Dileo was the subject of a November 2007 Scene cover piece outlining his storied career. And we mean storied. He worked his way up from the bottom of the music industry to become one of the most powerful men in the biz. During his tenure at Epic Records, he was instrumental in signing or developing the careers of Culture Club, Cyndi Lauper, REO Speedwagon, Quiet Riot, The Clash and of course Jackson. Dileo lived in Nashville briefly in the ’70s and then moved here in January 2007 to start a management business, though he spent much of the last three years in Los Angeles after returning as Jackson's manager, and then handling issues with the late pop singer's estate.
His larger-than-life persona landed him a couple of movie roles, most famously as Tuddy Cicero in Martin Scorsese's Goodfellas. Not only did he play the brother to Mafia boss Paulie Cicero, but he was responsible for one of the most legendary mob hits in cinema history, putting a bullet in the back of Joe Pesci's head in the film's climactic scene.
An excerpt from the Scene story, about Dileo's ever-present cigar:
There’s speculation that when he emerged from the womb, 60 years ago last month, Frank Dileo already had a cigar in his mouth. Look at the pictures on his office walls and in his photo albums, and more often than not he’s either holding or chomping on a fat, unlit stogie.
As a mystique-building accessory, those cigars have long since earned their keep. On the wall of Dileo’s Music Row apartment hangs a framed cartoon by the renowned late cartoonist for the London Evening Standard, Raymond Allen Jackson (known as Jak). An enormous lit cigar, so big that four men are holding it, is coming through the front doors of the Mayfair Hotel. The smoker is not yet visible. The caption reads, “I don’t know about Michael Jackson—but here comes his manager.”
Add to the cigar his gold watch, pinkie ring, manicured hands and Music Row-casual attire, and Dileo could be the poster boy for National Dress the Part Week. At 5-foot-2, he looks like he stepped out of Central Casting’s Music Biz Dealmaker file. And whether or not such visual signifiers are essential to success in the music industry, Dileo’s track record—by 21 he was RCA’s national singles director, by 35 one of the most powerful men in the business—proves they certainly don’t hurt.