Holley's last experiences with Jackson were in 2009, when he prepared for a scheduled 50-date concert series called This Is It. Holley rehearsed with Jackson as a backing singer at the Staples Center in Los Angeles and was also hired as the vocal director for the ill-fated shows. He was present on the singer's last night of rehearsals in June 2009. Hours later, Jackson died after he entered into cardiac arrest at his nearby home. Holley sang during the group rendition of We Are the World at the entertainer's memorial service the subsequent month. He was joined by fellow "This Is It" backing vocalists Darryl Phinnessee, Judith Hill and Orianthi.