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Directed by John Holland, this 84-minute film focuses on Gillespie's 1985 visit to Cuba, some 40 years after the pioneering trumpeter first infused American jazz with Afro-Cuban rhythms. It had been more than 30 years since his last visit, but the political situation had finally loosened up enough for Gillespie to go back to the source by participating in the fifth annual International Jazz Festival of Havana. When Gillespie arrived, he was rightfully treated as a musical giant, evident from his private visit with Fidel Castro and the public reverence of Cubans old and young. Always the reciprocator, Gillespie spent much of his visit reconnecting to Cuba's vibrant rhythms and common cultural roots, and the best moments in the film are when he breaks down those rhythms and explains how Cubans were able to sustain connections to African tribal cultures because the drums, so central to both music and spirituality, weren't banned there in slavery days as they were in America. When Gillespie talks about music, it's always from the inside. Gillespie's also a playful innocent, a delightful storyteller and something of a sly stand-up comedian; his explanation of the source of the wind that billows his cheeks to blowfish proportions combines all three elements. Still, many of "Night's" tales are overly familiar, and as the film meanders between anecdote and performance, one longs for tighter editing and a more inventive structure to augment rather than undermine Bill Megalos's excellent cinematography. On the musical side, there are full-blown performances of "A Night in Tunisia" and "Manteca" (with saxophonist-clarinetist Sayyd Abdul Khabyr sounding more enthusiastic than Gillespie), some familiar stage shtick and a little too much of Gillespie vocalizing. There are also several engaging encounters with Cuban trumpeter Arturo Sandoval and a pulsating undercurrent of Afro-Cuban polyrhythms that wordlessly explain Gillespie's 40-year fascination and why this particular visit was very much a spiritual homecoming.
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