Chico & Rita
In present-day Havana, Chico, a shoe-shiner, tunes his radio to the Radio Progreso station, which is playing old Cuban hits on a program called Melodies from Yesterday. As he listens, the station begins to play a romantic arrangement of A Taste of Me (Sabor a Mí) by Mexican composer Álvaro Carrillo (1921–69) which causes him to remember his life back in 1940s Cuba. In 1948 Havana, Chico and his best friend Ramón are struggling dandies in a low-life bar. Ramon arranges a double date for the both of them with two American tourists. They take the women to a bar where Chico falls in love with the band's beautiful lead singer, Rita. Chico attempts to talk to her, but an American tourist refuses to let Rita leave him.
Chico and Ramón go to the Tropicana Club with their lady-friends, and sneak in through the performer's entrance. While walking around, Chico sees upon Rita and her gentleman friend arguing. The Maitre d' overhears that Chico is an accomplished pianist and persuades him to substitute for the main event's missing pianist. Chico fills in, playing at first sight a new piece—Ebony Concerto by Igor Stravinsky. Chico, initially nervous, ends up performing the piece with aplomb, to the delight of the band. Rita finally agrees to ditch her date and flee with Chico on Ramón's motorcycle and sidecar, along with the Americans.
After a dangerous chase, the American man finally crashes into a car dealership, and the others escape. Rita and Chico leave the rest of the party and go to a bar where Chico introduces her to bebop music, which she takes up quickly. Afterwards they go to Chico's place and spend the rest of the night together. The next day Rita wakes up to find Chico playing a new composition on the piano, which he names "Rita". As they play and kiss, Juana, Chico's former girlfriend, walks in and picks a fight with Rita. The two women angrily leave Chico, feeling betrayed. However, Chico is still smitten with Rita and begs Ramon to convince her to perform with him for an upcoming radio contest. Ramon pays Rita to sing with Chico but after the contest, Rita leaves Chico without speaking to him. He follows her to the house of a santera, who predicts that Chico will cause her much suffering.
That night, the station announces that Chico and Rita have won a month's engagement at the Hotel Nacional. A few weeks later, Chico and Rita are having great success in their performances. Rita's beauty mesmerizes all the men, which ignites Chico's jealousy. One of the admirers, Ron, asks Rita to his table to discuss business. He offers to take Rita to New York City to make her a star, where jazz and Latin music are a burgeoning scene. However, Rita insists that the offer must include Chico. Meanwhile, Chico has been watching from a distance and becomes jealous, believing Rita wishes to leave him for Ron. Rita attempts to explain that she is fighting for both of them to go to New York together, but Chico storms off. Rita goes to his apartment and waits for Chico, but falls asleep in the courtyard. She is awakened by Chico stumbling home with Juana. Hurt, Rita agrees to go to New York with Ron, alone.
After her departure, Chico becomes depressed and he and Ramon eventually secure the means to go to New York to seek their fortunes as well. Chico and Ramón give Chano Pozo a letter of recommendation they received from his sister in Cuba. Chano is receptive and excited to meet fellow Cubans. However, he is involved in drugs and has a short temper. After discovering he was sold oregano instead of marijuana, Chano attacks the dealer, who later finds him in a bar and kills him. Chico finds work as a party musician, and Ramón as an usher at the Plaza Hotel. At one of his party gigs, Chico runs into a successful Rita again, who is hurt by the racist doubts of her fellow party goers about her upcoming film project.
Chico and Rita run away in her new car and spend the night together again. The next day, Ron locates Ramón and proposes a deal to finance his artist-agency business, as long as Ramon finds jobs to keep Chico away from Rita. Ramón complies with his end of the bargain and signs Chico with Dizzy Gillespie, who gives him a gig in Paris and a European tour. Rita becomes a big film star while Chico finds a new girlfriend in Paris. One morning, while playing "Rita" at the piano, the girlfriend's dog, Lily, comes in and sits by Chico. He decides to change the name of the song to "Lily". Back in New York, despite her wealth and success, Rita is still mistreated socially due to her skin color. While being driven to a set, the radio plays a new Jazz hit that she instantly recognizes as the piece Chico composed for her. She is moved to tears when she learns Chico renamed the song. In New York, Rita goes into a bar and sees Chico playing "Lily".
She waits for him outside the bar and demands to know who Lilly is. He teases her about the mystery female's identity, but finally reveals that he renamed the song after a dog. The two passionately kiss and make up. A paparazzo captures the kiss in a photograph that appears in the newspapers. Chico and Rita agree to marry that New Year's Eve, after Rita's debut in Las Vegas. Chico tells Ramón, who worries that their reunion will ruin his business. Ramón slips a packet of drugs into Chico's coat, which police discover during a search after a raid on his gig at the Palladium in New York. They arrest Chico, and won't let him make a phone call to Rita, who waits in vain in a Las Vegas motel. Chico is soon deported back to Cuba. Upset, Rita becomes drunk before her New Year's Eve performance, believing that Chico left her again. Despite Ron's urging to not "spoil it all now", Rita deliberately sabotages her career by denouncing the racism of the Hollywood industry and the hypocrisy of being a celebrated black artist.
Meanwhile, Chico enters Cuba right at the beginning of Castro's regime, and the new Cuban revolutionary authorities seize his passport. All venues are now forbidden to play jazz because it is "capitalist music." Disappointed with life, Chico gives up music altogether.
Sixty years later, when Chico is shining shoes for a tourist, a young man rushes to him and tells him that a famous young singer and her entourage are eagerly asking for him and his jazz music. He reluctantly agrees to meet them and for the first time in years he plays his music for an audience. The singer asks him to record a song with her and Chico agrees. It becomes a big hit and takes him on a world tour, giving him success for the second time. After the tour, Chico is allowed re-entry into the United States. He searches for Rita, starting in New York. He eventually finds Ron in a nursing home and discovers that his friend Ramón has died and learns Rita is in Las Vegas. He goes there and knocks on her door and she reveals that she has stayed for 47 years in the same motel room, working as the motel's housekeeper and waiting for him. The film ends with their reunion.
romantic, flashback