This chapter reflects on practical experiments and artistic works that move beyond an approach to musical time that relies on a single overarching grid or time line. Through discussion of their idiosyncratic performance systems, the authors encapsulate their collaborative perspective on the generation of expressive rhythm and groove in live electronic music. They argue that commercial music software, and the meter-dominated music that this often leads to, limits our capacity to experience and appreciate the continuum of rhythmic possibilities. They explain how they have sought to overcome these limitations through the use of proprietary and open tools that embrace both human and machine-generated rhythms.