Jimmy James, whose genuine name was James Casey, was born in Stockton on Tees, a town in northeast England, in the year 1892. His father, a skilled clog dancer who performed at various halls in the Northern and Midland regions, introduced James, then only a young boy, as "Terry the Blue Eyed Irish Boy" in 1904. This marked the beginning of James' career in the entertainment industry, as he took to the stage to perform a song and dance act.
As he grew older, James joined several notable troupes, including Will Netta's juvenile singing group, Jockeys, Phil Ree's Stable Lads, and Clare Lovedale's Ten to One On. He eventually formed his own sketch company and toured the country, playing various roles, including that of a bridegroom who got drunk at his own wedding reception and was subsequently locked out on the wedding night.
In 1929, James' talents were discovered by George Black's agent while he was performing in Sunderland. This led to a London booking at the prestigious Palladium, where he showcased his unique brand of visual comedy, which revolved around drunk routines, including rolling a cigarette around his mouth and contorting his facial features.
Throughout his career, James developed three signature routines: "Drunk," "Chipster," and "The Shoebox," which he performed alongside Gormless Hutton Conyers. The latter routine, which involved a series of hilarious misunderstandings and mishaps, was originally performed by James' son-in-law, Jack Darby, before being taken over by his son, Cass James, and later by Roy Castle from 1956 to 1959.