He began his professional career as an on-stage backing vocalist for American entertainer Michael Jackson during his Bad world tour in 1987.
Holley has also worked for several years as an associate music director and vocal coach for the singing competition American Idol.
[2] Holley first performed with pop superstar Michael Jackson during the entertainer's first solo concert series, the Bad world tour.
Beginning in Japan in September 1987, the tour lasted for 16 months, during which time he visited 15 countries while serving as a backing singer for Jackson, along with Kevin Dorsey, Darryl Phinnessee and Sheryl Crow.
The two singers were part of an 11-man backing ensemble, when Stewart performed at the Pacific Amphitheatre in Costa Mesa, Orange County, and in California in September 1991.
The Los Angeles Times described in a review of the concert that the song was "embellished with a delicious a cappella doo-wop break featuring the 46-year-old star and backup singers Darryl Phinnessee and Dorian Holley".
[7] The two vocalists were also praised by the Chicago Tribune after a performance at the Poplar Creek Music Theatre, where their "sublime harmonies" "formed a perfect counterpoint to Stewart's impassioned pleas on 'This Old Heart of Mine'".
[9] Holley returned to work with Jackson for the Dangerous World Tour (June 1992–November 1993), a 69 date concert series which was attended by almost 3.5 million fans.
In 1994, he joined with Kate Markowitz, Valerie Carter, and David Lasley to form what The Pantagraph and The Boston Globe respectively described as a "wonderful" and "angelic" backing group to James Taylor.
[16] The St. Louis Post-Dispatch revealed during a performance of the same song at Riverport Amphitheater that the backing vocalist "sang a spirited solo that drew an ovation equal to anything Taylor had drawn thus far".
Holley worked with Michael Jackson again for the entertainer's last concert series, the HIStory World Tour, which began in Prague, Czech in September 1996.
"[12] He has also served for several years as an associate music director and vocal coach for the reality singing competition American Idol.
Holley added that it is common for some of the contestants to "crumble" upon leaving the stage if they have received critical comments from judge Simon Cowell.
He drew inspiration from his time on American Idol, as well as his experience with artists such as Stevie Wonder, Christina Aguilera, Kanye West and Queen Latifah.
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.
[28] The Standard noted in 2007 that the couple had purchased a 3,500-square-foot (330 m2) Italian Renaissance Revival home in Lafayette Square, Los Angeles.