He is best known for his debut novel Saturday Night and Sunday Morning and his early short story "The Loneliness of the Long Distance Runner", both of which were adapted into films.

Like Arthur Seaton, the anti-hero of his first novel, Saturday Night and Sunday Morning, his father worked at the Raleigh Bicycle Company's factory in the town.

[4] He worked at the Raleigh factory for the next four years, spending his free time reading prodigiously and being a "serial lover of local girls".

Influenced in part by the stripped-down prose of Ernest Hemingway, the book conveys the attitudes and situation of a young factory worker faced with the inevitable end of his youthful philandering.

Saturday Night and Sunday Morning was adapted as a film with the same name by Karel Reisz in 1960, with Albert Finney as Arthur Seaton; the screenplay was written by Sillitoe.

[5] Sillitoe's story The Loneliness of the Long Distance Runner, which concerns the rebellion of a borstal boy with a talent for running, won the Hawthornden Prize in 1959.

[12] Sillitoe's long-held desire for Saturday Night and Sunday Morning to be remade for a contemporary filmgoing audience was never achieved, despite strong efforts.

Danny Brocklehurst was to adapt the book and Sillitoe gave his blessing to the project, but Tony Richardson's estate and Woodfall Films prevented it from going ahead.