After beginning his career with the Rothesay Entertainers in Scotland, Wilson joined the D'Oyly Carte Opera Company, with whom he performed from 1931 to 1937.
[1] In 1931, Wilson joined the D'Oyly Carte Opera Company, at first in the chorus, understudying and occasionally performing the role of the Defendant in Trial by Jury and Ralph Rackstraw in H.M.S.
In 1934, he was given the additional principal roles of Hilarion in Princess Ida and Nanki-Poo in The Mikado and moved up to Leonard Meryll in Yeomen, and Marco in The Gondoliers.
In 1935–36 season, he continued to play the Defendant and shared the roles of Ralph, Nanki Poo, Leonard and Frederic in The Pirates of Penzance.
[1] After this, Wilson became a solo artist, heading his own concert party singing Scottish ballads for several years on tour throughout Britain.