Your Hail Mary comment got me thinking: is there an example of Hail Mary working in the tech biz? I've seen it happen in football enough to know it's at least worth a shot. But launching a product with all kinds of problems into a competitive market?
The original iMac. Same crap in a prettier package, and it saved Apple.
I was surprised that Google Apps caught on, but I'd underestimated Microsoft's lethargy - they had reportedly developed a web version of Office 2003 but decided to sit on it.
I would actually reckon that the NES was Nintendo's original successful Hail Mary. The games market was dead, introducing a new game console at that point was suicide. They coasted through the SNES due to a lack of real competition (Genesis being the only threat) and name recognition. They flopped the N64 and Gamecube for being more of the same. They've always had innovative ideas in the marketplace; The gameboy, the Virtual Boy, the Famicom Disc System, the Satellaview, the SuperFX chip, rumble paks, minidiscs, etc.
The Wii was just returning to form in fabulous style. They weren't hinging the success of their entire company on a low-chance market like they were with the NES, or Apple did with the iMac. Nintendo has (and had) plenty in reserves and a handheld that printed money if the Wii failed.
Final Fantasy on the NES. That's supposedly what the "final" was for; it was to be their last game before the studio shut down. It was a hit, and it and its successors kept them in business until they morphed into Square Enix and became Japan's EA.
That pretty much describes the MMO industry. I remember beta testing EVE Online and being amazed when they launched it. Yet, it's still going strong how many years later.