There were a lot of huge names in WWE during the Attitude Era but the biggest heel of that period of WWE history was easily Vince McMahon. While Degeneration X, The Undertaker, Mick Foley and the rest of the Attitude Era stars helped win the Monday Night Wars, it was the feud between the rebellious Stone Cold Steve Austin and evil boss Mr. McMahopn that started it all.
While WWE is trying to reignite a similar story with Shane McMahon now, there was no replicating the dastardly villain that was Mr. McMahon. While Shane can do more in the ring that his dad, his father brought such a passionate response from fans that even his lesser matches won over the crowds, wanting to see the old man get what was coming to him.
10 SHAWN MICHAELS (BACKLASH '06)
The feud between Shawn Michaels and Vince McMahon was starting to get really heated in 2006 and eventually led to Degeneration X reuniting to battle the evil boss. However, at Backlash 2006, Mr. McMahon was mocking Michaels' newfound Christianity and displayed a very sacrilegious angle.
McMahon demanded that Michaels team up with God to battle he and Shane McMahon. In what was basically a handicap match, Michaels held his own against father and son and actually kept it even for almost 20 minutes before he took the advantage and tried to put both Vince and Shane through a table before The Spirit Squad interfered and Vince won the match.
9 BOBBY LASHLEY (ONE NIGHT STAND '07)
When one thinks of Bobby Lashley and Vince McMahon, most people head to the match where Lashley beat Umaga at WrestleMania to allow Donald Trump to shave McMahon bald as part of the stipulation. This match at One Night Stand 2007 was actually a title match and, crazily enough, Vince McMahon was the reigning and defending ECW world champion.
McMahon had Shane McMahon and Umaga with him as he defended his title against Lashley. The three men all took turns beating down Lashley but it didn't matter as eventually he destroyed Vince with a chair and hit the spear to win the title in 12 minutes. The next night on Raw, McMahon was murdered when someone blew up his limo.
8 TRIPLE H (ARMAGEDDON 99)
While Mr. McMahon was feuding with Stone Cold Steve Austin through most of the Attitude Era, there was also the case of Degeneration X making his life hell. Triple H wanted revenge against Mr. McMahon for costing him the world title and he challenged McMahon to a match at Armageddon.
This was also the angle that had Triple H got Stephanie McMahon drunk and drove her to Vegas to marry her, ruining her relationship with Test in the process. If Vince beat Triple H, the marriage would be annulled. This was a No Hold's Barred match and lasted almost 30 minutes before Stephanie came out and interfered to help Triple H win.
7 RIC FLAIR (ROYAL RUMBLE 2002)
In 2001, Ric Flair returned to WWE and revealed that he had purchased all Shane and Stephanie McMahon's stock in WWE, which made him an equal partner to Mr. McMahon when it came to running the company. This clearly made the two enemies, as McMahon wanted the control back and Flair just wanted to make life hell for the Chairman.
The two men fought in a street fight at the 2002 Royal Rumble. Flair was still able to go at this point in his career and he took an early advantage over McMahon until Vince brought weapons into play. McMahon even went for the Figure Four. After 14 minutes, Flair used a low blow, TV monitor and lead pipe on McMahon before making Vince tap to the Figure Four.
6 STEVE AUSTIN (ST. VALENTINE'S DAY 99)
The man that fans loved to see beat up Mr. McMahon over anyone else was Stone Cold Steve Austin. This was the feud that ignited the Attitude Era and Stone Cold was the hottest babyface in WWE history. When it comes to actual matches, the best fight the two ever had came at St. Valentine's Day Massacre in 1999.
This match took place after McMahon won the Royal Rumble and then said he didn't want the world title match. When he was told that meant the runner up -- Austin -- got the match, it incensed McMahon. That led to this steel cage match. The match only lasted seven minutes, but the entire time saw Austin just destroy McMahon. The end came when Big Show made his WWE debut but accidentally threw Austin threw the wall of the cage, giving Stone Cold his WrestleMania title shot.
5 HULK HOGAN (WRESTLEMANIA XIX)
It seemed that through the 2000s, Mr. McMahon ended up fighting everyone that he helped create, from Shawn Michaels and Bret Hart to Stone Cold and Hulk Hogan. When it came to Hogan, the match took place in 2003 and was one of the top matches at WrestleMania XIX.
Their feud started when Hogan was feuding with The Rock and McMahon came down at No Way Out to interfere and help Rock win. McMahon then said that Hulkamania was officially dead and he hated Hogan for leaving for WCW. That set up this match, where if Hogan lost he had to retire. This was a street fight and the two ended up both bleeding by the end. Rowdy Roddy Piper tried to interfere to cost Hogan, but Hulk hit his leg drop and pinned McMahon.
4 DX (SUMMERSLAM '06)
The feud between Mr. McMahon and Shawn Michaels stretched throughout 2006. While Michaels was forced to team with God at Backlash, he got a human partner at SummerSlam when Degeneration X reunited and the two took on Vince and Shane McMahon. This was Triple H's first time to turn face since 2002.
As with many of the matches that year, The Spirit Squad was there to help Vince and Shane McMahon, as were Finlay, William Regal, Mr. Kennedy, and Big Show. The McMahon's taunted tag teams of the past with the Hart Attack and Doomsday Device. Despite all the interference, Shawn hit Sweet Chin Music on Vince and Triple H hit the Pedigree for the win.
3 SHANE MCMAHON (WRESTLEMANIA X-SEVEN)
In 2001, WCW went out of business and WWE purchased the company. Vince McMahon and Shane McMahon were already feuding because of how Vince was treating Linda McMahon as well as Stephanie McMahon. The big twist when WWE announced they purchased WCW was for Shane McMahon to come out and announce he was who bought the company and was going to war with his dad.
Vince McMahon had also fired Mick Foley, but it turned out Linda McMahon had given Foley a contract before that to referee a match at WrestleMania X-Seven and that match would be a street fight between father and son. All four McMahon's got involved, with Stephanie taking her father's side and the match ended with Linda low blowing her husband and Shane hitting Coast to Coast to win.
2 DX (UNFORGIVEN '06)
While DX beat Vince and Shane McMahon at SummerSlam, Vince wasn't finished yet and set up another match. Since The Spirit Squad couldn't seem to get the job done for the McMahon's, they enlisted Big Show instead. This match was a Hell in a Cell match with DX taking on Vince and Shane McMahon and Big Show in a handicap match.
The match, despite the disadvantage, went to DX. They pulled out all the stops, wrapping a chair around Shane's head and Michaels dropping an elbow on it to remove him from the occasion. This was also the match where they pulled down Big Show's tights and shoved Vince's face in there. Triple H used his sledgehammer on Vince for the win.
1 SHAWN MICHAELS (WRESTLEMANIA 22)
Out of all the matches in 2006 between Vince McMahon and Shawn Michaels, the best of them all, and the best match of McMahon's wrestling career came at WrestleMania 22. This was a singles match between the two and was a few months after McMahon cost Shawn his chance to win the Royal Rumble.
As with most of McMahon's best matches, this was No Hold's Barred, which allowed WWE to cover up Vince's lack of in-ring skills. The two battled for 20 minutes pulling out all the stops. It finally ended when Michaels put a trashcan over Vince's head, laid him on a table, climbed a ladder, and dropped the elbow. Sweet Chin Music then ended the match with Michaels beating Vince McMahon at the biggest event of 2006.