If a ball is incident obliquely on a horizontal surface and is allowed to bounce more than once, then it is likely to bounce many times before it starts rolling along the surface. The number of bounces before rolling commences depends on the initial vertical speed and the normal coefficient of restitution. The transition from bouncing to rolling is examined using a simple theoretical model and is compared with experimental data obtained by filming the process with a video camera. We find that the final rolling speed is proportional to the initial horizontal speed of the ball and depends on the initial ball spin, but is independent of the tangential coefficient of restitution. Representative videos for different balls are included as supplementary material, including a superball thrown with a backspin that creates a back and forth motion. Instructors could use the experiment and/or analysis for an advanced undergraduate lab or use a simplified observational exercise for non-majors.