This dissertation considers certain similarities and intersections between poetry and laughter. Baudelaire, in his essay on the comic, describes laughter as being struck from perpetual collisions. Such collisions, I argue, animate many of our best poems, built as they are on clashes and counterpoints. Chapter One examines the traditional theories of laughter (superiority, incongruity, and relief) and describes how they contribute to difficult laughter, the collision of the laugh and the gasp. The chapter concludes with a discussion of two difficult comedians, Archilochos and Richard Pryor. Chapter Two considers two comic strategies, misdirection and excess, that may lead to difficult laughter. I track the reversals and feints of Philip Larkin, Jack Gilbert, and Wendy Cope; then I analyze the comic excesses (intentional and unintentional) of Russell Edson and William McGonagall. The strategies of misdirection and excess come together in the work of John Berryman, the subject of Chapter Three. A line from Berryman's Dream Song 384 gives the dissertation half of its title, and Berryman's comment on Dream Song 29 (“whether the end of it is funny or frightening, or both, I put up to the listener”) stands at the center of my project. Chapter Four looks at two of Berryman's heirs, James Cummins and Joe Wenderoth, each of whose work enacts a series of comic collisions. Chapter Five explains how the study of difficult laughter may prove beneficial in a classroom setting. Throughout the dissertation I tip my top hat to W. C. Fields, who said he never saw anything funny that wasn't terrible. In the intersection of the funny and the frightening, the “ho ho” and the “oh no,” poetry's power resides.