Cutler began writing songs and poetry in the late 1950s, making the first of many appearances on BBC radio on the Home Service, where he featured on the "Monday Night at Home" programme on 38 occasions between 1959 and 1963. He gained popularity playing songs where he would often accompany himself on either a piano or the harmonium, and this success led to the release of a series of records starting with 1959's "Ivor Cutler of Y'Hup" EP. Cutler appeared in the pop musical film "It's All Over Town" in 1964, and continued to make appearances on the BBC's programmes during the 1960s, and as a result of an appearance on the television show "Late Night Line-Up", he was noticed by Paul McCartney, who invited Cutler to appear in The Beatles' "Magical Mystery Tour" film. In the film, Cutler plays would-be courier Buster Bloodvessel who becomes passionately attracted to Ringo Starr's Aunt Jessie. Following this film role, Cutler recorded an LP, "Ludo" (1967), produced by The Beatles' George Martin, and credited to the Ivor Cutler Trio, made up of Cutler with bassist Gill Lyons and percussionist Trevor Tomkins. The LP, taking inspiration from trad jazz and boogie-woogie, sees Cutler playing the piano as well as his usual harmonium, and is considered the most traditionally musical of all his records. After its release Cutler continued to perform for BBC radio, recording the first of his sessions for John Peel in 1969. Cutler's work on Peel's shows would introduce him to successive generations of fans, and in the early 1990s, Cutler said, "Thanks to Peel, I gained a whole new audience, to the amazement of my older fans, who find themselves among 16-to-35s in theatres, and wonder where they came from."