Chris Jericho's two standout matches are Fully Loaded 2000 and No Mercy 2008. I think I have both at **** 3/4. WrestleMania XIX is a splendid match, but it wasn't the show stealer for me. That honor goes to Rock/Austin III, and it didn't frankly steal the show. It was
Lesnar had a lot of great matches in his short span at the top of WWE, which is pretty much his entire career. His absolute best is the Iron Man match against Angle followed by the Benoit match from SmackDown in December of 2003. After that, I'd say it's between the HIAC match against 'Taker and the SummerSlam '03 bout against Angle. Obviously, I haven't watched his "extreme" match against Cena--while typing all of this.
It might be difficult for me to form a "best of Triple H," but my 5 favorite matches of his would be (as they happened) Royal Rumble 2000 (Foley), Judgment Day 2000 (Rock; probably my all time favorite match), SummerSlam 2002 (Michaels), No Mercy 2008 (Jeff), and WrestleMania XXVII (Undertaker).
When we say "Triple H's generation" what are we talking about - the last 10 years? Because Undertaker has had a ton of big time quality and classic matches in that period too along with Michaels.
Perhaps, the past 12 - 14 years, or even break it down to the years after Hunter and Michaels formed the original DX. That would be "Triple H's generation."
On the whole "classic" thing, for me, a 5-star match or a near 5-star match is a classic. The definition. The rest are incredible matches, but not necessarily--classics. There are exceptions, obviously. For example, Rock/Hogan IS a classic; so is Hogan/Andre, personally.