From 2014 to 2016, he received critical acclaim as an Artist-In-Residence at Buddies in Bad Times (the world’s largest and oldest LGBTQ theatre complex). His theatre work includes assisting director Brendan Healy on Little Pretty & the Exceptional at Factory Theatre; the original company, remount, and subsequent tour of lemonTree Creations’ dance-theatre hybrid “MSM [ men seeking men]”; the musical “Ragtime” opposite Mark Cassius; and creating and performing ”MacArthur Park Suite: A Disco Ballet” with Nicole Rose Bond. His solo show "#KanderAndEbb" has toured internationally to critical acclaim, and in 2015 his show "Starry Notions" was recognized with several 'Best of Fringe' and 'Outstanding Performance' citations at the Toronto Fringe Festival. Notably, Ryan is one of only a few people to have been in both the movie version (as a hed-head) and a stage production (as Hedwig, becoming the first black actor to play the role) of HEDWIG & THE ANGRY INCH. His long association with Pride Toronto has included hosting the opening ceremonies, performing an hour-long concert for an audience of 4000 at World Pride 2014, and several years as emcee of Blockorama. Ryan’s 2008 Nuit Blanche installation in collaboration with Will Munro and Ina unt Ina set an Attendance Record at the AGO. He is the recipient of the prestigious $10,000 Steinert & Ferreiro Award from Community One Foundation, EGALE Canada’s 2010 History Month honor, an Arts & Culture recognition from The City of Toronto, and is a previous Mississauga Citizen of the Year.