My conclusion reached while attempting to think up my list for my own thread: it would be nearly impossible to do in 5 games

I think that I would start with Kirby Superstar Ultra and end with Shadow of the Colossus.

The big question is what three come between those two.

Funny you said that, my way younger sister just got into gaming for the first time by playing Kirby Superstar Ultra. Three more games to go until Shadow of the Colossus I guess.

Yeah, see, Kirby's great for that. Kirby's Adventure on the NES was my first really serious gaming infatuation, too.

If he/she haven't played anything, you should use power of wii. Yeah, thats right. Wii makes gaming easy & fun just like it says. Its nice portal to drugs that are worse... err I mean games.

Well, since I like to be slightly realistic, I'll go with all stuff I have access to atm.

1. Wii Sports (simple as gaming can be)
2. Flower (easy controls with the first inkling of a story wrapped in there)
3. Ico (again, simple controls, but shows off what I really enjoy about gaming personally which is storyline)
4. Psychonauts (to me this game has universal appeal, fantastic gameplay and hilarious storyline)
5. Valkyria Chronicles (a good intro to my personal favorite genre of gaming)

if that failed then they have different tastes than me and I'd have a much harder time helping them out.

I think I would put a puzzle game in there somwhere... have to come back with a list though

In no particular order

Wii Sports
Guitar Hero
Halo (1 or 3)
SSBB
Mario Kart

You need games that are interesting to someone that we would classify in the mainstream and easy to pick up and play. Some of you are crazy if you think showing an RPG to someone that has never played video games is a good idea. Although pokemon might work...

edit: Throw in GTA IV somewhere in there as well since their bound to have heard of it and would probably be interested to see what it's all about.

Can't I just give him a console. All I have to do is say 1 word, Wii, and give him a console and he will have endless fun with all the games on Wii.

But if I had to pick 5 I would tell show him the 5(6 if you count Wii Chess) deadly games.
Wii Sports
Wii Play
Wii Fit
Wii Music
Wii Sports Resort
and maybe Wii Chess if he/she is good.

Super Mario Bros. - obvious choice

Chrono Trigger - a user-friendly RPG that's not too complicated but still demonstrates how awesome the genre is

Super Metroid - easy to pick up and play but difficulty ramps up quickly. Best 2D action game ever made

The Legend of Zelda: Twilight Princess - pefection of the OoT-style, 3D Zelda. You have to admit if this was the first Zelda you ever played, it would be your favorite.

Metroid Prime - pinnacle of gaming (IMO).