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RealPlayer, though hard to believe, is nearly 17 years old this year. Available on a wide variety of platforms, and even on mobile devices, in theory it could be one of the best media players on the planet.
But the sluggish, slow and packed full of crapware software was nothing but a plague on millions of computers worldwide. Spyware was even found to be in the software, which led to a massive boycott and controversy surrounding the company that makes the software.
Though it supports MP3s, MPEG-4 formats, QuickTime and Windows Media formats, the only reason anyone would use it is if they were forced to, by needing to view or listen to its propriety RealAudio and RealVideo formats.
It's no VLC, suffice to say.
When Sony declared a war on software and music piracy in 2005, little did the world consider that the company could be putting malware on the discs it sold.
When the CD was inserted into a computer, it would install a rootkit invisible even to the most advanced anti-spyware or anti-virus software of the time. But Sony was found up the creek when hackers and cyber-attackers would use the same rootkit to hide malware of their own to capture keystrokes or steal data.
Over half a million machines were infected, which was only made worse by a "fix" that Sony brought out to try and solve the problem. Lawsuits flew everywhere as a result, and Sony was left very red-faced after the whole incident.
Poor old Alan Sugar. Founder and chief of British firm Amstrad, he may have missed the boat on the email revolution.
Released weeks after the millennium, the part-landline, part-email 'machine' cost £79.99 (nowadays, that would be £130, or $199), and an additional 12p ($0.20) to send each email. It was a total rip-off and difficult to use. Had it been released a few years before hand, it could have made a ton in sales.
But while computers and modems were still expensive, the Em@iler was just late to the game.