Trans Artist-Activist Ryan Cassata Shares Summer of Pride Mix & Talks Escaping Queer-Phobia

Ryan Cassata
Maxine Bowen

Ryan Cassata

Meet Ryan Cassata. The trans-identifying multi-hypenate -- a singer-songwriter, actor, writer, activist and motivational speaker -- began his career at the age of just 13 by launching a YouTube channel, which now boasts more than 75,000 subscribers. There he began posting songs and vlogs about his life as a transgender man, which led him to join the Long Island speaker circuit "The Safe Schools Team." He continues to give talks to middle and high school students as well as at universities across the U.S. in a bid to bolster trans inclusivity and awareness among today’s youth.

As part of the service, the now-25-year-old tells kids about his journey toward self-acceptance, and the challenges of coming out to his family. The experience has led him to land a numbers of firsts in his career, including becoming the inaugural recipient of the Harvey Milk Memorial Award in 2011 at his high school in Bay Shore, N.Y. (also Milk’s alma mater), the youngest ever keynote speaker at the Philadelphia Trans Health conference in 2012, and the first openly trans performer on the Vans Warped Tour in 2013.

“I grew up feeling different,” Cassata tells Billboard. “I knew I was queer and I was open about it as soon as I knew. Feeling like a complete outsider in my conservative hometown, I felt rebellious and wanted to run and move on. This made me extremely driven to get my music career moving so I could be successful enough to tour and escape my hometown and its queerphobia.”

Cassata did just that, and has since become a true force in the industry -- penning op-eds in The New York Times and Huffington Post, earning support from SiriusXM, BBC Radio 4, LOGO’s New Now Next, The Advocate and more, as well as appearances on CNN, The Larry King Live Show and The Tyra Banks Show. "I haven’t let being trans or queer hold me back in the music industry and I’ve been open and visible throughout my whole career so far," says Cassata. "It all feels like a dream come true to me. I remind myself of how hard I worked to get here, going back to memories of the early days of playing open mics and burning CDs one by one to sell at shows. I try hard to keep myself in the moment so I can enjoy every minute of it."

Following the release of his 2016 LP Shine, Cassata dropped a handful of new singles including 2018's “Daughter” and 2019 cuts "Jupiter" and "Back Down South," with more music earmarked for release later this year.

Cassata has also honed his skills behind the lens: He was the focus of the 2014 documentary film Songs for Alexis -- which screened at Frameline SF, Raindance in the UK, Toronto Hot Docs, DOC NYC and more -- and co-starred in the 2016 indie film Collective: Unconscious, which premiered at SXSW, for which he was awarded with the best breakout performance honor by the Victoria Independent Film Festival. As a model, he's collaborated with brands including Lids, Bonobos and Lull and also served as the official face of TomboyX’s Trans Pride Underwear line earlier this year.

To fete Billboard’s Summer of Pride, Cassata curated a Pride-themed playlist that touches on his alt-rock musical influences growing up, including cuts by T. Rex, Ani DiFranco and more. Give the playlist a spin and check out a reflection from the artist about the set below.

"Before I was old enough to actually escape I found myself immersed in rock n’ roll. I would lay on my bedroom floor and only move to flip the record to the next side. It felt like an act of rebellion because my peers were listening to Top 40 Radio. I refused to at the time. Not wanting to conform, I refused to get an iPod. I had a walkman, a portable cassette player, and a record player. My peers teased me for being “behind the times” but I loved the warm sound of vinyl and I loved classic rock. Being able to hold the actual record in my hands made me feel even more connected to the music.

I spun vinyls of Bruce Springsteen, Led Zeppelin, T. Rex, Aerosmith, The Doors, Jimi Hendrix, Joan Jett, Elton John, Queen…you name it. I heard my realities and feelings echoed in the lyrics and I was pulled in. My rock n’ roll heroes sounded like outsiders and outcasts too. It didn’t matter who was queer or who wasn’t. I heard my feelings validated in their music. David Bowie sung about androgyny in “Lady Stardust.” Joan Jett sung about rebellion and doing things your own way in “Everyone Knows” and “Androgynous.“ Tracy Chapman’s “Talkin’ Bout A Revolution“ made me know that there were others that felt the same passion I felt in the fight for equal rights. “Rocket Man” by Elton John let me know someone else felt like a total outsider. T. Rex’s “Spaceball Ricochet” reminded me that there were other empathetic misfits like me. 

I heard my feelings reflected in Bruce Springsteen’s songs about needing to get out and move on to something bigger and better. Tracks like “Born To Run” “Thunder Road” “Rosalita (Come Out Tonight)” excited me but also made me feel more normal about my own desires and feelings. Bruce’s lyrics “When they said ‘sit down' I stood up” in “Growin’ Up“ made me feel proud to know that I was a rebel and when I saw and heard injustice in my school I wouldn’t let it go, I would stand up for what I believed in and I would make change, which eventually lead to me winning the Harvey Milk Memorial Award upon graduation. 



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I also listen(ed) to Ani DiFranco frequently. The lyrics in “Little Plastic Castle” brought me to tears [“You are, by far, the cutest / But be careful getting coffee / I think these people wanna shoot us.] I heard my fears being sung about…openly. You just want to enjoy getting coffee but it’s dangerous just because you are queer. When I was 16 I just wanted to enjoy a live show but found myself the victim of a hate crime. I realized that being queer in public was too different for the locals. That didn’t stop me though… I kept on playing shows in the scene, I kept being out, I kept building my career, I just became more careful while remaining completely visible.

As I came out as trans, I found other trans guys doing music such as Joe Stevens and Lucas Silveira (of The Cliks) and got obsessed with their music, especially with the song “A Guy Named Joe” and “Oh Yeah.“ Lucas was the only trans guy, let alone trans guy musician, that I saw that wasn’t on testosterone (T). He was also the first openly trans guy signed to a major record label. I realized that there was a space for me in the world as a trans guy musician that wasn’t on T. If I never heard of Lucas I don’t think I would have had the courage to do things my own way…to keep going against the grain, to pursue my career in the way that I did…with hope. 

Some current anthems by openly queer musicians that I am listening to are “Gone” by Los Angeles-local artist Johanna Chase, “The Pop“ by trans-woman-fronted band DreamStates, “I Am Her” by Shea Diamond, “Holy” by King Princess (what a voice and vibe!),  “John Wayne“ by Lady Gaga, “Let Somebody Love You“ by Boy George / Culture Club, “Thinking Bout You” by Frank Ocean, and “ARE WE STILL FRIENDS?” by Tyler, The Creator. These songs are all a staple on my pride playlists.  

I also put the song “Glory” by Common & John Legend on this playlist -- because I feel like it’s an excellent equal rights anthem and it keeps me hopeful and moving forward -- and Macklemore & Ryan Lewis’ “Same Love“ with Mary Lambert -- finally a mainstream hip hop song by a cis-white-straight rapper about accepting queer people. For me it’s definitely proof that the world is changing."



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For more info on Ryan Cassata head here, and catch the singer on tour through the fall.