I’ll echo Jragon. The handheld games are the core games in the Pokemon franchise. (Just in case you didn’t know, Pokemon is a Nintendo exclusive) A DS Lite with either Diamond or Pearl is the way to start. Once he gets beats that and wants to add more Pokemon, you can back fill with the Game Boy Advance games (Emerald, Ruby, Sapphire, Fire Red, Leaf Green), which can be played on a DS. Be aware there’s a lot of redundancy between the games. Diamond and Pearl are basically the same game, but there’s about 20 Pokemon exclusive to each version. The story line is identical. Similarly Ruby and Sapphire overlap, and Emerald is a superset of both. Fire Red/Leaf Green is the last pairing.
Some of the side games are fun, but not the best place to start. Pokemon Ranger made innovative use of the DS touch screen and was extremely addictive. I think I cleared more levels than my kids.
The Pokemon Mystery Dungeon games are basically the old UNIX classic Rogue with really cool graphics and Pokemon as the main characters. However, there’s a lot of reading involved, which caused my 5 year-old to give up. My 8-year-old has no problem.
Console-wise, you can pick up a used Gamecube or a new Wii and a copy of Pokemon XD. (Wiis play GameCube games, but you need to get your hands on a GameCube controller). I picked up a used GameCube right about the time the Wii was released. I found one with the XD game on eBay for $50.
The only Wii Pokemon game currently available is Pokemon Battle Revolution, which is pretty weak as a standalone game. It’s like Nintendo suddenly realized, “Oh crap, this console is selling like mad, we already got a Mario game, what about our #2 franchise? Quick, put something, anything, Pokemon on the Wii”. Basically it lets you copy your Pokemon from the DS games to the Wii’s internal memory and watch them battle in 3D. If you don’t have a DS there are a few canned sets of Pokemon to battle with. It’s a fun expansion to the Pokemon universe, but in no way worth the $50 retail price. $20 after a price drop would be more reasonable.
Like other posters mentioned, GameStop has the Deoxys giveaway this weekend and next (my wife was supposed to take my sons there today on their first day of summer vacation), which makes now a good time to start. What’s a Deoxys giveaway? Let’s see… There are 493 Pokemon in the Pokemon universe. The object of the game is to “catch 'em all”. However, it is impossible to obtain all of them by playing the game normally. Some of the rarer ones are locked away in the game code. To release them, you need to go to various Nintendo events, such as this GameStop promotion and unlock the Pokemon via the Wi-Fi connection built into the DS. Usually the events are corporate synergy tied to some other Pokemon merchandise. For example, last month Toys R Us had a Darkrai event giveaway to coincide with the release of the Darkrai movie DVD. (In Japan, where the films still play in theatres, the giveaways were in the theatres showing the movie).
Whoa, this is a long post. Seeing as I have 2 Pokemon addicts for sons, I’ve picked up a lot more knowledge than I’d realized. We haven’t even mentioned the trading card game…