Legendary jazz trumpeter and singer Chet Baker’s life is explored. Early acquaintances recall Chet’s natural ability to memorize songs and play the trumpet with a lyrical, romantic tone. Photographer William Claxton felt he had discovered Chet when he photographed the musician’s first recording session at Columbia Records. Claxton describes Chet’s good looks and charisma as “star quality.” Dick Bock, founder of Pacific Jazz Records, recalls Chet’s early appearances at Los Angeles, California, nightclubs with saxophonist Gerry Mulligan as the best experiences listening to jazz he ever had in his life. At the time, Chet was in his early twenties and had not yet discovered heroin. Jack Sheldon, who met Chet at fifteen years old, notes Chet’s womanizing ways, and says he once stole a girl from Sheldon’s arms without her noticing. Chet remembers the “rude awakening” of hearing Dizzy Gillespie for the first time when he was in the Army, stationed in Berlin, Germany, and playing in the Army band. He was eventually honorably discharged from the Army when he feigned mental illness. His playing came to represent the “cool jazz” sound of the West Coast that was often shunned by East Coast jazz players. In 1954 and 1955, he was named best jazz trumpeter by Downbeat and Metronome magazines, and in 1954, tied with Nat King Cole for best male vocalist. Chet’s longtime on-and-off girl friend Diane Vavra recalls seeing him as a “Greek god” when they first met. However, she soon discovered his manipulative ways, and learned that heroin addicts can never be trusted. In the early days of his career, Chet appeared in the 1955 motion picture Hell’s Horizon and nearly starred in a film about his life, but was arrested and went to Europe instead. The film, titled All the Fine Young Cannibals, was released in 1960 and starred Robert Wagner in the lead role of trumpeter “Chad Bixby.” Chet’s mother, Vera Baker, states that Chet would listen to the radio as a young child in Oklahoma and learn songs by ear. His father, a musician who had been forced to change jobs during the Depression, bought Chet’s first trumpet from a pawnshop when the boy was eleven years old. Chet went on to be married three times: first to a woman named Charlaine, from the Compton neighborhood of Los Angeles; then to Halema Alli, a Pakistani woman, with whom he had a son named Chesney Aftab Baker; and finally to Carol, an English woman he met in Italy, who remained married to him despite estrangement, drug addiction, and numerous love affairs. Carol moved to his home state of Oklahoma to raise their three children, Paul, Dean, and Missy, who acknowledge their father’s habit of dropping in for visits without notice, and joke that he should send them money. Although Carol blames Ruth Young, Chet’s girl friend in the 1970s and early 1980s, for his downfall, Ruth claims she met Chet at a terrible time in his life. He had just started playing trumpet again after a 1968 attack in San Francisco, California, where he claims a group of African American men mugged him on his way to a drug dealer’s apartment, knocking out his teeth in the process. Ruth disagrees with Chet’s version of the story, and alleges the attackers were hired by someone with a rightful vendetta against him. Chet did not play for the next three years, and feared that it might not be possible with dentures. However, Dizzy Gillespie eventually arranged a three-week gig for him at the Half Note in New York City, where he met Ruth. Diane Vavra describes her on-again-off-again relationship with Chet, who abandoned her after a brief reunion in 1977, then came back in 1982 after breaking up with Ruth. They have since maintained their relationship, despite Chet’s physically abusive tendencies. Ultimately, Diane laments that a relationship with a heroin addict is a “no-win situation.” Ruth, who came from a highly connected Hollywood family and was twenty-two years old when her love affair with Chet began, admits that he drained her finances. However, as an aspiring singer, she felt that living with Chet was her opportunity to witness “greatness.” Chet’s wife, Carol, dated British actor Terence Stamp before meeting her husband. She recalls difficult times in their marriage, including having to go on welfare when Chet wasn’t making enough money. She notes that their relationship really began to disintegrate in 1975, when Chet was allowed to return to certain European countries and began working there more often. When their son, Dean, was hit by a drunk driver, Carol was crushed that Chet did not call home after receiving the news. At fourteen years old, Chet’s daughter, Missy, once went looking for her dad at Ruth Young’s home. When no one answered, she broke in and stole some of Chet’s records and awards, in addition to jewelry that she knew Ruth considered valuable. Director Bruce Weber asks Chet about his children, and Chet remarks that none of them are really into music, although he has heard that his eldest son, Chesney Aftab, has a good singing voice. He repeats the advice he has tried to impart to them: find something that brings you joy, and learn to do it better than anyone else. In his fifty-seven years, he estimates he has recorded nine hundred songs, yet he still wishes he could have access to a piano to work on his music. Weber asks what kind of high Chet likes the most, and he answers that he prefers “speedballs,” which combine cocaine and heroin. Diane travels with Chet to the Cannes Film Festival in the south of France, where Chet performs. At a nightclub, he becomes irritated by the chatty crowd and asks for silence before singing his last song, “Almost Blue.” Later, Weber apologizes that Chet’s methadone has run out, and promises he has arranged for more at their next stop in Amsterdam, Netherlands. He asks Chet if he will look back on the making of the documentary as a good time. Chet groggily responds that it has been a dream. A title card notes that Chet died in Amsterdam on May 13th, 1988, at the age of fifty-eight.