DiLeo, an Italian American, is a native of East Liberty, Pittsburgh, Pennsylvania. He began his career in the music industry in the late 1960s, shortly after high school, as a rack jobber (distributing records to retail stores) in Pittsburgh. Following a number of brief, higher-profile jobs, he was hired as a promotion staffer in Cleveland by CBS Records subsidiary Epic Records in 1968. He promoted albums by The Hollies, Donovan and Sly & the Family Stone to local radio stations, and was later promoted to the company’s regional office in Chicago. Circa 1969 he was “headhunted” by RCA Records in New York, followed by a stint at Bell Records. After a year with Bell he “retired” from the music business and moved back to Pittsburgh. His return to the music industry was prompted by an “electrical fire” which destroyed his Pittsburgh home, for which his insurance carrier reportedly refused to pay out.
Frederic Dannen described DiLeo as an “outspoken fan” of the controversial record industry practice of using “Indies” (independent record promoters) to promote new singles to radio stations, a system which was widely described as “the new payola” and which by the early 1980s was reportedly costing the major US record labels tens of millions of dollars per year. DiLeo was also a close friend of Hollywood-based record promoter Joe Isgro, one of the leading figures in the shadowy indie group dubbed “The Network”, who was alleged to have close ties with the Gambino crime family.
In 1979, CBS Records president Walter Yetnikoff hired his old friend DiLeo to work for Epic Records in New York as Vice President of National Promotion. Overseeing a staff of 65 people and a multi-million dollar budget, Frank helped guide Epic Records from a small $65 million dollar company to a $250 million dollar powerhouse; during this period Epic outperformed its sister label Columbia Records for two years running. Artists signed to Epic included Quiet Riot, REO Speedwagon, Ozzy Osbourne, Gloria Estefan, Luther Vandross, Meat Loaf, Cyndi Lauper, Culture Club and Michael Jackson, among others. He was voted executive of the year for Epic Records, received over 80 gold and platinum awards, and was credited for taking Epic Records from the number fourteen label in the U.S. market to number two.
In 1984, after the record-setting success of his Thriller album, Michael Jackson asked DiLeo to take over as his manager. DiLeo was the executive producer for the full-length movie Moonwalker, wrote and executive produced three Pepsi-Cola commercials (including negotiating a landmark endorsement deal), and eight music videos including the Grammy winning video “Leave Me Alone”. DiLeo managed Jackson’s Bad World Tour, and the Jackson family’s Victory Tour. DiLeo managed Jackson until February 14, 1989 when their business relationship was abruptly terminated, without any public explanation.
In 2009, The Wall Street Journal reported that DiLeo was once again managing Michael Jackson’s career.
DiLeo also managed the careers of Taylor Dayne, Jodeci, Laura Branigan, and Bon Jovi guitarist Richie Sambora, and has worked with Prince on several projects.
Today DiLeo has founded Dileo Entertainment Group, a company located in Nashville, Tennessee. The company is focused on managing up and coming artists as well as establishing a publishing company in Nashville. DiLeo has appeared in three major motion pictures. His film credits include GoodFellas, Wayne’s World and Wayne’s World 2.