In 1954, Legrand’s album I Love Paris became an instant hit, selling over 8 million copies and making him an overnight star. He followed with albums like Holiday in Rome 1955 and Michel Legrand Plays Cole Porter 1957. In the late 1950s and 1960s, Legrand worked with the French New Wave, scoring seven films for Jean-Luc Godard and ten films with Jacques Demy. He created the genre of musical in French cinema with The Umbrellas of Cherbourg 1964, the first film musical that was entirely sung. The film earned three Oscar nominations, including Best Original Song for I Will Wait For You.
In 1966, Legrand moved to Los Angeles to work in Hollywood. His friendships with Quincy Jones and Hank Mancini helped him meet lyricists Alan and Marilyn Bergman. In 1969, he won his first Oscar for Best Original Song for The Windmills of Your Mind from The Thomas Crown Affair 1968. He received twelve Academy Award nominations and three Oscars. He also won five Grammys from 27 nominations.
In the 1980s and 1990s, Legrand continued performing with his own jazz trio and led a big band on international tours, accompanying stars like Ray Charles, Diana Ross, Björk, and Stéphane Grappelli who celebrated his 85th birthday in 1992. He also recorded classical albums, including Kiri Sings Michel Legrand with opera singer Kiri Te Kanawa. During the 2000s, he worked mainly in the studio and made international tours.