On 3 September 1658 the death of Oliver Cromwell thrust the dilemma of succession onto the Privy Council; that day they declared Oliver’s eldest son, Richard, Lord Protector. In the weeks and months that followed, the challenge of imagining, celebrating, and legitimating this unprecedented succession would be taken up by those writing on the event of Oliver’s death and Richard’s accession. This chapter addresses the dilemmas facing those who would fashion Cromwellian celebrity and succession by focusing on a small pamphlet of funerary verse, Three Poems Upon the Death of his late Highnesse, issued in the spring of 1659, rather late in the season of mourning. The volume itself presents a number of puzzles—formal, bibliographical, and imaginative—that can be read both as an emblem of the contradictions of Cromwellian rule—present and absent Oliver Cromwell—and of the anxieties that lay ahead when Three Poems finally appeared.