Watch soap2day. The Highwaymen - Live: American Outlaws is a box set of concert performances from country music's legendary first "supergroup" featuring Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson. The Highwaymen - Live American Outlaws contains a previously unreleased full-length concert film recorded live at Nassau Coliseum, Uniondale, New York, March 14, 1990 and transferred from the original film reels especially for this collection.