Guilty Gear 2: Overture will be an absolute shocker to him, in a good way! $40 new at Game$top. That's $20 off. And of course you could get Guilty Gear X2 #Reload for the original XBOX, backwards compatible with the 360, for less than $10 used at Game$top.
Dead or Alive 4 might bring back the days of Street Fighter 2 for him. It can be had for cheap now.
Speaking of SF2, there's Super Street Fighter 2 Turbo HD Remix which will also be a shocker if he has an HDTV. $15, if I'm not mistaken.
To show him how far games have advanced since he left, The Orange Box is amazing for that. It's the quintessential "this is what video games can do today" game. Can also be had for rather cheaply.
I don't know if he made it to 1995 to play the original SEGA Rally, but SEGA Rally Revo will bring him right back to the Model 2 days. I got it $30 new at Game$top last summer.
And of course there is the plethora of classic arcade game ports released on XBLA. Teenage Mutant Ninja Turtles is an all-time favorite of mine. They're all rather cheap, and if they've got online play, they're an even better deal.