On Friday, August 18, onetime boy-band impresario and lifelong con-man Lou Pearlman — imprisoned in a federal penitentiary since 2008 — died at the age of 62 of cardiac arrest at a Miami hospital where he was scheduled to have heart surgery. Those who knew him best were pretty much satisfied with that ending.
In the late 1990s and early 2000s, however, Pearlman was celebrated, admired and even adored, an affable King Midas of pop with a magnetic personality. He was a walking exercise in irony: The middle-aged, nasal-voiced, balding and 300-plus-pound Queens, New York, native surrounded himself with chiseled, underage singers and dancers.
He didn’t invent boy bands, but the ones he formed dominated charts, shattered sales records and helped propel Clive Calder’s Jive Records toward a $2.74 billion buyout by BMG in 2003, the largest ever at the time. Pearlman started Backstreet Boys, whose third studio album Millennium reached No. 1 on the Billboard 200 in 1999 and became the biggest-selling album of the year; to date, Backstreet Boys have sold 31.5 million albums in the U.S. Next he created *NSYNC, whose 2.42 million single-week sales of their 2000 album No Strings Attached set a record that lasted until Adele broke it in 2015. Pearlman played a seminal role in the careers of Justin Timberlake, Lance Bass, Joey Fatone and many others. He followed his two biggest acts with a long tail of less-successful others: O-Town, LFO, Take 5, Natural and Aaron Carter, to name a few.
Many who did business with Pearlman, though, remember him as a financial criminal. In 2008, he was convicted of two counts of conspiracy, one count of money laundering and one count of making false statements during a bankruptcy proceeding. He was sentenced to 300 months in prison, one for every million investigators said he stole in a massive Ponzi scheme involving fake savings accounts and a fake airline business.
Still others, including Nick, Aaron and Jane Carter, Denise McLean (mother of Backstreet Boy A.J.), Pearlman’s former drivers, and young entertainers such as Tim Christofore of Take 5 have charged throughout the years that Pearlman acted in physically inappropriate ways with boys he groomed for success. Echoes of his alleged casting-couch exploits still reverberate through today’s pop music world. In recent years, several prominent figures have made public accusations about entertainment industry luminaries who reportedly victimized aspiring artists. Kesha has claimed sexual assault at the hands of her producer, Dr. Luke; Metropolitan Police in the U.K. documented hundreds of sexual abuse incidents involving English television and radio personality Jimmy Savile.
“Lou Pearlman is one of the most iconic figures in popular music and culture,” says Songwriters Hall of Fame inductee Desmond Child, who collaborated on hits with everyone from Aerosmith and Bon Jovi to Ricky Martin and Zedd. He, John Stamos and Andreas Carlsson (a collaborator on *NSYNC’s hits “Bye, Bye, Bye” and Backstreet’s “I Want It That Way”) are currently in development on a movie about Pearlman. “His unseen influence has dominated the airwaves, from the first Backstreet Boys single to every inescapable smash by One Direction, Justin Bieber and Nick Jonas.”
If the man once known as “Big Poppa” to his beloved boys had his way, the story of his legacy would begin and end with his pop music success and influence. But his later life was dominated by desperation to prove he was worthy of the credit he gave himself.
When I interviewed him in an Orange County, Florida, jail in July 2007, Pearlman was facing decades in prison for charges related to his $300 million Ponzi scheme; the money had helped him start his bands. Nevertheless, he was upbeat and eager to celebrate all the joy he said he’s brought into people’s lives. “I’m planning on this chapter ending relatively soon,” he told me. As recently as 2014, Pearlman told The Hollywood Reporter, “I’ll be back.”
He was due to get out in 2029, but he wasn’t sitting idle. He hosted visitors, opportunists who wanted to believe in his comeback, or financial victims eager to empower him with a way to recoup their investments.
“He was able to make people think they were the most important people in the world, but he didn’t have it in him to connect deeply,” says Tammie Hilton. She was Pearlman’s Florence Nightingale, a nurse who took care of him in 1996 when a cyst on his liver ruptured and almost cost his life. Known by some as Pearlman’s girlfriend for a time, she remained the closest to him for longest, even though Hilton said she quit believing anything he said a long time ago. Others were still enamored. “He had anybody that he could putting money in his commissary account,” Hilton says.
“No matter what he did, he never had the ability to be honest,” says Alan Gross, Pearlman’s closest childhood friend. Gross still lives in the Flushing apartment across from the former airfield where the two used to watch blimps come and go; the Pearlmans lived a floor beneath him. Lou was the only child of Reenie and Hy Pearlman, who owned a dry cleaning business. Lou became known around the building for his relation to Art Garfunkel, his cousin; the first time Gross saw Garfunkel perform was at a family dinner with Lou. Gross encouraged Pearlman’s interest in blimps and helped set him up in his first blimp business but pulled away as Pearlman became more desperate for fortune and fame. “He really changed my life,” Gross says. “I would have been a pretty boring person without him. But if it wasn’t for me, he wouldn’t have gotten his start in the first place.”
For his first real blimp company, Pearlman convinced the brothers behind Jordache jeans to come on as a sponsor. He emblazoned a patchwork airship with heavy gold paint and the Jordache logo. It was supposed to fly into Manhattan, but on its maiden voyage from Lakehurst, New Jersey, the craft took off, went into a spiral and crashed in a nearby garbage dump. Pearlman parlayed the insurance money into an airship company that eventually went public (thanks to a dodgy penny-stock scheme). Still, almost every one of his blimps eventually crashed.
By the early 2000s, though, he had enough of a profile to lure investors in his Trans Continental Airlines, which supposedly operated more than 49 planes. In fact, he owned none. Even the company’s brochure was a lie. It depicted one of Pearlman’s jets talking off, but the jet in the photo was actually a toy. Pearlman’s fingers were holding the tail and barely cropped out of the shot.
A constant flow of investment money allowed Pearlman to hold an open casting call near Disney in Orlando, choose his talent, then sink millions into developing and promoting his boy bands, first in Europe, then in the U.S. He spent plenty cultivating his own outsized image, too, seizing a share of the spotlight rarely reserved for even the most flamboyant pop producers. He tooled around in a cornflower-blue Rolls-Royce. He had a life-size statue of Anakin Skywalker and an Uzi submachine gun, part of a weird collection of grown-up toys later auctioned off in an attempt to reclaim funds for his bilked investors. In the end, they got just about 5 cents on the dollar. “The likelihood of there being a golden pot somewhere is remote,” bankruptcy trustee Soneet Kapila told me in July 2015.
In 1997, Pearlman’s work shifted from maintaining his opulent image to grasping for redemption after Brian Littrell sued him on behalf of the Backstreet Boys. The band had vigorously toured, performed and promoted themselves at Pearlman’s urging from 1993 to 1997 but were told they’d earned just about $12,000 apiece. Pearlman had nickel-and-dimed them for every recoupable penny. Plus, he’d double-dipped by paying himself not only as a manager but as a sixth member of the band. *NSYNC followed the Backstreet suit. Timberlake famously said he’d been “financially raped by a Svengali.”
In fact, nearly every band that Pearlman ever launched sued him. Some acts accused him of inappropriate sexual behavior, including those who lived with him at his $12 million Orlando-area mansion. The harshest accusations came in a November 2007 Vanity Fair story by Bryan Burrough, “Mad About the Boys.” Pearlman denied the accusations and no charges were ever filed.
In the end, what did Pearlman in wasn’t the lawsuits; they were always settled privately. It was his bogus “Employee Investment Savings Accounts.” The accounts, which he said outperformed the market, were supposedly a benefit for those who worked for his Trans Continental empire, the catch-all for many of his almost 50 companies spanning entertainment, fashion modeling, airlines, restaurants and more. He invited investors to join the plan, which he promised was backed by the FDIC, AIG and Lloyd’s of London. It wasn’t. He’d forged insurance documents and financials just like he’d dreamed up an entire airline fleet.
Not even a day in court could keep Pearlman from scheming. At his sentencing, for conspiracy, money laundering and more, he asked federal judge G. Kendall Sharp to let him use the phone and Internet two days a week — so he could continue to manage his band US5 and earn back the money he’d bilked. The judge balked.
In the last eight years, Hilton has kept in somewhat regular contact with Pearlman via the prison’s messaging system. Most of the notes he wrote her were brief. They began with “Hey babe” and often promised he was getting out soon, even though Hilton knew better. “He never gave up. I don’t think he ever grasped his reality.”
After Pearlman suffered a stroke while in prison in 2010 (which gave him a temporary speech impediment and paralysis on one side of his body), he promised her he was getting in shape and losing weight. “Then I’d see a picture of him and he’d gained 15 pounds,” Hilton says.
Death, Hilton says, is the one thing that rattled Pearlman’s optimism. She met him on his deathbed (or so he believed) with a kidney problem. “He cried,” Hilton recalls. “He didn’t want to talk about it. It was always, ‘I can’t die. I have things to do.’” The last time she talked to him on the phone was just after his stroke in 2010. “He was afraid,” she says, “but he flipped and turned right into, ‘I’m not going to die.’ If he died he would never get to pay anyone back, he would never get to be bigger than he was.”
Hilton, like most of the famous and regular people who’ve commented on his death, have mixed feelings about his passing. Orlando lawyer Clay Townsend, who sued Pearlman a bunch of times on behalf of his various artists, including the Backstreet Boys, says via email that Pearlman’s death is “pretty emotional for some of us who wrestled with him for a decade for various victims. He was a one of a kind. Even in battle he was always pleasant to me (odd).”
While the artists Pearlman ripped off still credit him with discovering them, less fortunate are the investors whose life savings he stole, who saw their last hope of financial recovery die with him. “To say that Lou Pearlman was the most selfish person in the world is harsh,” Hilton says, “but it’s true.”
Tyler Gray is the author of the book The Hit Charade: Lou Pearlman, Boy Bands, and the Biggest Ponzi Scheme in U.S. History.