A level-based multiple outcome wagering system is disclosed. The level-based multiple outcome wagering system includes an interactive controller constructed to control a multilevel wagering session, generate a graphical display of a plurality of actionable elements, wherein the graphical display is a representation of a level of a multilevel wagering proposition presented to a user during the multilevel wagering session, display the graphical display to a user, receive the user's selection of a selected actionable element selected from the plurality of actionable elements, and communicate data of the selected actionable element to a process controller. The process controller is constructed to communicate with the interactive controller and determine from the data of the selected actionable element, a chance outcome selected from the group including a prize awarded to the user, an advancement to a next level of the multilevel wagering proposition, and a termination of the multilevel wagering session.