Well, you'll wanna make a good first impression. The orginal LoZ isn't going to convince anyone.

I'd show them something like Guitar Hero or Wii Sports first, to get them interested, then move onto something like MGS4 or GTAIV to show them how sophisticated games can be. THEN, I'd show them the classics.

You are going about this all wrong. Really, really.

But shit, five games? Damnation!

I'm going to have to think on this one a while.

C'mon. You put FF6 or Ocarina infront of someone who's never played a game before or has a low opinion of them, they'll just think games are stupid.

Super Mario Bros. 3
Chrono Trigger
Metal Gear Solid
God of War
Civilization 3

GTAIV is not what you use to initiate people after Wii Sports. Criminy. That will make them think games are stupid.

Ocarina's stood the test of time well enough to be included in this list - way before any of the Grand Theft Autos.

People are not going to be impressed by "sophistication". That comes across like a comic book nerd trying to show people how awesome graphic novels are using Sandman: he's right, and Sandman is fantastic, but he still comes across like a nerd trying to puff up a medium that has nothing to it.

Focus on the fun of it, first. If you want to get into sophistication, finish out with it.

I have to think on this for a while but any list that has only Sony or only Nintendo is an automatic fail in my opinion.

So every gamer became interested in games in the past 5 years? Everyone thought they were stupid until the current generation?

Now, this guy we're doing it for - a skeptic, you say? Just doesn't see what they're all about?

I guess I'd recharacterize as more aloof than a skeptic: he's aware they are potentially a lot of fun, but just doesn't have the drive to immerse himself in something that he views as ultimately nothing more than gainless fun.

I would probably use these games:

Mario Kart Wii (Or any similar racer): It's a game that I think would be easy to get into. Mario is a well known character, so it wouldn't be completely foreign to them. At the same time, it will get introduce them to single player experience, multiplayer experience, the idea of unlocking things and so on. At this point in time, it's a rather closed experience, nothing is open to go exploring.

Super Mario Galaxy (Or any similar platformer): Sticking with the new games still. I think the platformer would be the best genre to move to next. There's a fine display of graphics here, it's really fun, there's things to collect in order to unlock things. It also introduces the idea of story within a game, although simplistic, I think it's a good idea to start with stories like this.

Bioshock (Or any similar First Person Shooter): I haven't played this myself, except in demo form, but from what I have heard and played it's good for plot and gameplay, whilst it also shows off graphical excellence. This would take the take the player to a more mature idea of gaming - getting rid of the idea that games are only simple and for children, and offering them some plot and tactics.

Final Fantasy IX/Final Fantasy VIII (Or any similar RPG): Starting to take things alot further now. These two games I think would show them, that you can get alot out of a game, and that a lot of effort goes into them. There's the story, the characters, the graphics, the music etc. Although I'm taking them back to the PS1 generation, I think the FMV scenes would ease them into these sort of games, and perhaps wouldn't mind the graphics once they start playing and getting into it more. I'd like them to get the idea, that you're not always restricted, and you can go and explore, battle, play card games, ride chocobos when you want etc.

Maybe end with a sand box game like Oblivion or Grand Theft Auto.

I've only got four games here which I discussed in a little depth. And I'm not sure if it would work. But I thought that would be the general kind of order I would do things. Maybe it'd be better to show them a few more game of each genre, but that's what I came up with by sticking to the rules of the thread.