In 1985 Benson and guitarist Chet Atkins went on the smooth jazz charts with their collaboration "Sunrise", one of two songs from the duo released on Atkins' disc Stay Tuned. In 1992, Benson appeared on Jack McDuff's Colour Me Blue album, his first appearance on a Concord album. Benson signed with Concord Records in 2005 and toured with Al Jarreau in America, South Africa, Australia and New Zealand to promote their 2006 multiple Grammy-winning album Givin' It Up. He played during the second Monsoon Cup in Terengganu in 2006 and also Malaysia's 50th Merdeka celebration alongside Jarreau in 2007. In May 2008, for the first time Benson took part in the Mawazine Festival in Morocco.
To commemorate the long-term relationship between Benson and Ibanez and to celebrate 30 years of collaboration on the GB Signature Models, Ibanez created the GB30TH, a very limited-edition model featuring a gold-foil finish inspired by the traditional Japanese Garahaku art form. In 2009, Benson was recognized by the National Endowment of the Arts as a Jazz Master, the nation's highest honor in jazz. Benson performed at the 49th issue of the Ohrid Summer Festival in 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 the fall of 2009, Benson finished recording a new album entitled Songs and Stories, with Marcus Miller, producer John Burk, and session musicians David Paich and Steve Lukather. As a part of the promotion for his recent Concord Music Group/Monster Music release Songs and Stories, Benson has appeared and/or performed on The Tavis Smiley Show, Jimmy Kimmel Live! and Late Night with Jimmy Fallon.
Benson toured throughout 2010 in North America, Europe and the Pacific Rim, including an appearance at the Singapore Sun Festival. He performed at the Java Jazz Festival March 4–6, 2011. In 2011, 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 overseen by producer John Burk.
In June 2013, Benson released his fourth album for Concord Records, Inspiration: A Tribute to Nat King Cole, which featured Wynton Marsalis, Idina Menzel, Till Brönner, and Judith Hill.