Best Two - Shawn Michaels
The heartbreak kid himself. At every level he has been at with WWF, he's really been the best. When teaming with Marty Jannetty, Shawn was one half of the most popular tag team in wrestling. They weren't top title contenders like the LOD, Demolition, or Harts, but dammit these guys were SO over with the crowd. They were the Hardy Boyz before the Hardys were cool, and they didn't have to jump off 20 foot ladders to do it.
After the great Rockers Split of the early 90's, Shawn became the best mid-card heel out there. It had been Mr. Perfect, but his back injury took him out of the running, and the cocky Michaels easilly became the definitive heel in the IC Title picture. Having the announcer let people know that "Shawn Michaels has left the building" a la Elvis Pressley was classic.
Then, Shawn became WWF Champ, and though never the best draw, the guy put on some of the best big-stage matches ever. He switched from face to heel and back again, SEEMLESSLY. He helped get Austin over, he was a major player in the Screwjob and the Team Canada angle, and he pulled emotions for everybody when he returned against Triple H.
Nobody else has the PWI Match of the Year resume Shawn has. NOBODY. He OWNS the award. He has won the last four (2004 vs Benoit and HHH, 2005 vs Angle, 2006 vs McMahon, 2007 vs Cena) and won 4 straight in the 90's as well (1993 vs Jannetty, 1994 vs Ramon, 1995 vs Diesel, 1996 vs Hart). Nobody else has ever won 4 straght MOTY's (Sammartino won three straight once), and Michaels has done it TWICE!
So it's damn near impossible to pick his two greatest matches of all time, but we'll try!
vs Marty Jannetty, Royal Rumble 1993
The match that stole the night entirely. As good as Bret vs Razor was, the Michaels vs Jannetty match was a clinic, and I still feel it's one of the 5 best IC Title Matches of all time, and the only one in the top 5 featuring a title retention. Jannetty had just returned from facial injuries after the Michaels heel turn, and accidentally smashed a mirror on Sherri's face. The storyline wasn't just Marty's hatred for his former partner, but on which side Sherri would appear.
In the process, these two men put on a CLINIC of face vs heel psychology, near falls, and making a crowd eat out of your hand. Jannetty had the title won on 4 different occassions, including the rare slingshot into the ringpost moment when we ALL thought it was over. Botched interference by Sherri on Marty's behalf allowed the heel Michaels to escape with the IC Belt in classic heel fashion.
vs Kurt Angle, Wrestlemania 21
The longest match of the night, and not a second was boring. I used the word "clinic" in my write up of Jannetty vs Michaels in terms of near falls. Well, this match was a clinic of reversals. Ankle locks abound, and you never really knew if Shawn would tap, reverse, or get to the ropes. Angle won this war after nearly a half-hour, and the fans ate it right up. Angle showed people that he had arrived as an all-time great, and Shawn is a big reason for it.