Although I love Taker, I will always put VADER ahead of him in terms of big guys that were awesome in-ring workers (Though I'll admit I'm a Vader mark).
As for who can challenge Taker for the greatest of this generation? That's pretty damn easy. A man who despise being out for 3 to 4 years still continues to put on great match after great match, a man who despite his checkered past is still (Arguably) the single greatest in-ring performer of all time (Yes, he might be ahead of Flair).. Of course, I'm talking about SHAWN MICHAELS!
For as good as Taker has been these past couple of years (As far as in-ring work is concerned), his matches weren't all that good during the early to mid 90's (It wasn't until he started having matches with the likes of Bret, Austin and yes, HBK, that people started to notice of Taker's in-ring abilities), though I will admit that when you're feuding with the likes of Yoko, Nash and Giant Gonzalez you can't put on classic matches.
Back to Shawn, here's a couple of his matches that were flat-out great (With the date included for those that may want to check them out).
The Rockers vs The Brainbusters (3/18/89)
The Rockers vs The Hart Foundation (Various dates)
The Rockers vs The Orient Express (Various dates)
Yes, I'm starting with the tag matches. This is when people started noticing that this Shawn guy was pretty damn good.
vs Mr. Perfect (3/17/91)... One of Shawn's earlier single matches, and he managed to hang with another awesome in-ring performer. This is still only the tip of the iceberg.
vs Bret Hart (11/25/92).. I believe this was Shawn's first time main eventing a PPV (It was Survivor Series, by the way) and Michaels did not disappoint as he went toe-to-toe with the champ and they put on their best match together. Of course, Shawn and Bret would be involved in a fairly big moment at SvS some years later.
vs Marty Jannetty (1/24/93/Royal Rumble 93).. This was a match that was more than 1 year in the making after Shawn turned on Marty. They went on to steal the show with their match.
vs Marty Jannetty (7/19/93).. If they stole the show at the Rumble, then on this night they decided to tear the house down. Marty had the best mach of his life, and of course, Shawn did his usual great job.
vs Razor Ramon (3/20/94/Wrestlemania X). This was a Ladder Match. You might have heard of this one. It was ahead of its time, and although it doesn't hold up well (At least when compared to the Dudleyz/E & C/Hardys ladder matches), its still for many THE defining ladder match.. Here's the fun part, it wasn't their best ladder match.
The Royal Rumble 95 :Shawn was the first entrant in the Rumble, and still won the match after British Bulldog thought he had gotten rid of Michales. Shawn skinned the cat and threw out BB for his first Royal Rumble victory, and his most impressive RR performance to date.
vs Jeff Jarrett (7/23/95). Much as he did with Razor and Jannetty, Michaels once again found himself being a part of someone else's greatest match. This time it was JJ. This happened at the second In Your House PPV, and Shawn won the match and the IC Title (At this point I started realizing that HBK was pretty damn good).
vs Razor Ramon (8/27/95). The OTHER Ladder Match, which I've always thought was better than their first. In this match, both men learned from theor previous encounter and avoided the spots that had damaged them the first time around (Psychology in a ladder match? Yes, it can be done).
vs Owen Hart (Can't remember the exact date, thought it was on RAW). This match was decent, but its mostly remembered for the Enziguiri by Owen and Shawn's AWESOME selling job as he had everyone believing that he was badly injured. I remember hating Owen for a long time after that :(
vs Owen Hart (2/18/96). Now THIS match was ace. This would be the return bout after Owen took him out. Shawn put up his WM title shot on the line and won. At this point, Shawn was pretty much unable to put on a bad match.
vs Bret Hart (3/31/96/Wrestlemania XII). Now just a great match, but two of the most memorable moments in the past 20 years. Shawn coming down on a zipline from the rafters, and Shawn hitting that second SCM (Vince:Michaels got all of it!) to win his first title. The childhood dream has come true, for Shawn Michaels.
vs Diesel (4/28/96). This was a No Holds Barred Match and SURPRISE! Shawn leads Diesel to the best match of his life. This took place at IYH:Good Friends, Better Enemies. Worth tracking down just to see Diesel actually try inside the ring.
vs British Bulldog (6/23/96). One of Bulldog's better matches in his career (Only his match against Bret at Wembley and his match against Owen for the Euro Title were as good as this one). This one happened at King of The Ring, and it was probably the closest Bulldog came to winning the WWF Title.
vs Vader (8/18/96). According to legend, Vader was supposed to win the strap here. Michaels threw a hissy fit and ended up retaining the title... But only after Vader's best match in WWE (SURPRISE!) which had Michaels selling like a mad-man for the big guy.
vs Mankind (9/22/96). The match that Mick Foley himself calls the favorite match of his career. Probably Foley's best straight up singles match, and probably the best WWF match in 96.
W/ Steve Austin vs Owen Hart & British Bulldog (5/26/97). At the time, this was arguably the best tag-team match I'd ever seen. It was one of the first time where we had partners that didn't get along (Sup, Russo?)
vs The Undertaker (10/5/97). One of Taker's first truly great matches. This was also the first HIAC (And still the best, as far as I'm concerned) and it had Shawn winning the match after Kane made his debut and Tombstoned Taker. Most wrestling publications and/or critics had this as the best match of 97.
vs Bret Hart (11/9/97). A rabid crowd, Shawn was at the top of his game as Canada wanted to kill him. A match that gets no love due to some small incident that happened afterwards (Which might have led to the most successful period in WWF/WWE history).
vs The Undertaker (1/18/98). This was the famous (Infamous?) Casket Match where Shawn injured his back. The best Casket Match in WWF history.
vs Steve Austin (3/29/98). Decent match, but an important one since it was the "passing of the torch" to Austin. This was also Shawn's last wrestling match. Until...
vs HHH (8/25/02). After being away for four years, Shawn comes back and looks just as good (If not better) as he did during the 90's. On a LOADED Summerslam card, he manages to steal the show once again.
vs HHH, RVD, Booker T, Kane & Chris Jericho (11/17/02). Shawn wins his last World Title (Up until this point) and puts on a show-stopping (SEE WHAT I DID THERE!) performance in the first ever Elimination Chamber match.
And, the rest...
vs Jericho (WM 19)
11/16/03.. This was at Survivor Series. Shawn was the only guy left on his team and he almost single-handedly won the match. He ultimately lost to Orton (with some help from Batista) but managed to once again steal the show.
vs HHH (12/29/03). His best match against HHH. This happened on the last RAW of 03, and although it had a screwy finish, it didn't prevent it from being one of the best matches in 2003.
Continued in the next post.