Cavaliers, Clubs, and Literary Culture is centered around the lives and poetry of Sir John Mennes (a naval officer) and his friend James Smith (a debauched cleric) in Stuart and Interregnum England. It explores the largely uncharted territory between the official culture of the court and the often oppositional culture of the city by examining the clubs of city wits, stage actors, and would-be courtiers that flourished during the early and middle years of the seventeenth century. Employing a wealth of untapped manuscript and print sources, Timothy Raylor traces the careers of two struggling poets during the 1630s and sketches their milieu. Mennes's and Smith's involvement with important theatrical and literary figures (including Philip Massinger, Robert Herrick, Sir William Davenant, Sir Kenelm Digby, and Sir John Suckling) is established. The membership, activities, and character of their dissolute fraternity, the Order of the Fancy, are discussed for the first time. Raylor shows that the burlesques and travesties that are generally seen as a Restoration phenomenon had their origins in this earlier milieu. Furthermore, the politicization of this primarily frolicsome mode is traced to a paper scuffle of the 1630s - a disagreement over a controversial attempt by a translator of Puritan sympathies to render Ovid's Heroides into a bourgeois idiom. The outbreak of war in the British Isles ended the social life of fraternities like the Order of the Fancy. But throughout the war and after the royalist defeat there were recurrent attempts to preserve the ethos of the clubs through the sending of burlesque verse epistles. Royalist exiles even attempted to hold club-like meetings on the Continent. During the Interregnum Mennes and Smith were actively involved in royalist subversion, and their verse was first published at this time as part of a royalist propaganda effort. The Restoration saw both men handsomely rewarded, and their verse provided the model for a new generation of wits. But for Mennes and Smith, as for many old royalists, the new regime marked the end rather than the restoration of an era. Despite superficial continuities, a sense of fundamental difference emerges, in the conflicts in the Restoration Navy Office between Pepys, the rising civil servant, and Mennes, the aging dilettante, and in the increasingly cynical and skeptical tone of the Restoration burlesques, which modeled themselves on the verse of Mennes and Smith. This book offers a new reading of cavalier culture, drawing attention to the continuities (and discontinuities) between Caroline and Restoration culture, and sheds new light upon the condition of the production and circulation of poetry in seventeenth-century England.