Jazz historian Dave Gelly described the promise of Baker's early career as "James Dean, Sinatra, and Bix, rolled into one".

[5]: 169  His father, Chesney Baker Sr., was a professional Western swing guitarist, and his mother, Vera Moser, was a pianist who worked in a perfume factory.

He became a member of the Sixth Army Band at the Presidio in San Francisco,[10] spending time in clubs such as Bop City and the Black Hawk.

[12] Baker performed with Vido Musso and Stan Getz before being chosen by Charlie Parker for a series of West Coast engagements.

Baker won reader's polls at Metronome and DownBeat magazines, beating trumpeters Miles Davis and Clifford Brown.

In 1954, Pacific Jazz Records released Chet Baker Sings, an album that both increased his visibility and drew criticism.

Baker, with his youthful, chiseled looks oft-photographed by William Claxton, and his cool demeanor that evoked breezy California playboy living, became somewhat of a teen idol on top of being a respected, up-and-coming jazz musician.

[9] Hollywood studios saw movie star potential in Baker, and he made his acting debut in the film Hell's Horizon in the fall of 1955.

[15] While there, he also recorded a rare accompaniment for another vocalist: Caterina Valente playing guitar and singing "I'll Remember April" and "Ev'ry Time We Say Goodbye".

[citation needed] In late 1959, Baker returned to Europe, recording in Italy what became known as the Milano sessions with arranger and conductor Ezio Leoni (Len Mercer) and his orchestra.

[18] Baker spent nearly a year and a half in jail, and was later arrested in West Germany and expelled to Switzerland, then France, later moving to England in August 1962.

[8]: 96  At the end of 1965, he returned to the Pacific label, recording six themed albums whose content veered from straight jazz towards uninspired, instrumental covers of contemporary pop songs arranged by Bud Shank.

[8]: 100–101 The following summer, already having reached a low point in his career, Baker was beaten up, probably while attempting to buy drugs,[21] after performing at The Trident in Sausalito.

[8] In 1969, he released Albert's House, which features 11 compositions by Steve Allen, who organized the recording date to help Baker restart his career.

[8] Moving back with his family to his mother's house in San Jose and depending on welfare, Baker was arrested for forging heroin prescriptions.

During the early 1980s, Baker began to associate himself with musicians with whom he meshed well, such as guitarist Philip Catherine, bassist Niels-Henning Ørsted Pedersen, and pianist Michel Graillier.

[9][25]: 102 In 1983, British singer Elvis Costello, a longtime fan of Baker, hired the trumpeter to play a solo on his song "Shipbuilding" for the album Punch the Clock.

The finished film, Let's Get Lost, is a highly acclaimed and stylized documentary that explores Baker's talent and charm, the glamour of his youth now withered into a derelict state, and his turbulent, sensational romantic and family life.

Two accompanying soundtrack albums, one compiling highlights from the height of his fame and one featuring new material that Baker recorded during the filming of the documentary, were released in 1989.

Early on May 13, 1988, Baker was found dead on the street below his room in Hotel Prins Hendrik, Amsterdam, with serious wounds to his head, apparently having fallen from the second-story window.

Chet Baker's personal life was tumultuous, partly owing to a decades-long drug addiction which began in the 1950s and a nomadic lifestyle caused by touring.

[6]: 43–44  In 1954, despite remaining married to Charlaine, he publicly dated French jazz club-goer Lili Cukier (later known as actress Liliane Rovère) for 2 years, introducing her to others as his wife.

[38][6]: 102  A photo of the couple taken by William Claxton appears as part of a collage on the cover of Chet Baker Sings and Plays.

[6]: 132  The couple posed for a photograph by William Claxton, where Halema appears in a white dress and rests her head on Baker's knee.

[39] In a scandal heavily scrutinized by Italian tabloids, Halema was sent to prison for smuggling jetrium from Germany to Italy for her husband, though she claimed that she was unaware that she was breaking the law.

To his wife's humiliation, by the time of the trial, Baker had already started publicly dating Carol Jackson, a showgirl from Surrey.

After being detained for six months,[8]: 86  Halema returned to Inglewood, and their marriage essentially ended, though they remained legally married for several years because tracking down Baker for divorce proceedings was too difficult.

[49] Other biographies of him include James Gavin's Deep in a Dream—The Long Night of Chet Baker, and Matthew Ruddick's Funny Valentine.

[1] The 1960 film All the Fine Young Cannibals, starring Robert Wagner as a jazz trumpeter named Chad Bixby, was loosely inspired by Baker.

American singer/songwriter David Wilcox included the tender biographical portrait Chet Baker's Unsung Swan Song on his 1991 album Home Again.