In reading Philip Guston and Eduardo Paolozzi’s work through the lens of play, this chapter examines the artists’ studio methods in terms of games strategies. In considering the game as an engagement with “unnecessary obstacles,” Guston and Paolozzi’s processes can be understood to have embraced contradictory forces. It appears that for both artists, a play process was enabled through a push against self-enforced limitations. Both artists can be seen to have employed methods that enabled them to respond, adapt and change paths during an unfolding process. The chapter examines Guston and Paolozzi processes in terms of play, their work has appeared to respond by playing games with interpretation; in effect, the material seemed to toy. In Paolozzi’s case, the volume and wealth of material is ungraspable, while with Guston the ambiguity of the multitudinous meanings that emerge from the artist’s repeated return to a limited collection of forms seems to forever defy interpretation.