Remember the guy in high school who was effortlessly, totally cool? And then there was the kid who tried desperately hard to be hip, but could never quite pull it off? Well, Richard Branson personifies the former, and Larry Ellison, the latter. It's uncanny, Ellison is taller and richer than Branson, and his private island is bigger. He's also a licensed pilot who owns a fighter jet, and a champion yachtsman who's won the venerable America's Cup. Ellison is a self-made success whose name was, no joke, inspired by his adopted father's experience on Ellis Island. Oh, and he founded Oracle ( ORCL), one of Silicon Valley's most respected and resilient companies. But for all that, Ellison is still just an unlikable geek with the Oracle sobriquet of "LPOD" -- "Larry Prince of Death." Of course, what do you expect from a guy who's a fan of the Genghis Khan quote "It's not enough that we win; all others must lose." Plus Ellison's too-much-is-never-enough materialism is, well, just too much. The $110 million Woodside, Calif. estate, the Newport "cottage," the Malibu mansion, the four trophy wives, the 454-foot yacht, the private golf course, the million-dollar sound system that uses a drained pool as a subwoofer: taken together, it's all just . . . uncool -- a sadly bad parody of Jay Gatsby. In short, while literature memorializes the tragic figure who spends their life trying too hard to be something they're not . . . history doesn't. Follow @AndrewKosztyoThis article is commentary by an independent contributor, separate from TheStreet's regular news coverage.