Flynn left the company in 1933, returning in 1934 to play the same roles. During the next five years, he continued playing these small roles and sometimes substituted as Private Willis, Pirate King in The Pirates of Penzance, the title role in The Mikado, and Sir Roderick in Ruddigore. On the evening before their wedding, Halman played Fairy Queen opposite Flynn's Willis. In 1941, he took over Willis from Granville and the Usher in Trial by Jury from Richard Walker.
In 1946, Flynn gave up Private Willis and temporarily traded the Usher for the Foreman of the Jury. 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. Flynn also substituted for Darrell Fancourt on numerous occasions between 1946 and 1951 as the Pirate King, Dick Deadeye in H.M.S. Pinafore, the Mikado, Sir Roderick, and Sergeant Meryll in Yeomen.
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. His roles on this 1952 tour included the Usher, the Carpenter's Mate, and Go-To. The Flynns soon returned to England where they settled in Penrith and were involved with amateur operatic societies.
Flynn died while fishing in the River Eden, in Cumbria.