Indian Motorcycle’s Jack Daniel’s limited-edition touring model appeared for the 2021 model year as part of the brand’s annual collaboration with Jack Daniel’s and Klock Werks Kustom Cycles. It was the fifth motorcycle in the partnership series, following earlier Jack Daniel’s special editions built on other Indian platforms. This version used the Roadmaster Dark Horse as its foundation and was positioned as a highly exclusive, factory-built collector’s bike rather than a regular catalog trim. Production was capped at 107 units worldwide.
The design theme was tied to Jack Daniel’s Gentleman Jack, with Whiskey Pearl paint, oakwood-inspired accents, and branded details intended to echo the whiskey’s double-charcoal mellowing and barrel-aging story. Indian also added numbered identification and custom commemorative touches to underscore the limited nature of the build. The model was announced in 2020 for the 2021 model year and was sold through Indian Motorcycle dealers as a special-order limited edition.
This Roadmaster edition belongs to a single, clearly defined production run. Unlike the Jack Daniel’s nameplates that later moved to different Indian models in subsequent years, the Roadmaster-based version did not establish a separate long-running lineage. As a result, it is best understood as one exclusive model-year special edition within the broader Jack Daniel’s/Indian limited-edition series.