From bookie to record mogul to big-screen gangster to Music Row exec, the strange but true life of Frank Dileo
by Jack Silverman
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.”
Funny How? Tuddy (Frank Dileo) gets ready to whack Tommy (Joe Pesci)
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.
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.”
Still, Dileo’s hot streak at Epic can hardly be pinned exclusively on his use of indies. Every major label at the time had a sizable budget for independent promotion—whether or not it was a shady business, the playing field was level. Yet in a short time, Epic had risen from No. 14 to No. 2, in no small part because of the way Dileo handled a record that would become the greatest-selling album of all time. That wasn’t lost on the man whose name is emblazoned, in script, in the upper left corner of its cover.
The Kingmaker Dileo and Jackson during their ’80s reign
In the wake of Michael Jackson’s free fall into scandal and talk-show punchlines, it’s easy to forget how he galvanized pop music almost exactly 25 years ago. When Jackson released Thriller in December 1982, in the heart of Frank Dileo’s Epic reign, it went on to sell more than 51 million copies. Though exact sales vary, these facts do not: The album was No. 1 on Billboard’s album chart for 37 weeks, it spawned seven Top 10 hits (tied for the record), and it helped bring Jackson an unprecedented eight statues at the 1984 Grammy Awards.
Jackson may look naive, but when it comes to business, he’s no chimp-cuddling moonbeam. In Hit Men, Walter Yetnikoff says of Jackson, “He has made observations to me about things like promotion which indicate he would be totally qualified to run a record label if he so desired.” Dannen himself describes Jackson as “an ambitious man with extensive knowledge of the record industry’s workings.”
In his 1988 autobiography Moon Walk, Jackson writes, “Frank was responsible for turning my dream for Thriller into a reality. His brilliant understanding of the recording industry proved invaluable. For instance, we released ‘Beat It’ as a single while ‘Billie Jean’ was still at No. 1. CBS screamed, ‘You’re crazy, this will kill “Billie Jean.” ’ But Frank told them not to worry, that both songs would be No. 1 and both would be in the Top 10 at the same time. They were.
Not to mention that Dileo convinced a recalcitrant Jackson to do the video for “Thriller,” a 14-minute film considered by some the best music video of all time. “Actually, he only wanted to do two videos—‘Billie Jean’ and ‘Beat It,’ ” Dileo says. “So while I was still working for Epic, [product manager] Larry Stessel asked me to fly out there and talk him into doing ‘Thriller,’ because he was pretty adamant that he wouldn’t do it.”
Jackson, who had been without a manager for eight months, asked Dileo to fill the position on a Monday in March 1984 at the Beverly Hills Hotel. Two days later, when Dileo accepted, the music industry was abuzz. One unnamed source in Dannen’s book says, “Everyone turned fucking green when Frank pulled that one off.”
Out of the record-label frying pan, into the megastar-management fire. Dileo started managing Jackson three months before the start of the Victory Tour, which reunited all of the Jackson brothers.
“Believe me, that was work,” Dileo says. “Every brother had a lawyer and an accountant. We had to have white promoters and black promoters. It was quite a complicated fiasco. But I got Michael through it safely.” Among the three black promoters: Don King and the Rev. Al Sharpton. “That was before Rev. Al Sharpton owned a suit. He was still in sweats,” Dileo recalls. Bill Bennett, head of Warner Nashville and a friend of Dileo’s since the late ’70s, has one particularly fond memory of the Victory Tour’s opening night. “We were in Kansas City,” Bennett says, “and I said, ‘Frank, I’m going to Arthur Bryant’s,’ which is one of the most famous homes of barbecue in the world. And Michael looked at me and said, ‘Oh no, Bill, Frank’s a vegetarian now.’ So Frank goes, ‘Yeah, Michael’s looking out for my health.’ As he walks me out the door, he gives me a key and says, ‘Meet me in this room when you get back, and bring some barbecue.’ ”
Heady Company Dileo with Jesse Jackson and Don King
“Michael used to moderate everything I ate,” Dileo says. “It’s amazing—when I started with him I was 210; when I ended with him, I was 265. So that’s what eating healthy does to you.”
After the Victory Tour, Jackson spent the next two years working on Bad. It sold a mere 32 million albums globally. Though it had fewer Top 10 hits than Thriller, it outdid its predecessor—and every other album in history—in another statistic: five No. 1 singles. In September 1987, Jackson embarked on his first tour as a solo performer, the Bad World Tour, which Dileo produced. Though the hassles of dealing with the Jackson brothers’ handlers were absent, Dileo was in for the ride of his life—123 dates over 16-and-a-half months. It was the largest-grossing tour of all time, putting Michael in front of 4.4 million fans on four continents.
“It was a headache,” Dileo says—a grand understatement to be sure. “You were moving 213 people every three days. In London, we played Wembley Stadium seven times in a row, 72,000 people a night. And we could have probably played it 10 or 12 nights, but at the time they only had seven available.”
Of course, there was a lot more to managing Michael Jackson than producing world tours. “We did a lot of things, Michael and I,” Dileo says fondly. “I got to executive produce all the videos of the Bad album. I did Moonwalker. I got nominated for two Grammys: for ‘Smooth Criminal’ and ‘Leave Me Alone.’ And I won a Grammy for ‘Leave Me Alone’—as the producer of the video, not the record.”
Another managerial coup from Dileo’s Jackson stint was his negotiation for the Pepsi commercial. “I got [Pepsi CEO] Roger Enrico to pay me up front, which was never done before,” he says. “In fact, we cut the deal on the Pepsi jet. Once we agreed upon a price, I said to Roger, ‘OK, there’s just one more thing. You’ve got to pay it all up front.’ He says, ‘I don’t know.’ And I said, ‘Roger, did Elvis Presley ever do a commercial for Pepsi?’ He said no. I said, ‘Did The Beatles?’ He said no. I said, ‘What do you want to be—0 for 3?’ He shook his head and went into the men’s room and came back and said, ‘OK, you got a deal.’ ” Dileo harbors no ill will toward Jackson over his firing in February 1989. “It’s a shame it ended,” Dileo says. “I really like Michael. It ended for a lot of reasons. First of all, Michael and I spent every day together for five-and-a-half years. A lot of people were jealous of that. And at that point in time, we had a lot of power between us. There was one or two record executives, and a lawyer, possibly two lawyers, that sort of needed me to get out of the way, so that they had more control with Michael. And it also was a way for them to get rid of Yetnikoff, who had a lot of power and was my friend.”
Dileo with an executive and Michael Jackson
It’s not hard to imagine why a bunch of industry suits wanted to get their hands on Jackson. But how was Jackson convinced? “Unfortunately, they talked Michael into it,” Dileo says, “by promising him—now this is according to Michael, and I believe this—by promising him that if he fired me and hired Sandy Gallin, that he’d be able to make movies in Hollywood. Now the truth be told, Michael never made a movie. The only movie [besides 1978’s The Wiz] he’s ever made was with me, and that was Moonwalker.”
ontrary to what you might expect, Frank Dileo’s Music Row office is a humble space in a nondescript building on Music Row. There’s no Mercedes or Rolls out front, just a dented 1992 Honda Accord. He’s not preoccupied with impressing anyone. In fact, he was hesitant to be the subject of a newspaper profile—“I just don’t want to come off as cocky,” he says. Several times, he mentions peers that he says he’d love to get into the story, to share the credit, and he makes a point to emphasize that he’d be lost without his assistant, Lauren Denig, whom he affectionately refers to as “Little Caesar.”
Wheelin’ and Dealin’ Dileo’s Music Row office
But hanging on those office walls are enough gold and platinum records to make your head spin, many of them multiples: Culture Club’s Colour by Numbers
, Cyndi Lauper’s She’s So Unusual
, The Clash’s Combat Rock
, and the crowning jewel: a case with 31 platinum copies of Thriller
. Not to mention singles by Electric Light Orchestra, Charley Pride, Billy Swan, Harry Nilsson and Elvis Presley.
But the real eye-poppers are the framed photographs. Seven Goodfellas
stills are arranged in one large frame that hangs over the couch. There are shots of Frank with Prince Charles, with Charlie Daniels, with Michael and the Reagans at the White House.
Immediately to the right of the door are four small photos that sum up the Frank Dileo story. Frank and his good friend, the late Col. Tom Parker. Frank and Martin Scorsese. Frank and—wait, is that him kissing Pope John Paul II’s ring? Believe it. A CBS executive in England wanted to thank Frank for his work on several records by overseas acts, including Nena’s “99 Luftballoons.” “He asked what he could do for me,” Frank recalls. “I said I want to meet the pope. Believe it or not, as wild of a life as I’ve led, I don’t miss church on Sunday.”
Who’s the Guy in the Hat? Dileo gets (gives?) some sage advice.
The fourth shot is of Frank and Michael Jackson, from behind, standing at urinals in a public restroom. Above Michael’s head, in Michael’s handwriting, are the words, “This water sure is cold.” Above Frank’s head, he wrote, “It’s deep too.”
When Jackson went on trial in 2005, Frank stayed in Los Angeles for over three months, on his own dime. “I know that he is innocent,” Dileo says. “A lot of people attack him for a lot of different reasons. One is, everybody would love to get their hands on the Beatles’ publishing. And he’s just one of those guys, he’s real kind and real nice and he can easily be taken advantage of.
“In this particular case, this kid had cancer, he found him a doctor, they didn’t have any money, he allowed them to live on his ranch. And when it was over, they didn’t want to leave. It was like blackmail. That’s all it was.
“We talked at each and every break,” Dileo continues. “I wanted to let him know that I know he didn’t do it. In fact, when I went there, he didn’t know I was coming. It was very emotional. He went, ‘Frank, I can’t believe you’re here.’ And he started to cry. And I went over and I hugged him and we got on the elevator and he told [defense attorney] Tom Mesereau, ‘This is Frank Dileo. He used to manage me. I’ve had nine managers since then. He’s the only guy that showed up, or even called to see how I’m doing.’ That was a very rough thing on him, a very emotional thing.”
The years since the whirlwind 1980s have been a little less action-packed. In the ’90s, Frank opened a New York office and managed or co-managed several acts, including Taylor Dayne, Jodeci and Laura Branigan. And he got into the restaurant business, partnering with Robert De Niro on New York City’s famed Tribeca Grill.
“I was the first guy up with the money,” he says. “Outside of Bobby and Drew [the manager], there was me.” Several other investors had smaller shares, among them Christopher Walken, Lou Diamond Phillips, Sean Penn, Bill Murray and Ed Harris. Dileo sold his share after more than 11 years, splitting his portion three ways among the restaurant’s three oldest employees.
Since the mid-’90s, Dileo’s been keeping a low profile. He’s a family man—he’s been married to his wife Linda for 31 years, and wanted to be near his son and daughter, both of whom were attending the George School. So he moved for a while to Bucks County, outside Philadelphia. After his daughter graduated, nearly eight years later, he moved back to Ohio.
Shortly thereafter, Dileo started to lose his eyesight. By 2004, he was blind, a result of diabetic retinopathy. But a series of four operations over the next couple of years restored much of his sight. Since coming to Music City in January, Dileo had attempted to help get the failing nightclub 12th & Porter out of dire straits. But that endeavor fell through last week.
“It’s been in Chapter 11,” Dileo says. “I’ve been trying to save it for the writing community, because it does have the best sound. But unfortunately, with the past debt, the leases that have been incurred and the obscure management style, there’s just no way to overcome the debt to make it work. So I have to pull out of it and let nature take its course.”
Meanwhile, he’s started a management company, where he’s working with singer-songwriter Galen Griffin. And he’s about to pen a deal to start a publishing company with a successful songwriter/producer. He doesn’t want to name names until the i’s are dotted and the t’s are crossed.
So after so much success, why keep going? “I’m in it for the love of it,” Dileo says. “I mean, hey, I want to make some money for my kids. I’d like to make it more comfortable for them and my grandson, who’s 3 years old now. And I really love the music, I love the business, I love the artists. That’s why I’m here.”
Perhaps Frank Dileo was just born to be a mover and shaker, a notion that McGee Management’s Frank Rand confirms. “I was an A&R guy before [Frank] started working for Michael,” Rand says. “And A&R people and promotion people are always butting heads—they can never get us enough airplay and we can never give them enough hits. So one day I went in to Frank’s office and we started talking, and we had a constructive argument. I don’t even know what brought it up, but I said, ‘Frank, we’re in the record business!’ “And Frank said, ‘Hold on right there! You’re
in the record business. I’m in show