[9] As a youth, Benson learned how to play straight-ahead instrumental jazz during a relationship performing for several years with organist Jack McDuff.

In addition to his own albums and performances, during this time Benson was a core member of the CTI All-Stars collective both touring and recording.

[15] Benson released a version of "White Rabbit" on the album of the same name in 1972, originally written and recorded by San Francisco rock group Great Society, and made famous by Jefferson Airplane.

Benson's version (notable also for the lush, romantic piano intro and solo by Jorge Dalto), became a huge pop hit and won a Grammy Award for Record of the Year.

[16] (He had sung vocals infrequently on albums earlier in his career, notably his rendition of "Here Comes the Sun" on The Other Side of Abbey Road.

[16] Benson made it into the pop and R&B top ten with the song "Give Me the Night" (written by former Heatwave keyboardist Rod Temperton).

[22] Benson performed at the 49th issue of the Ohrid Summer Festival in North Macedonia on July 25, 2009, and his tribute show to Nat King Cole, An Unforgettable Tribute to Nat King Cole, as part of the Istanbul International Jazz Festival in Turkey on July 27.

In late 2009, Benson finished recording an album entitled Songs and Stories with Marcus Miller, producer John Burk,[23] and session musicians David Paich and Steve Lukather.

[24] As part of the promotion for the album, Benson appeared or performed on The Tavis Smiley Show,[25] Jimmy Kimmel Live!

On October 4, Benson released the album Guitar Man, revisiting his 1960s/early-1970s guitar-playing roots with a 12-song collection of covers of both jazz and pop standards produced by John Burk.

[28] In June 2013, Benson released his fourth album for Concord, Inspiration: A Tribute to Nat King Cole, which included Wynton Marsalis, Idina Menzel, Till Brönner, and Judith Hill.

[29] In July 2016, Benson participated as a mentor in the Sky Arts programme Guitar Star in the search for the UK and Republic of Ireland's most talented guitarist.

[32] Benson stopped touring internationally at the start of 2024 due to ill health, cancelling a series of UK concerts that summer.

[34][35] The album was an abandoned project based on recordings with arranger and conductor Robert Farnon backed by the London Symphony Orchestra from 1989 that were thought to have been lost.