Released during Portland Pride, this episode celebrates one of the city’s most singular performers: Saint Syndrome, Portland’s Miss Gay Pride 2025 and the live-singing, piano-playing drag sensation behind The Queen’s Keys and Keyed Up Karaoke.
Justin sits down with Saint to talk about classical piano, church music, coming out, drag, perfectionism, stage fright, and finding a way to make music feel joyful again. Saint shares how she went from conservatory training and church organ gigs to building a drag career around live vocals, piano-bar shows, musical theater, parody, and queer community.
They also talk about working with Nicole Onoscopi, the origin of The Queen’s Keys, why live music feels different in queer spaces, and what it was like playing piano for Jinkx Monsoon’s stand-up special Red Head Redemption.
This one is full of exactly the kind of gay piano magic you would expect from Portland.
See Saint Syndrome
The Queen’s Keys
Every Friday from 7 to 9 p.m.
Live music, drag, piano, comedy, Nicole Onoscopi, Saint Syndrome, and no cover.
https://ccslaughterspdx.com/
Dueling Pianos
Saint brings drag into the dueling piano world, which she jokes has historically been a much straighter space.
https://www.instagram.com/barrelroomportland
Keyed Up Karaoke
Every Sunday from 7 to 10 p.m.
Live piano karaoke with Saint Syndrome and drummer Kevin Huttman. Former choir kids, theater kids, shower singers, and brave little divas are all welcome.
https://ccslaughterspdx.com/
The Piano Queen Holiday Special
Saint Syndrome and Nicole Onoscopi return with The Piano Queen Holiday Special. VIP tables are expected to sell out, so grab tickets early.
https://www.startheaterportland.com/tm-event/piano-queen/
Connect with Saint Syndrome
https://www.saintsyndrome.com
https://www.instagram.com/saintsyndrome
https://www.facebook.com/saintsyndrome
https://www.youtube.com/SaintSyndrome
https://www.tiktok.com/@saint_syndrome
For booking and inquiries, visit Saint’s website or connect with her on Instagram.
About Saint Syndrome
Saint Syndrome is the lowest bass with the smallest waist, Portland's Miss Gay Pride 2025, and the only live-singing, piano-playing drag sensation. A native of Salem, Oregon, she traded in the classical conservatory for the speakeasy spotlight, and now wows audiences worldwide with her eclectic blend of jazz, musical theater, parody, and original music.
Her unique piano-bar event, Keyed Up Karaoke, regularly attracts local talent and touring Broadway casts. You can see Saint Syndrome on Prime Video and Apple TV+ playing for Jinkx Monsoon's stand-up special Red Head Redemption. Having shared the stage with legends like Latrice Royale, Alyssa Edwards, Plastique Tiara, and other RuPaul’s Drag Race stars, Saint Syndrome is a performer you won’t want to miss.
In This Episode
Saint playing piano at Justin and Daniel’s wedding
growing up in Salem after being born in Hawaii
starting piano at six years old
studying classical piano and psychology in Wisconsin
church music, organ lessons, and coming out in college
leaving a Christian fellowship after being asked to step away from leadership
finding drag through an amateur college show
using drag to make music fun again
getting around perfectionism by being silly on stage
her mom becoming a Saint Syndrome superfan
live-streaming during COVID
how Saint met Nicole Onoscopi
the Judy Garland and Barbra Streisand duet that started The Queen’s Keys
why Bolivia called The Queen’s Keys “Vegas show” energy
moving The Queen’s Keys to CC Slaughters
Keyed Up Karaoke and the magic of live piano karaoke
adding Dierks Bentley to the songbook for Justin
dueling pianos at Barrel Room
why Saint feels like a gateway drug to drag
working with Jinkx Monsoon on Red Head Redemption
falling asleep at the airport after filming in New York
stage fright, mindfulness, and playing with the Oregon Symphony at 16
and the most unhinged thing Saint has ever done in full drag
Mentioned in This Episode
Red Head Redemption
Saint played piano for Jinkx Monsoon’s stand-up special Red Head Redemption, available on Prime Video and Apple TV+.
Jinkx Monsoon
Saint talks about working with Jinkx during the pandemic, playing for livestream shows, performing in Lavender Nights, and later filming Red Head Redemption in New York.
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