In Hal Leonard’s 2005 book The Fifty Greatest Jazz Piano Players of All Time, Alexander was listed among the top five Jazz pianists of all time.
Alexander maintains a rigorous touring schedule worldwide, playing in jazz clubs, concert halls and playing at international Jazz Festivals in the USA and across continents; from Europe to Asia; in Montreux, Switzerland; Johannesburg and Cape Town, South Africa; and Japan, Russia, New Zealand, Australia, etc.
To date Monty Alexander has recorded over 70 albums as a leader. His collaboration with Telarc label yielded trio sessions (Impressions in Blue) and live concert recordings (Goin' Yard). In the late summer of 2005, Alexander traveled to Bob Marley's Tuff Gong Studio in Kingston, Jamaica, and teamed up with Jamaican top session players to record Concrete Jungle, a set of twelve compositions penned by Bob Marley and reinterpreted via Alexander's jazz piano-oriented arrangements. The resulting union of musical perspectives digs deep into the Marley legend and brings together the two worlds that Alexander most treasures, building the musical bridges that are the very essence of his craft.
As a testament to his versatility, The Good Life, on Chesky Records is a collection of songs written and popularized by one of his all-time favorite artists and good friends, Tony Bennett. His second release on Chesky, Calypso Blues, is tribute to another one of his heroes, Nat "King" Cole.
In 2008, with the invitation of Wynton Marsalis, Alexander conceived and directed the acclaimed program Lords of the West Indies at Jazz at Lincoln Center, broadcast nationally on BETJ. Alexander returned to Jazz at Lincoln Center in 2009 with a new program, Harlem Kingston Express in which he merged classic Jazz with rhythms and vibrations of his native Jamaica.
In the winter of 2008 American singer and icon, Tony Bennett personally invited Monty to record as the featured pianist on his Christmas album, A Swinging Christmas, with the Count Basie Orchestra. Monty can be spotted on the album cover, holding a turkey next to Tony Bennett.
Two collections were released in 2011 that capture the excitement of Monty Alexander's live performances around the world: Uplift, a trio album on JLP Records, and Harlem-Kingston Express on Motema Music.
Harlem Kinston Express: Live! was singled out by both the recording industry and fans and received a Grammy award nomination in 2012.
Between Uplift and Harlem-Kingston Express: Live! Monty Alexander has officially dominated the US radio charts with three number 1 spots in 2011, as not only Uplift remained at number 1 for several weeks but Harlem-Kingston Express: Live! rose to number 1 on Jazz charts and on World Music charts concurrently.
In the summer of 2012 Monty Alexander was awarded the prestigious German Jazz Trophy, “A Life for Jazz” and in November 2012 he received the Caribbean American Heritage Luminary Award from the Institute of Caribbean Studies in Washington, D.C.