Besides his own projects, he has sung and/or played guitar, piano, flute, analogue synth, melodica, and/or his simple homemade instruments (thumb-reeds and streetsweeper bristle bass) with Eric Chenaux, Sandro Perri, Jennifer Castle, Baby Dee, Doug Tielli, Alex Lukashevsky, Devon Sproule, Kim Barlow, Thom Gill, Michelle McAdorey, John Southworth, Mary Margaret O'Hara, and many others. Since 1999 he has also led The Ryan Driver Quartet / Quintet / Sextet, playing monthly performances in Toronto. Favouring the ballads of the American Jazz Era, as well as most recently those of composer and songwriter Stephen Parkinson, Ryan plays piano and sings in this group featuring some of Toronto's most accomplished and most experimental musicians (Martin Arnold, Brodie West, Rob Clutton, Nick Fraser, and Michael Davidson). Ryan has toured internationally with notable performances at the Angelica Festival of New Music in Bologna, Italy, Heartland Festival in Vevey, Switzerland; Canadian Blast at Trafalgar Square and the Barbican in London, England; Bergenfest in Bergen, Norway; Tanned Tin Festival in Castellon, Spain; and Sound Symposium in St. John's, Newfoundland. Ryan's recorded output is available mainly through Rat-drifting, Barnyard Records, Fire Records, and Tin Angel Records.

"Ryan always sounds like he has come a long way to sing you a song. His voice contains vast North American distances, long cold winters, the endless ugly monotony of the country, which can be broken and dissipated only by beer, love and music. He is always arriving too late or too early, and what he sings about is always to be found somewhere else, somewhere where he's not. Even when he sings jazz standards, the music isn't nostalgic or pessimistic, in fact you can't tell whether he's talking about the past or the future. Soft, sad, determined … the fact that he's here now, singing these songs is, for those that need such things, a sign of great hope."

- Marcus Boon