That's a whole lot of video game right there for someone who sounds like he isn't that into video games (I mean, it sounds like he has skipped out on some of the best games over the past 5 years, and they were all released on console) If his interest is just getting to complete these games, I would suggest he start with Batman: Arkham Asylum (easily the most concise (*cough*andbest*cough*) game there) and perhaps doing coop with him in Saints Row the Third. I would use Burnout Paradise as a pallet cleanser, playing that when he doesn't fancy playing anything in particular as it's just a great game just to have no real aim or objective with.
As great as Mass Effect 1 & 2 and the Ezio games are, I have to wonder if he is really going to get through these. They are each huge games that suck up a lot of time and attention. It's fine when these games are played years apart, but back to back? Anyway, I would recommend he go in order of release (so Mass Effect, Assassins Creed 2, Mass Effect 2, Assassins Creed: Brotherhood) with the advice that as soon as he get's bored, he moves onto the next game and come back to it later, or play Burnout Paradise. As for Arkham City, that'll depend on how he got on with Arkham Asylum, If he loved AA, then he should play AC right away. If he's not fussed, that can probably go to the back.
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