Industry FAIL: Four Musical Mistakes Of The Decade : Monitor Mix Schadenfreude never seems so sweet as when it's directed at the music industry. Here are a few of the top music business failures of the '00s.

Industry FAIL: Four Musical Mistakes Of The Decade

Spectacular flop #3: Kevin Federline. Mark Davis/Getty Images hide caption

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Mark Davis/Getty Images

Spectacular flop #3: Kevin Federline.

Mark Davis/Getty Images

Schadenfreude never seems as sweet as it does when it's directed at the music industry. We fans understand, of course, that the vast majority of those employed by said industry are passionate about what they do. Which makes it all the more fun to see the boneheads among us flounder in the public embarrassment of their worst decisions.

The chief failure of the recording industry this decade, some have written, was its initial decision to treat digital music as an enemy. Rather than find a way to embrace Napster and its 26 million users, the Recording Industry Association of America took legal action against the company, thus only diffusing and intensifying the methods and rate of piracy. With the genie freed from the bottle, the music business is still reeling.

In the shadow of said genie, many attempts have been made to stuff him back in or deal with his power. Some have changed the way we listen, while others have changed employment situations at record labels. With apologies to Perez Hilton Presents, Carly Hennessey (who?) and dropping the ball on Yankee Hotel Foxtrot, here are four of the top music-industry FAILs of the '00s. Please send us more in the comments below.

1. The Sony BMG Rootkit CDs

The copy-prevention software of Sony BMG, now just Sony Music Entertainment, was eventually classified as spyware by Microsoft. courtesy of Sony hide caption

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courtesy of Sony

Limiting the usage of music files with Digital Rights Management proved to be a FAIL at large for the industry — iTunes, for one, is entirely free of protected music now. But the most infamous of these failures was the copy protection based on "rootkit" technology on more than 100 CD releases. A rootkit is a software program which messes with the basic code in your computer's operating system, thus allowing viruses or spyware to infect your computer undetected. So not only was Sony's bid at DRM short-sighted, but it was also opening up security vulnerabilities in computers worldwide. (And it was hypocritical: Sony's rootkit developers illegally stole code from the LAME MP3-encoding technology.) When programmers discovered this, it led to several class-action lawsuits, not to mention the exact wrong kind of public attention.

2. RIAA Witch-Hunts

The punitive measures enacted by the RIAA were not only ineffective in stemming the illegal downloading tide, but they earned the ill will of many consumers. coreythrace / Flickr hide caption

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coreythrace / Flickr

The RIAA, which represents record companies, has been justly concerned this decade with the threat of piracy posed by online file-sharing. So, starting in 2003, it began a strategy of... arbitrarily suing people. More than 30,000 people so far have been threatened or pursued with legal action, often resulting in monetary settlements which far exceed the crime, while file-sharing continues unabated. While the RIAA has won some of its cases, it's certainly lost the public relations struggle. It sued a single mother earning $36,000 a year for nearly $2 million, after she allegedly shared 24 songs. It went after a 66-year-old sculptor for supposedly sharing gangsta rap on the Windows-based Kazaa program, even though she uses a Mac. It filed suit against an 83-year-old dead grandmother. Though it remains unclear whether you catch more digital-music customers with honey than vinegar, if the RIAA set out to capture any goodwill from the American consumer, it certainly got the exact opposite.

3. Kevin Federline

I'm just going to let the aspiring rapper — famously, Britney Spears' ex — explain himself:

This particular "Brazilian ass-shaker" never made Federline's severely overwrought debut album, which arrived in 2006 to universal scorn and sold fewer than 20,000 copies by the time it went out of print. I wish I could be so self-satisfied about my own epic failures.

4. Payola

Pay-for-play: Illegal in many decades. iStockPhoto hide caption

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The practice of record companies paying radio DJs to play specific records is an old one — and an illegal one since 1960. So major record-label interests simply employed "independent promoters," complete with scare-quotes, to bribe stations and their employees with vacations, new clothes, illegal drugs — the usual. A pre-punchline Eliot Spitzer, then New York's attorney general, launched a massive investigation into the issue, eventually winning settlements totaling more than $25 million from three of the four major recording companies. Not only was this a terrible financial and publicity burden, but in today's commercial radio climate, the labels' songs — especially those from major artists — likely would have been played anyway.