Popular game shows offer educators the opportunity to develop active-learning exercises that provide students with a real-world connection to analytical reasoning and methods. We describe a classroom assignment developed for quantitative business courses based on the Monty Hall Problem (MHP), a probability puzzle with ties to the long-running television game show "Let's Make a Deal." Through a holistic view of the MHP, we provide instructors with various avenues to use the MHP as a comprehensive experiential learning exercise with multiple opportunities for individual and class discussions and exercises. Instructors adopting our multifaceted approach to the MHP will expose students to myriad analytical tools including probability, decision trees, and Monte Carlo simulation as well as to cognitive biases that can affect the decision-making process. Among the unique contributions of our work is its focus on the commonly held MHP assumptions. Specifically, we challenge students to articulate conditions inherent to the MHP solution and assess their appropriateness in context. By relaxing one or more of those assumptions, and observing differences in solutions, students become attuned to the importance of knowing and assessing conditions that underlie all quantitative decision-making tools.