The gaming systems and methods of the present disclosure improve gaming technology by providing a wagering game having a multi-mode bonus game with multiple triggerable award generators. Generally, when a bonus triggering event occurs in various embodiments, the gaming system randomly determines whether to provide a play of the bonus game in one of multiple different modes, such as a first mode and a second mode. In the first mode, the play of the bonus game includes only one activation of only one award generator, such as the most lucrative one. In the second mode, the play of the bonus game includes an initial activation of a different award generator, such as the least lucrative one, and may include additional activations of additional award generators depending on the result(s) of the activation(s) of the award generator(s).