesn’t see my name on the flier and put it together that I’m trans, because it can be more dangerous.”

“Texas is probably one of the most dangerous,” he adds. “They actually are leading the nation with the most anti-LGBTQ legislation in the country. So, I think just going there, being present there, is very important right now. I will see a lot of LGBTQ youth that really just need to connect and see that you can make it out.”

Cassata’s teenage years thrust him into the spotlight when, back in 2009, he appeared on CNN to discuss his experiencing transitioning. That was followed by an appearance on The Tyra Banks Show and many more media appearances since—as well as motivational speeches at high schools, colleges and conferences across the country.

The importance of his presence—online or in person—is evident in the comment section of any platform he uses to post or promote his work. “As a trans kid you bring me inspiration to keep living and be a trans adult,” wrote one fan on Cassata’s Instagram post announcing the tour. Another fan, who enjoyed Cassata’s most recent single on YouTube, wrote, “Hope you truly know how many lives you have helped. Saved. Just know Ryan, you’re an angel.”

“Part of what I love about Ryan is that he sort of feels like a throwback to that marriage, that strong relationship, between activism and music that was big in the ’60s, ’70s and ’90s,” Kill Rock Stars president Slim Moon tells LAMag. “I just want to help him have a bigger team to help get the music out to people, get the message out.”

The message is pretty simple: Trans people exist, there is nothing wrong with being trans, they have the right to co-exist peacefully with everyone else, and they’re not going to step back into the closets out of which many have already courageously stepped.

Ryan Cassata
Ryan Cassata, Photo by Asher Phoenix

Photo by Asher Phoenix

Cassata delivers that message with punk rock gusto on one of his greatest hits, “Gender Binary (Fuck You).” Its catchy and defiant chorus: “So fuck you / fuck you / fuck you for telling me / to fit inside your gender binary.”

On “We’re the Cool Kids,” another pop punk track speaking directly to his legions of trans fans, he takes a more motivational and anthemic approach: “Cus we’re the cool kids for starting this movement / we’re cool kids, you better get used to it / we’re changing things and we’re leading this movement / we’re gonna prove it, that we’re the cool kids.”

And then there’s his biggest hit yet, “Daughter,” which Cassata wrote for his father, who initially struggled with accepting the transition before becoming supportive. The tender folk pop tune delicately balances his gender identity with compassion for his father’s perception, delivering yet another catchy chorus, “I didn’t change who I am / I’ve always been a man / still it changed your world / but Dad, I’ll always stay your little girl.”

The song has been streamed millions of times on Spotify and viewed millions more on YouTube, but numbers are just one sign of success. Perhaps more importantly, the song is demonstrably healing some of the people who hear it. One trans fan commented on YouTube, “I sang this to my dad when they had a pride talent show and I made him cry tears of joy. He said that he will start calling me Tobias and his son and use my pronouns now.”

It’s those moments, not a record deal, that ultimately make Cassata feel like he’s “made it” in the music business.

“In the early part of my career, I thought when you’re selling out stadiums, that’s when you make it,” he tells LAMag. “I’ve come to realize, it’s not about that. It’s about: Do your songs matter to people? Are people listening to your songs and finding something that carries them or changes them or helps them? And I’ve done that.”


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He’ll keep doing it, too, no doubt playing to bigger and bigger audiences along the way. His spring touring schedule runs through June, when he’ll play a pride festival in West Palm Beach, Florida—a state where Cassata says he’s “most afraid to go.”

“I hear from my friends that are living there what’s going on; stuff that’s not even making it into the news of how dangerous and scary it’s getting there,” he says. 

In wake of Republican Gov. Ron DeSantis signing a bill into law last year that bans LGBTQ+ issues from classroom discussions, that same community is being targeted outside of schools under the guise of child welfare. Drag shows are being surveilled by undercover police, venues face legal repercussions for hosting the events and, earlier this month, the Senate Committee on Health Policy voted to pass a bill making it illegal for doctors to provide any gender-affirming care to transgender youths — a decision the ACLU called “cruel and dangerous.”

“I think the bills that are the most harmful are the ones that are banning gender-related care,” Cassata tells LAMag. “And a lot of those bills are banning it until age 26. I’m someone that got my top surgery when I had just turned 18. I had wanted it for four years before that.”

“I had surgery 11 years ago, and I’ve never had a regret,” Cassata adds. “But a lot of people have killed themselves because they couldn’t get access to the surgery and hormones. So trans surgeries, they save lives, and banning them is literally killing people.”

On the cusp of receiving a Master of Arts in Social Transformation from the Pacific School of Religion, he wants to inspire people to do more than listen to his music or even create their own.

“When people ask me, ‘How do I become a better activist?’ I think my answer now is always learn as much as you possibly can, be as educated as you can, read as much as you can about the movements that started long before you were here, and learn what you can from those,” he says.

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