Pearlman With ‘N Sync

Pearlman, with (from left) 'N Sync's Chris Kirkpatrick, JC Chasez, Lance Bass, Joey Fatone and Justin Timberlake at N.Y.P.D. Pizza, one of Pearlman's 84 businesses.

A Drive for More Boy Bands

Pearlman with 'N Sync's Fatone (center) and Chasez circa 1996 at Miami's N.Y.P.D. Pizza. Five days before his May 2008 sentencing, Pearlman issued a formal request to be permitted to develop bands while behind bars; all he would require was a telephone and an Internet connection two days a week. Prosecutors objected strongly, as did Judge G. Kendall Sharp, who instead ordered Pearlman to 300 months in jail — one month per $1 million he admitted to stealing — with the stipulation that his sentence could be reduced one month per $1 million he repaid.

With Jonathan Lopez

Pearlman with Jonathan Lopez of C-Note, a Latin boy band.

Pearl Steakhouse

Pearl Steakhouse was among his many businesses. Pearlman says he "walks the track, Monday through Friday, if the weather is nice. I'm also taking a blood thinner, which helps me with my stroke situation." Pearlman suffered a stroke in 2010; prison staff got him to a hospital in time to save his life. He claims to have lost 75 pounds from walking, down to 250 after maxing out at 325. 

Lances Bass on Pearlman

"We didn't understand how he made his money. he had this company, that company — now he owns the Goodyear blimp. You blindly trusted him because you saw that he was well off, with tons of employees around him — it made it very legit. I believed him."

A.J. McLean on Pearlman

"Brian [Littrell] and I started singing Justin [Timberlake]'s "What Goes Around … Comes Around." You can't run from these things forever. You know if you're doing something bad from the very get-go, it's going to come back around and bite you in the ass," says the Backstreet Boy

Timberlake on Pearlman: I Was ‘Monetarily Raped’

"Looking back at those days … I was being monetarily raped by Svengali," the six-time Grammy winner says of living on a $35-a-day per diem while Pearlman reaped millions in revenue from 'N Sync.

Club Paris

Pearlman was flanked by businessman Fred Khalilian and Nicky Hilton at the opening of Club Paris. Behind bars, Pearlman generally gets along with fellow prisoners, a majority of whom he characterizes as white-collar criminals and corrupt public officials. He says the inmates with whom he has the best rapport are "the intelligent ones," while he makes sure to keep his distance from "drug dealers and crazies."

Home Sweet Homes

Above: The Federal Correctional Institution Texarkana, a low-security men's prison located 170 miles east of the Dallas-Fort Worth area, where Pearlman is imprisoned.

Below: Pearlman's former 16,000-square-foot, $12 million Italianate manse in Orlando. At its center was a huge teen-boy-friendly arcade.

Private Jet

Pearlman, who began flying by private jet in 1989, pictured in the Gulfstream with members of the boy band Natural.

Frequent Flyer

The boy band mogul was photographed en route to Atlanta via his private plane in 2003. 

Day in Court

Pearlman, photographed in 2007 at an Orlando court, where he faced multiple fraud charges. Despite nearly six years behind bars, Pearlman insists he is doing fine. "I'm feeling good. I'm OK," he says. With 15 years left, he clings to his boy-band dreams to keep sane, along with the promise of finding the next 14-year-old Justin Timberlake outside the walls of FCI Texarkana.

Pearlman and Nick Lachey

Pearlman posed with Nick Lachey of 98 Degrees (not one of the bands managed by Pearlman's Trans Continental) at a 2004 benefit.

‘Could Have Had It All’

Pearlman with a chimpanzee at an Orlando premiere. "The sad thing is, Lou could have had it all," says Lance Bass. "He could have had the new Motown in Orlando. But that's where greed comes in. He was just a really greedy person."

‘He Wanted to Touch My Dick’

"Lou spelled it out one day. He lost his temper on the phone and told me what he wanted: He told me he wanted to touch my dick."  Rich Cronin, the late LFO singer, in a revealing 2009 interview with Howard Stern about Pearlman's penchant for sexual harassment. Cronin died of leukemia in 2010 at age 36.

Gold Album

Gold Album