He joined the D'Oyly Carte Opera Company in 1928 and was initially assigned the small role of Giorgio in The Gondoliers.
In 1931, Flynn added the role of Old Adam Goodheart in Ruddigore and had the opportunity to substitute for Sydney Granville as Private Willis in Iolanthe.
When Walker left the company in 1948, Flynn reacquired the Usher and played the Lieutenant of the Tower in The Yeomen of the Guard occasionally.
[2] After 23 years with the D'Oyly Carte organisation, Flynn left in 1951, moving to America where he and Ella Halman toured with Martyn Green in a series of Gilbert and Sullivan productions presented by S. M. Chartock.
Flynn's roles recorded with D'Oyly Carte included Go-To in The Mikado (1936 and 1950), the Carpenter's Mate in Pinafore (1949), the Usher in Trial (1949), Giorgio in The Gondoliers (1950), and Old Adam in Ruddigore (1950).