George Washington Benson was a working musician before he was old enough for a paper route. He sang in a talent contest at four, played ukulele for tips in a neighborhood drugstore at seven, and by eight was playing guitar in Pittsburgh's Hill District nightclubs until police shut the underage gigs down. At nine, he cut his first sides for RCA Victor's Groove label — "She Makes Me Mad" backed with "It Should Have Been Me." He left Connelley Vocational High School to pursue music full time; decades later, in 1987, Pittsburgh Public Schools gave him an honorary degree to make up for it.

His real jazz education came on the bandstand with organist Jack McDuff, and it was with McDuff that Benson made his debut as a leader, The New Boss Guitar of George Benson (1964, Prestige). It's Uptown (1966) and The George Benson Cookbook (1967) followed on Columbia, and by 1968 Miles Davis had brought him in to play guitar on "Paraphernalia," from Miles in the Sky — a co-sign from the most important bandleader in jazz. Benson spent the early 1970s moving through A&M, Verve, and finally Creed Taylor's CTI Records, where he became a fixture of the CTI All-Stars alongside the same circle of players who shaped Bob James's and Grover Washington Jr.'s careers — he appeared on Stanley Turrentine's Sugar (recorded 1970, released 1971) and Freddie Hubbard's Grammy-winning First Light (1971), plus the CTI all-star live date California Concert - The Hollywood Palladium (recorded 1971, released 1972), alongside Hubbard, Turrentine, Hubert Laws, and others. His own 1974 CTI record, Bad Benson, topped the Billboard jazz chart before he'd ever sung a note on record, and 1976's Benson & Farrell, a co-billed CTI studio album with saxophonist Joe Farrell, rounded out his run on the label.

The turn that made him a crossover name came in 1976, when he signed to Warner Bros. and released Breezin'. The album went triple-platinum and hit No. 1 on the Billboard 200, but the single track that mattered most was "This Masquerade," written by Leon Russell — Benson's first lead vocal on record. It won the Grammy for Record of the Year, one of jazz's biggest crossover-into-the-mainstream moments of the decade, for a guitarist nobody had signed to sing. Breezin' also picked up Grammys for Best Pop Instrumental Performance and Best R&B Instrumental Performance ("Theme From Good King Bad"), and two years later "On Broadway," from Weekend in L.A. (1978), won Best Male R&B Vocal Performance.

He went bigger in 1980. Give Me the Night, produced by Quincy Jones and written largely by Rod Temperton — the same songwriter behind Michael Jackson's "Rock With You" and "Thriller" — became Benson's first single to reach No. 1 on Billboard's Soul Singles chart and peaked at No. 4 on the Hot 100, his highest pop chart position. Benson kept up a run of gold and platinum records through the 1980s (In Your Eyes, 1983; 20/20, 1985; While the City Sleeps..., 1986), and along the way picked up two more R&B vocal Grammys, for "Moody's Mood" (1981) and "Give Me the Night" itself (1981).

In 2006, Benson made a full collaborative record with vocalist Al Jarreau, Givin' It Up — each of them covering the other's signature hit, Benson taking on Jarreau's "Mornin'" and Jarreau taking on Benson's "Breezin'." It won two more Grammys. Benson has ten Grammy Awards in total and was named an NEA Jazz Master in 2009, the highest honor jazz bestows in the United States. He's still recording: July 2024 brought Dreams Do Come True: When George Benson Meets Robert Farnon, a set of previously lost 1989 recordings with the London Symphony Orchestra, and he collaborated with Gorillaz on their 2018 single "Humility." Health issues led him to cancel international touring dates starting in late 2023.

Benson's whole career is a case study in never having to choose between technical jazz-guitar credibility and pop accessibility. His guitar style — clean, fast, octave-doubled lines, a legacy of his years with organist Jack McDuff and his own admiration for Wes Montgomery's octave technique — earned him respect from jazz players before he ever sang a note commercially. What made him a crossover artist wasn't a change in that playing; it was Warner Bros. and Tommy LiPuma putting a microphone in front of him on "This Masquerade" and discovering his voice could carry a pop single as convincingly as his guitar carried a jazz solo. That dual identity — serious guitarist, serious vocalist, willing to work with pop production teams (Quincy Jones, Rod Temperton) without abandoning the jazz vocabulary underneath — is the throughline from Breezin' through Give Me the Night to his 2006 duets with Al Jarreau.