19. Sega Saturn - 21st Century
To be fair, the commercial is worse than it should be due to hindsight bias: we all know what an awful debacle the Sega Saturn turned out to be, so when the evil gray mystery face asks us if we're "ready" for it, it's hard not to laugh a little. Luckily, some goofy douchebag in a Twilight Zone-esque void starts dancing around a television set, babbling nonsense and giggling to himself, which makes it really easy to laugh at this commercial. Really, it looks more like an experimental student film more than a commercial for a major videogame console release. And the saddest thing of all? The whole commercial hinges upon the Saturn as being a glimpse into the 21st century, when in fact the console would collapse in on itself by 1998.
Also, "Twenty Spleen-Busting Games At Launch"...maybe don't promote your system by claiming it will cause major organ failure, Sega.