Seeing the sales for Next-Gen systems, and everyone saying that this generation so far is so different in that respect from all past ones has gotten me to wonder if it's that different from the 16 bit generation. I think it's really very similar, you only have to reverse the roles of consoles and handhelds.
DS is Super NES, the most popular (in Japan by far and in the US by not so much) with it having the lion's share of the best games and the most 3rd party support.
PSP is Genesis. Like it's predecessor it has a bunch of extra "features" (think Sega CD and 32x) that cost a lot of money, but in the end aren't all that necessary. It certainly has its great games and a strong fanbase, but in the end Super NES is more popular.
Wii is Game Boy. It doesn't have the best graphics/specs, but it has the games (first and third party) that make it not matter.
Playstation 3 is Game Gear. Much better specs than Wii, about double the price, a few games that make it worth buying if you like their franchises, but ultimately eclipsed by Wii's hype.
The only thing is I can't quite place Xbox 360. In Japan, it seems like Lynx's few games that make the audience want it, but its too popular in the US to have that distinction.