The Entertainer (1957) sought to highlight the spirit of a Britain battered beyond endurance, at the brink of financial and moral bankruptcy. Osborne uses a mixture of the realistic “kitchen-sink” style, of which he was a major proponent, and an innovative post-Brechtian structure with multiple scenes which switch the setting from the Rice family's fairly sordid lodgings, on to the variety-theatre stage. At various times, the audience is either that of a socially-critical play by John Osborne or of a pathetic but intense variety performance. Archie Rice, the entertainer of the title, is one of Osborne's brilliant but partisan, perhaps semi-autobiographical portraits, which characterize his major plays. He is also the embodiment of a kind of heroic failure, a sympathetic figure who was the antithesis of the crushing petit bourgeois society which Jimmy Porter so raged against in Osborne's Look Back in Anger (1956).

Archie is a music-hall performer in an age when the music halls had all but disappeared. He is largely spent, but still sufficiently self-aware to suffer from the knowledge that he is, as he puts it, “dead behind the eyes”. Now shabbily middle-aged, Archie produces and performs in variety shows whose hallmark is a sort of shallow tawdriness, most memorably and symbolically embodied in the person of a nude Britannia in the last scene of the play. The obsolete nature of music hall is pointed up by the neatness and uprightness of Archie's father Billy, who got out of the business in time, leaving Archie to struggle on, a shabby anachronism in a decaying milieu. A younger generation is represented on-stage by Archie's son Frank and daughter Jean, and off-stage by his son Mick, a soldier whose death in action is announced in the course of the play. Unlike Archie and Frank, Jean has some kind of purpose in her life, however scantily fulfilled that purpose may be: her preoccupation with political protest.

There is an elegiac note of protest in The Entertainer, a mournful nostalgia for the Edwardian era, in which music hall had flourished. Partly, this may stem from a feeling that the music hall managed to engage with life in a vital way, which had appealed simultaneously to the working and the upper classes. Jimmy Porter's bilious protestations in Look Back in Anger against Sunday afternoons in the East Midlands can be read as a revulsion against the stifling gentility and social codes of the petit bourgeoisie. Alternatives to that petit bourgeois gentility are here represented by Billy Rice's music hall in the one hand, and Jean's political protest on the other. On the basis of this analysis, though, Archie is trapped. He is a man out of his time – too young for music hall and too old for politics. In a more complex way he is also a man out of his class. Billy had been a successful actor, Jean an employee who is at least solvent. Archie for his part is neither successful nor an employee, but is marooned somewhere in between. His failed attempts at enterprise combine with his diminishing audiences to serve as requiems for a man who belongs to neither the time in which he finds himself nor to any particular class, and whose struggles against his fate have morally destroyed him.

Archie's moral bankruptcy is explored in a number of ways on stage. Having reduced his wife, Phoebe, to a virtual non-person, whose conversation consists of endless pointless chatter, Archie now proposes to leave her without warning. His object in so doing is to contract – perhaps bigamously – a marriage with a much younger woman, with a view to convincing her parents to invest a substantial sum of money to finance a new theatrical venture. It is Archie's father, Billy, who prevents this from happening, and, as a sort of quid pro quo, Billy agrees to return to the stage, in an attempt to prop up Archie's tottering show. This proves to be the death of Billy, one last exploitative twist in a complex allegorical account of British post-war failure.

There is an unattractive quality of raucous self-interestedness and cynicism in all the male characters on stage, from Billy's stereotypically right-wing prejudices, through Archie's blatant amorality, to Frank's caustic discouragement of Jean: “Don't kid yourself anyone's going to let you do anything, or try anything here, Jeannie. Because they're not. You haven't got a chance. . .. You'd better start thinking about number one”. Even less attractively portrayed are the minor male characters of Archie's brother, Bill, and Jean's ex-fiancé, Graham, who are described in a stage direction thus:

There are plenty of these around – well dressed, assured, well-educated, their emotional and imaginative capacity so limited it is practically negligible. They have an all-defying inability to associate themselves with anyone in circumstances even slightly dissimilar to their own.

In the end, it is only Jean who provides any sense of hope for the future: “Somehow, we've just got to make a go of it. We've only ourselves“, a significantly upbeat variation on Archie's earlier theme “We're all out for good old number one”.

The poignant final scene sees Archie faltering in the midst of an execrable and tasteless performance on the variety stage. Phoebe is in the wings to help him put on his coat and hat, and, after a final address to the audience, Archie is gone. This requiem for post-war Britain, then, sees the death of an older, competent generation of performers, the retirement or disappearance of an intermediate incompetent one, the death or emigration of younger men, leaving only the fortitude of young women such as Jean to provide for the country's future. Jean may be less intelligent and articulate than Jimmy Porter is in Look Back in Anger, but she is also less neurotic, less vicious, and more constructive. She is, in fact, a most unlikely Osborne hero. Typically, however, it is not Jean but Archie who is the central figure of the play, and the one with whom Osborne clearly identifies and invites the audience to identify. There may be hope for Britain in the terms of The Entertainer, but its source is, for Osborne, an alien one.

The part of Archie Rice was written for Laurence Olivier, who led an impressive cast in the 1957 production at the Royal Court Theatre. The sympathetic writing and powerful performance may have combined to obscure some of the flaws in Archie's character, his dishonesty, misogyny and homophobia. Indeed, the play overall is more of a requiem for Britain's imperial heyday than any kind of signal of hope for the future. The small ray of hope that is represented by Jean constantly runs the risk of being overshadowed by Archie's larger and more aggrieved character and intellect. At the time of the first production, the play's innovative qualities, strong cast and impressive dialogue (or monologues) interacted with its state-of-the-British-nation allegories to secure considerable influence for both Osborne and Olivier. The play itself has sufficient positive qualities to justify a continuing place in the theatrical canon into the 21st century, but the reactionary nature of some of the views expressed would now almost certainly require more critical handling in production than was the case in the 1950s.