Hit Man

Frank Dileo was at his home in eastern Ohio, just outside of Pittsburgh, when he got the phone call that would have him blowing Joe Pesci’s Technicolor brains all over the big screen. It had been just two days earlier that he’d received another, far less heartening call. With the punch of a few buttons, he’d been sacked from the most coveted job in the music industry, a job he’d held for five years—that of Michael Jackson’s manager.

It was late winter 1989, and Dileo and Jackson had just finished the grueling 16-month-long Bad World Tour. The stress of moving the MJ circus—213 strong—every three days across four continents had caused Dileo to put on considerable weight. So he headed to Duke University’s medical center to trim down and regain his health. Good thing, too, because doctors discovered he’d developed diabetes. A week into his weight-loss regimen, he got the news that he’d been unceremoniously dumped by the King of Pop.

Dangerously overweight. Diabetic. Fired by Michael Jackson. Not what you would call an auspicious turn of events. But if you ever see Frank Dileo pick up the dice at a craps table, put all your chips on the pass line—because if history’s any indicator, he’ll roll a 7 or 11. Screw the law of averages. His hot streaks make the Harlem Globetrotters look like Charlie Brown with a football.

But that didn’t stop the vultures from circling the Duke campus once the Jackson news dropped. To escape the media frenzy, Dileo headed for the refuge of his Ohio home. The following day, Frank recalls, people were calling his house to see what happened. It didn’t sound like any big deal when his wife said, “Hey, Martin Scorsese’s on the phone.”

Three years earlier, Scorsese had directed Jackson’s “Bad” video. Offhandedly, he told Dileo, the video’s executive producer, that he looked like a character in the director’s next picture. Wiseguys, it was called, based on a true-crime book about a mobster who flipped on his cronies. Dileo wrote it off as banter. Now here the guy was, years later, calling out of the blue.

“I thought, OK, he probably wants to say, gee, sorry to hear what happened,” Dileo says. “So I say, ‘Hey Marty, how you doin’?’ He said, [impersonating Scorsese’s clenched delivery] ‘Hey, you remember three years ago, I talked to you about doing a movie?’ I said, ‘Yeah, the book Wiseguy.’ He said, ‘Well, I’m casting today. Will you still do it?’ And I said, ‘Yeah. I thought you were calling because I got fired.’

“And he says, ‘Oh, did you get fired?’ He didn’t know.”

Just like that, a guy with neither acting experience nor aspirations winds up working for perhaps the greatest director of his generation in one of the best movies of the decade, Goodfellas. Not to mention he gets to turn Pesci’s gray matter red in one of cinema’s most storied whack jobs. All this, just two days after being fired by the biggest act in the business.

For anyone else, this would all be highly improbable. But for Frank Dileo, it’s par for the course. His life story has more highlights than Farrah Fawcett’s hair and reads better than half the screenplays floating around Hollywood. And in January, it brought him back to Nashville—where he lived briefly in the early ’70s—to get back into what he insistently calls “show business.” He already opened a management company and is getting ready to open a publishing company.

But let’s not get ahead of ourselves. As Frank Dileo knows better than anyone, timing is everything.

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.