There’s a lot to unpack with The Real Ambassadors, a farsighted jazz musical composed by Dave Brubeck and his wife, Iola Brubeck, and released as a soundtrack in 1962. At the time, the pianist had just broken through to a mass market in 1959 thanks to his album Time Out, as well as the Paul Desmond-penned hit “Take Five.” Instead of playing it safe for white audiences, Brubeck dove headlong into The Real Ambassadors, a wry take on Cold War cultural politics and the scourge of American racism. The show’s historic import more than half a century later is easy to spot, given the stature of the leading man: Louis Armstrong, who portrays a loosely autobiographical character in a tale of diplomatic outreach to a fictional African country called Talgalla. The results were riveting, even if the project got short shrift. Armstrong had his own complex relationship to the burgeoning movement for racial equality. Black audiences began viewing him as eager to please, a grinning relic from the bad old days, and yet his bold intervention during the 1957 crisis in Little Rock made clear his passion on the subject—and his willingness to put principle over career. His searing vocals and trumpet-playing on The Real Ambassadors must be heard in this wider context. “In my humble way, I’m the USA,” Armstrong sings on the title song, “though I represent the government, the government don’t represent some policies I’m for.” “They Say I Look Like God,” with haunting background vocals from the trio Lambert, Hendricks & Ross, ranks as one of the profoundest things Armstrong ever recorded, though it remains a deep cut. This soundtrack, produced by Teo Macero, has been dubbed “the most expensive demo ever made.” It was greenlit by Columbia, even though the show had never been staged and lacked any clear prospects. While The Real Ambassadors did subsequently receive an abbreviated showcase at the 1962 Monterey Jazz Festival, it then fell into obscurity—a fact that lent deeper meaning to its two contemporary revivals (which took place at Monterey in 2002, and at Jazz at Lincoln Center in 2014).