The cycloid is one of the most intriguing objects in the classical physics world, at once solving the brachistochrone and isochronous curve problems. Historically, the cycloid shape has been employed to great success in many physical contexts. We discuss one such case, presenting the longitude problem as a pathway into an in-depth discussion of the analytical solution of a point mass motion along a cycloid. The classical solution is presented, and the modifications needed for a rolling ball along a cycloid rail are made. A comparison is then made between the two cases, and we show that the difference in most physical cases between the point mass and the rolling ball is at most~7%. Next, an experiment is presented in which the isochronous nature of the cycloid path is tested, to different degrees of success. The results are discussed and several possible origins of the discrepancy between the theory and the experimental results are identified. We conclude with a discussion of skidding and slipless rolling.