Mr. McMahon's Best Year As A Heel?

[The Rick Jericho]

There is so much. 1998 was the genesis. 2001 was a fun run. 2003 was perverted daughter beater. 2006 was just ridiculous. 2007 was do-rag.

[Deleted]

1999 -



AW SON OF A BITCH!

[clifford]

In 1999 Vince Mcmahon was the most over heel in wrestling.

I'll never forget as an 11 year old my jaw hitting the floor when he came out all jacked for the 99 Rumble.

I HATED Vince in 1999. He was just so evil.

[David-Arquette was in WCW 2000]

1998. When I think 1999 I just think of all the higher power crap. He was great at the start of 2001 but after that I just never really cared for the character, outside of a few moments here and there.

[thecrusherwi]

I think any of the earlier years are acceptable answers, but I prefer 1998. He starts the year as normal Vince who's not all that dissimilar from announcer Vince and through his battles with Austin slowly slips into madness. It's almost like a week by week progression of slowly losing his grip on reality.

[Jiren]

1998 gave us this slice of awesomeness

www.youtube.com/watch?v=sFg-qCSeLXE

[Deputy Muscle]

98 because he was so fresh and believable.

[mysteriousagent0076]

There are too many but if I had to pick one I’d go with 1998. The skit where Austin fills McMahon’s Corvette with concrete is one of my favorites...the look on his face as it’s happening...

It’s a shame that wrestling can’t go back to those days. I miss actual characters and wrestlers with charisma who are actually fun to watch. 

[The Rick Jericho]

Hey... someone actually voted for Do-Rag McMahon!

YES!

[thegame415]

98 is the best.

2003 is underrated.

[agent817]

I am going with 1998 Vince on this one. It is not even a contest.

[Aceorton]

The early part of 1998 was a fascinating slow reveal where we found out the guy who'd been an uptight dork announcer for 20 years, and who'd been outed as the owner in the previous year, was actually more vile and pompous than any of his wrestlers. Nothing that came afterward for Vince was anywhere near as captivating.

[Deleted]

he was still evil and great in 1999 (I mean the guy had his own daughter kidnapped by the Undertaker), but it's gotta be 1998

I love going back and watching/listening to him on commentary in 1996, knowing what he'd become just two years later. lol

[TGM]

1998 he just didn't like Stone Cold as champion.

1999 he had merged his corporate security team with an armageddon death cult that had attempted to sacrifice his daughter.

I can't decide

[Slanted and Enchanted]

I love cartoonish heel Vince from 1999 and beyond. But 1998 was his coming out party. He started off as a 'good guy' but slowly broke out of his shell and we saw him for the rat bastard he truly was.

[rrg251]

Early 99, through Wrestlemania. His face following Austin's win makes the whole Russo-y slog worth it

[lionheart21]

1998 Heel Vince is up there with some of the all-time greatest heel acts

["Gizzark" Mike Wronglevenay]

In 2007 I think he did a good deal of his finest work. The du-rag ECW stuff was gold, albeit pissed away predominantly on Lashley. He also drew one of the biggest buyrates in company history; that hair match was definitely one of the main events of the night.

[somsta]

1998. Over the other years there was some good to great moments, but for the most part, everything past Mania 15 just feels like stale attempts to redo the lightning in a bottle of 1998.

[Starshine]

'98, then it's all downhill from there.

I think he hit rock bottom around late 2001/03 era. Where he basically became a self-indulgent parody of the character. The only real standout memory since then was probably the Vince McMahon Appreciation Night, where the entire roster all derided him for being the worst person imaginable. Just pretend the dumb limo explosion thing at the end didn't happen.