Sergio Caputo was born in Rome on August 31, 1954. He began performing in Roman clubs while still a university student, most often at the Folkstudio, earned a degree in architecture and worked as an art director at an advertising agency while his music career ran alongside. His first release was a 1978 single, "Libertà dove sei," on the IT label, followed in 1981 by a four-song mini-album on Ricordi.

The breakthrough came in 1983 with Un sabato italiano (CGD), whose title song set the template: Italian lyrics, ironic and a little melancholy, over arrangements built on swing, Latin-jazz pop and the 1950s Italian swing of Natalino Otto and Fred Buscaglione, with Cole Porter and Fats Waller named among his models. The RAI program Mister Fantasy broadcast eight videos from the album, and the follow-up, Italiani mambo (1984), sold better still. That record brought in the American clarinetist and saxophonist Tony Scott, together with drummer Roberto Gatto, keyboardist Danilo Rea and bassists Giovanni Tommaso and Attilio Zanchi. The title song was entered in the Festivalbar contest and remains one of his best-known. In the same year he wrote the Italian lyric for "Susanna," the lead song of Adriano Celentano's album I miei americani, adapted from a Dutch song by VOF de Kunst.

Scott also made the introduction that gave Caputo his most famous jazz credit. According to a 2022 interview, Scott introduced him to Dizzy Gillespie in Milan, the two agreed to work together at the Blue Note in New York, and Caputo followed the trumpeter on tour to Bologna and Barcelona to record his parts. On Effetti personali (CGD, 1986) Gillespie plays trumpet on two songs, "Il pianeta Venere" and "Trio vocale militare," and Discogs also credits him with scat vocals on the opening "Intro." The album's sleeve thanks Gillespie, and Maurizio Giammarco plays saxophone on it.

The late 1980s were his peak years in Italian pop. He recorded the live album Ne approfitto per fare un po' di musica at Milan's Teatro Orfeo (1987), and entered the Sanremo Festival with "Il Garibaldi innamorato" (1987), "Rifarsi una vita" (1989) and, in 1998, "Flamingo." Between them came Storie di whisky andati (1988), made with the help of Sergio Conforti (Rocco Tanica), Lontano che vai (1989), with the English saxophonist Mel Collins, the rock-leaning Egomusicocefalo (1993) and, in 1996, I Love Jazz. Serenadas (1998) reworked older songs in South American arrangements and added three new ones.

After his 1998 tour Caputo moved to California and gave himself over to jazz, working with a quintet. He has described about twelve years of apprenticeship in America, playing San Francisco rooms such as Enrico's Sidewalk Cafe, the Fairmont Hotel and the Top of the Mark, where he became a much better guitarist because he had to lead the band for audiences who did not know his songs. The result was That Kind of Thing (Idiosyncrasy Music, 2003), an instrumental album and his debut as a jazz guitarist. According to Italian Wikipedia it ranked among the fifty most-played albums of its kind on the American radio charts of the time and won Smooth Jazz.com's award for the most-downloaded independent album of 2005.

In 2009 he started his own label, Alcatraz Moon, with the smooth-jazz single "On a Lonely Night" and the live album La notte è un pazzo con le mêhes, recorded with the Sergio Caputo Quintet. In 2013 he remade his debut as Un sabato italiano 30, in a more openly jazz setting with a band of saxophones, piano, bass and drums. Pop Jazz and Love (2015) was sung entirely in English apart from one song, and in 2017 he joined the singer-songwriter Francesco Baccini for Chewing Gum Blues. The unplugged Oggetti smarriti appeared in 2018, Sergio Caputo en France (French versions of older songs) in 2019, and the Gossip EP, credited to the Sergio Caputo Trio, in 2021. He toured Italy in 2023 and 2024 for the 40th anniversary of Un sabato italiano and has continued to release singles, the latest found being "Mi chiamo Gatsby" in May 2026. He is also the author of three books: a novel, Disperatamente (e in ritardo cane) (2008), a memoir of his advertising years, Un sabato italiano. Memories (2013), and La guerra è finita (2016).

Caputo is a songwriter first and a jazz player second. His early records pair conversational Italian lyrics, full of food, drink, travel and ironic romance, with the harmonic language of swing and Latin jazz, played by horns and a rhythm section rather than a rock band. The models named for that sound are Cole Porter and Fats Waller from the American songbook and, at home, the Italian swing of Natalino Otto and Fred Buscaglione. His guitar, rhythm-first on the early records, became a lead voice during the California years. AllMusic files him under pop and rock with an international tag; the jazz content lies in his repertoire, his guest list and his later instrumental and English-language work.