The Caretaker was the first of Pinter's plays to bring him artistic and commercial success as well as national recognition. Opening on April 27, 1960, at the Arts Theatre in London, The Caretaker was an immediate hit with audiences as well as critics, receiving mostly favorable reviews. In addition, The Caretaker received the Evening Standard Award for best play of 1960. In the many years since its first production, the play has continued to be the recipient of critical praise. It has been adapted for television as well as film and has seen numerous revivals all over the world, including at least one production with an all-female cast.

The real-world origins of the play lie in Pinter's acquaintance with two brothers who lived together, one of whom brought an old tramp to the house for a brief stay. At the time, Pinter himself had very little money and so identified somewhat with the tramp, with whom he occasionally spoke. Artistically, The Caretaker is clearly influenced in both style and subject matter by Samuel Beckett's 1955 classic Waiting for Godot, in which two tramps wait endlessly for someone they know only as Godot to come and give meaning and purpose to their lives.

Through the story of the two brothers and the tramp, The Caretaker deals with the distance between reality and fantasy, family relationships, and the struggle for power. It also touches on the subjects of mental illness and the plight of the indigent. Pinter uses elements of both comedy and tragedy to create a play that elicits complex reactions in the audience. The complexity of the play, Pinter's masterful use of dialogue, and the depth and perception shown in Pinter's themes all contribute to The Caretaker's consideration as a modern masterpiece.