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About five years ago, a dear friend of mine introduced me to Amy Winehouse's music with a grim prophecy: "You should check out her stuff. And she's probably going to die soon."

Three seconds into "Me and Mr. Jones," I was hooked. It didn't really matter that I couldn't quite comprehend all her words, slurred and bent with a thick English accent.

It was the voice that got me - soaring from the speakers, big and bold and bobbing around the pitch, leaving even the most mundane lyrics swollen with meaning.

But music was never the problem for Amy Winehouse, who was found dead in her London apartment on Saturday at age 27. Long before her song "Rehab" became part of the international vernacular, Winehouse struggled mightily with a slew of addictions ranging from alcohol to crack cocaine.

She often arrived at shows so intoxicated that she couldn't remember the words to her own songs; she was booed off the stage in Belgrade this year in what turned out to be one of her final gigs.

The musical world lost one of its greatest talents this weekend, and though the human toll must be considered first, the economics of Winehouse and her music are staggering.

Her 2006 smash album, Back To Black, sold roughly 10 million copies worldwide; FORBES estimates that Winehouse earned $40 million before taxes and agent/manager fees in the five years since. Her erratic live appearances were in high demand, and Winehouse occasionally received one million pound checks for playing private gigs for the likes of Russian billionaire Roman Abramovich.

"She was on her way to becoming a major headliner, much like Katy Perry and Adele, and much the way Lady Gaga is today," says Randy Phillips, chief of concert promoter AEG. "Her music really cut through the clutter. It was very unique, very different."

Phillips estimates that Winehouse commanded a guarantee in the neighborhood of $250,000 per night when her popularity was at its peak in 2007-2008, and double that for lucrative festival performances. That would have placed her above most other touring acts and just short of the rarified air of Beyonce and Lady Gaga, two artists who regularly gross seven figures per night.

Had Winehouse lived and pulled herself together, there's no reason to believe she couldn't have recorded many more successful albums and made scads of money on the road. According to concert data provider Pollstar, Winehouse topped $1 million per night in gross ticket sales during five dates this winter in Brazil.

"South America was very successful earlier this year," says Pollstar editor Gary Bongiovanni. "She certainly would not average a $1.8 million gross in the states."

Winehouse got in her own way too often to earn that kind of money on a regular basis, showing up at concerts too drunk to perform and canceling dozens of shows due to unspecified health concerns. She didn't make many friends along the way, reportedly telling U2 frontman Bono "Shut up! I don't give a f*ck!" at an award ceremony. When asked about her record label, she once said, "I hate them f*ckers, man … they know they're idiots … I have no respect for them whatsoever."

Despite Winehouse's well-documented personal struggles, industry insiders say she was no fool when it came to her business. In 2009 she even started her own label, Lioness Records, which grew to hold a roster of three performers - including Winehouse's 13-year-old goddaughter, Dionne Bromfield, who has since released two albums.

"[Winehouse] had a relatively practical sense about managing her business," says Lori Landew, an entertainment attorney at Fox Rothschild in Philadelphia. "There was a general sense that even with her apparent issues and trouble, she was very smart and very capable in certain areas of her life … other areas, not so much."

Winehouse was a throwback in many ways, from her soul-infused sound to her self-destructive habits. Fortunately for the music world, many artists now exhibit plenty of business savvy without the self-destructive tendencies - take Jay-Z, Beyonce and Lady Gaga - and one could argue that the entertainer-as-entrepreneur template has replaced that of the troubled artist, making Winehouse's death all the more jarring.

As for Winehouse's legacy, there are reports that a posthumous album is already in the works. It seems demand for such an offering would be high, as Back To Black shot up to the top of Britain's iTunes charts immediately after her death.

Given these strong sales and heavy radio play, along with the fact that Winehouse likely hadn't yet received an advance for her new album, it's probable she'll earn in excess of seven figures this year from beyond the grave.

It's hard to tell how much she left behind, or who's slated to inherit it. But there's no doubt that death can do wonders for a musician's earnings prospects - just look at Michael Jackson, whose estate has taken in $400 million in the two years since his passing.