DownBeat Double Blindfold Test: Tim Jackson vs. Gerald Clayton

The DownBeat “Blindfold Test” is a listening test that challenges the featured artist to discuss and identify the music and musicians who performed on selected recordings. The artist is then asked to rate each tune using a 5-star system. No information is given to the artist prior to the test.
Tim Jackson was the Artistic Director of the Monterey Jazz Festival (MJF) from 1992-2023 and co-founded Kuumbwa Jazz in Santa Cruz in 1975. A lifelong jazz and nonprofit professional, Jackson’s leadership in West Coast music presentation has been recognized with awards from the California Arts Council, Arts Council for Monterey County, California Jazz Foundation, Santa Cruz County Arts Commission, Jazz Journalists Association, and the Recording Academy. In 2016, he received Berklee College of Music’s George Wein Impresario Award and DownBeat magazine’s Lifetime Achievement Award in 2023. Most recently, Jazz at Lincoln Center presented Jackson with their 2024 Ed Bradley Award for Leadership in Jazz.
The festival’s musical spectrum and educational programs were revitalized and expanded under Jackson’s tenure, with new opportunities for jazz artists and audience development through six national tours and a record label for MJF’s archival performances. Jackson also reinstated MJF’s artist-in-residence and commission programs—seven of the festival’s 32 original works have been commercially recorded and three have received GRAMMY Awards or nominations.
Jackson is a founding member of the Western Jazz Presenters Network (WJPN) and brought MJF to the International Jazz Festivals Organization (IJFO) as the first non-European member. He has served on advisory panels for the Mid-Atlantic Arts Foundation, National Endowment for the Arts, California Arts Council, Jazz Congress, and the Doris Duke Charitable Foundation.
Seven-time GRAMMY nominated pianist-composer and Blue Note Artist Gerald Clayton searches for honest expression in every note. An alumnus of Los Angeles County High School for the Arts, USC’s Thornton School of Music and the Manhattan School of Music, Clayton won second place in the Monk Institute of Jazz Piano Competition in 2006. For the following decade, he toured globally both as a band leader and special guest sideman to critical and commercial acclaim.
In 2016, Duke University commissioned Clayton’s evening-length composition “Piedmont Blues” which featured a mixed media performance of critical acclaim. Clayton received a commission from Los Angeles County Museum of Art in 2019 to compose a musical pendant for artist Charles White’s “5 Great American Negroes” mural spotlighting race and racial tensions with the project White Cities: A Musical Tribute to Charles White. In 2020, Clayton scored Sam Pollard’s award-winning documentary film MLK/FBI.
Throughout his career, Clayton has also collaborated with such distinctive artists as Bill Frisell, Roy Hargrove, Dianne Reeves, John Scofield, and legendary band leader Charles Lloyd among many others. He currently serves as Director of Monterey Jazz Festival’s Next Generation Jazz Orchestra and has served as Musical Director for Monterey Jazz Festival on Tour and the more recent Blue Note 85th Anniversary Tour. In April 2025, Blue Note records released Ones & Twos, Clayton’s highly-anticipated album featuring Elena Pinderhughes, Joel Ross, Marquis Hill, Kendrick Scott and Kassa Overall.