Mario.

I would ask him how it feels to be milked so harshly. (I kid, I kid...)

Kratos

me: hey Kratos. how's your morning going
Kratos: I was on my way to kill Zeus and-...I SAID NO SUGAR!!! RAAAAAHHHHHHHH
me: uh.....check please

Zack Fair. Hearing his story through his own words and what he was feeling during those fucked up times has the potential to be a very different story than what's been told.

He seems as though he'd be an awesome guy too!

lara croft, meryl, and solid snake. Throw in crash bandicoot, now that would be epic.

There's place for discussion

From Tomb Raider: Lara Croft (any of the incarnations)- cool stories among 'other' things
From Uncharted: Nathan Drake & Victor Sullivan- decent banter
From Mass Effect: Garrus, Tali, Mordin, Jack, Wrex, Joker, EDI, Thane... err... most of the crew from ME2 actually.
From Deus Ex: JC Denton- I'd see if I could make him smile, nano-augmentations be damned!
From MGS: Solid Snake- The stories that guy could tell!

Poor Tifa, always getting friendzoned

And Aeris went and banged Cloud and Zack

Drake
Kratos
Organisation 13 (yes all of them)

Link, because it would be mindblowing to hear him speak more than two words in a row.

Rise Kujikawa...or Sully. Both would be guaranteed a fun time after too.