There can be times in the life of a preacher when the honor, privilege and opportunity of preaching devolve into the burden, drudgery and obligation of preaching. As a Lutheran pastor of fifteen years, I have found this to be my experience. It was clear to me that this way of being negatively impacts both my experience of a sermon and its preparation and the experience of the hearer. What would be available if instead of being a chore, sermons could become play? My thesis is that shifting a preacher’s relationship of sermon preparation from work to play is faithful, life-giving to the preacher, and life-giving to the congregation. In this paper, I investigate what might be possible if a preacher is able to shift to a playful relationship to sermon preparation and preaching. The theological undergirding of seeking and employing a playful approach to sermons comes particularly from the theological insights of Cynthia Rigby and Jürgen Moltmann. I also explore the proleptic aspect of sermon play. I then explore some practices that can be useful in creating a playful engagement with scripture and the preaching process. A structure for getting into the sermon game utilizing Look Ahead Bible Studies and Scripture memorization is proposed. Current homiletical theory is discussed in light of this playful approach. My context for this endeavor is two Lutheran suburban congregations in San Antonio, Texas and Calgary, Alberta.