Stanley's Gig (2000)

True to its title, this musical pays homage to jazz's golden age as it chronicles a determined ukulele player's struggle to make a living doing what he does best. Recovering alcoholic Stanley (character actor William Sanderson) would like nothing more than to lounge on the beaches of Hawaii, coalescing with the land that created his beloved style of music. To make ends meet in the meantime, however, he finds work in a convalescent home as a music therapist for the elderly. Just about all of the patients are won over by his charm, wit, and uke stylings -- all except for Eleanor (Marla Gibbs), an introverted, misanthropic patient who resists Stanley's overtures toward friendship. After a series of rebuttals, however, he manages to form a tenuous bond with the aging woman, who, in her prime, was a talented chanteuse in the L.A. jazz scene. When Stanley learns why she suddenly and permanently retired from singing at the height of her success, he becomes determined to set up one last show for the smoky vocalist.