This thesis investigates how street performers entertain passers-by and audience members in exchange for money. Specifically, it investigates how this exchange relationship is accomplished in light of exchange happening outside the routine context of “the market”, where payment for goods and services is ordinarily enforceable. In this regard, this thesis seeks to uncover the ways that exchange in street performance is alternatively organised through donations, and how giving donations are produced and recognised as interactionally relevant and morally accountable actions. To that end, this thesis employs the allied approaches of ethnomethodology and conversation analysis. It empirically examines video recordings of street performances, mostly collected at the Edinburgh Festival Fringe. Three kinds of street performance encounter are considered: these are musical busking, living statue performing, and circle show performing. The order of the discussions of these performances reflects the extent to which the performers explicitly recruit interactional resources —including talk, gesture and material objects—to morally obligate audience members and passers-by to give donations. The main thrust of this thesis is that street performers, passers-by and audience members collaboratively produce and recognise street performances as gifts that should be reciprocated. The street performances are initially freely given, but participation entails indebtedness that in various ways make remuneration interactionally relevant. In this regard, this thesis also explores how money, value and materiality feature in the giving and receiving of donations. This thesis provides new knowledge about how street performance encounters are ordered, how moral obligation is interactionally worked up through the sequential organisation of social actions, and how money donations are exchanged in return for entertainment. It also provides new understanding about how different kinds of street performance encounters share organisationally similar properties for solving the “payment problem”, but at the same time possess properties that are distinct.