Despite the prevalence of game-based learning (GBL), most applications of GBL focus on teaching routine skills that are easily teachable, drill-able, and testable. Much less work has examined complex cognitive skills such as computational thinking, and even fewer are projects that have demonstrated commercial or critical success with complex learning in game contexts. Yet, recent successes in the games industry have provided examples of success in game-based complex learning. This article represents a series of case studies on those successes. We interviewed game designers Zach Gage and Jack Schlesinger, creators of Good Sudoku, and Zach Barth, creator of Zachtronics games, using reflexive thematic analysis to thematize findings. We additionally conducted a close play of Duolingo following Bizzocchi and Tanenbaum’s adaptation of close reading. Several insights result from these case studies, including the practice of game design as instructional design, the use of constructionist environments, the tensions between formal education and informal learning, and the importance of entrepreneurialism. Specific recommendations for GBL designers are provided.