Ranking the Best Vince McMahon Feuds vs. His WWE Superstars

For 23 years, the evil Mr. McMahon character has made his presence felt across WWE television, making the lives of the company's top babyfaces a living hell.

Industry giants like Hulk Hogan, "Stone Cold" Steve Austin, D-Generation X and The Undertaker have all incurred his wrath, leading to unforgettable moments and angles that have spanned an entire generation.

In an era struggling to move on from the rebel vs. authority figure storyline, relive these 10 feuds that helped to entrench that trope in pro wrestling storytelling.

Bobby Lashley should have, conceivably, come out of his 2007 rivalry with Mr. McMahon as the next big star in WWE, but his departure from the company immediately afterward cost him the opportunity to dominate for the next decade and put the feud at the bottom of this list.

The result of the powerhouse representing Donald Trump in the Battle of the Billionaires at WrestleMania 23 and his role in the boss' humiliation on the stage he created, the feud saw ECW champion Lashley lose his title to the boss and endure countless beatdowns at the hands of the Chairman of the Board, son Shane and muscle Umaga.

Like any good babyface fighting from underneath in classic WWE fashion, Lashley overcame the odds and defeated McMahon to regain the title at One Night Stand in June 2007.

Then he abruptly left the company following a pay-per-view main event against WWE champion John Cena and ahead of what looked set to be a major push.

While it showcased maniacal McMahon, obsessed with revenge after having his head shaved and referring to himself as a hardcore legend, the fact that it was rendered meaningless hurts its standing.

McMahon's feud with CM Punk in the summer of 2011 should have meant more than it did.

Here was a brash, unapologetic and blunt anti-authority rebel in Punk, voicing his opinions about the empire the boss had built and the many cracks in it. He was red-hot in a way WWE had not seen in years and was the perfect representation of new, young and exciting blood pitted against the out-of-touch old man whose way of doing things had stunted his company's growth.

It was a story that wrote itself and, for a few weeks, became the most captivating thing in pro wrestling.

Punk taking shots at McMahon, using insider terms and shoot comments, caught the attention of fans and helped him crossover into popular culture. He should have been the catalyst for the latest, greatest run for the sport, but half-assed booking and questionable decisions doomed the feud.

The moment Punk won the WWE Championship and took off through the stands in his hometown of Chicago should have meant more than it ultimately did. Instead, the program became more about Triple H and Kevin Nash, and then Alberto Del Rio, than Punk himself, and the whole feud fell apart.

McMahon's disappearance from television just as the story gained momentum did not help matters.

It all began with a plot by the evil Mr. McMahon to use his family in a grand scheme against WWE champion "Stone Cold" Steve Austin. It was during the spring of 1999 that he set up his daughter, Stephanie, to be kidnapped and sacrificed to The Undertaker in a dark wedding.

She escaped the ritual, thanks to Austin, but never forgot her manipulation at the hands of her father.

Fast-forward six months to Stephanie's betrayal of Vince and alliance with Triple H, which would jump start one of the best stories of the entire Attitude Era.

The rivalry between father and daughter would be short-lived in that instance because of a grand family reunion at WrestleMania 2000. The same could not be said about their second go-round three years later.

In 2003, Stephanie was the general manager of SmackDown, establishing herself as a power player and standing up to the top stars in the business on a weekly basis. When her decisions went against the best interests of her father and she sparked a rivalry with his mistress, Sable, the showdown between the two was inevitable.

What no one could have imagined was the "I Quit" match between Stephanie and Vince that occurred at No Mercy 2003.

Vinnie Mac was at his most evil, exhibiting pure glee as he beat down his daughter, going as far as to choke her with a steel pipe. Eventually, Linda McMahon threw in the towel, bringing an end to her daughter's suffering, but the damage was done.

Surprisingly enough, the next time we saw Stephanie on television, she was back by her dad's side, where she has stayed ever since.

McMahon's relationship with The Undertaker has always been one of respect, but that does not mean the sports-entertainment icons did not go to war with each other on more than one occasion over the course of their three-decade relationship.

The Deadman and brother Kane bashed McMahon's ankle in 1998, the result of the Chairman berating them. A year later, Undertaker led a Ministry of Darkness and targeted McMahon's Corporation, leading to a battle for supremacy that lasted until the nonsensical revelation that McMahon was The Phenom's much-touted Higher Power.

When Undertaker returned to action after nearly a year away, sporting his American Badass persona, the first person he targeted was the billionaire owner of the company.

By 2003, the history between the two was well-known, so it was no surprise when The Deadman stepped up in defense of Stephanie McMahon in her battle with her father, immediately putting him in Vince's crosshairs.

After McMahon cost him the WWE Championship against Brock Lesnar at No Mercy, a Buried Alive match between the cornerstones of the company was booked for the Survivor Series pay-per-view. What ensued was a bloody, violent ass-kicking courtesy of Big Evil that was won by McMahon only after Kane interfered against his brother.

In the 17 years since that encounter, the two have crossed paths but not nearly to the degree they did before. Had they, this feud may have ranked higher on this countdown.

Prior to 2001, the hints at dissension between Vince and Shane McMahon had been either a ploy to sucker in a babyface or short-lived.

Then came father's ego trip and partial breakdown in late 2000, which saw him take on Trish Stratus as his mistress, leaving wife Linda in a vegetative state. When the opportunity to buy WCW and boost his ego even further presented itself, The Chairman of the Board was in all his glory.

Except, he did not account for one thing: a vengeful son rising a like a phoenix and coming back to take out his frustrations on the man responsible for so many of them.

Shane returned to the company, attacking Vince in a red-hot moment that immediately positioned the son as a major babyface in WWE. A few weeks later, on the March 26, 2001, episode of Raw, he did the unthinkable, buying WCW from underneath his father.

Six days later, at WrestleMania X-Seven, he defeated Vince in a Street Fight that remains one of the best examples of the company's grandiose booking.

The feud would continue into the summer and fall of that year as Shane and sister Stephanie battled their father as co-owners of The Alliance during the much-maligned Invasion storyline but lay dormant thereafter until 2016, when the prodigal son made his return to WWE TV for the first time in six years.

As long as Shane is his own man and Vince continues to pop up on television from time to time, the likelihood that they revisit their rivalry at some point is higher than most.

Who created Hulkamania?

It was the central question of the rivalry between the evil Mr. McMahon and Hulk Hogan on the Road to WrestleMania in 2003. Industry icons with egos as large as The Hulkster's pythons, they contested a war of words heading into the biggest show of the year.

McMahon went as far as to sign the contract for their showdown with Hogan's blood, gathered following a brutal assault on an episode of SmackDown.

In Seattle, at the Showcase of the Immortals, Hogan and McMahon both wore the proverbial crimson mask as they unloaded years of frustration and emotional torment on each other in a grand spectacle of storytelling. Hogan won despite an unexpected appearance by "Rowdy" Roddy Piper, but it would not settle the differences between him and his longtime business partner.

The feud would drag on through the spring and early summer of 2003, even including a take on Dusty Rhodes' Midnight Rider gimmick in which Hogan was suspended from WWE, only to return as the masked Mr. America.

Then it ended.

Not with a bang but a whimper, as The Hulkster took his ball and went home, leaving the storyline unfinished.

Unlike the Lashley and Punk feuds, the raw emotion and wealth of history that went into the program elevated it exponentially. Even without a decisive conclusion, it featured a marquee WrestleMania match and some stellar storytelling from masters of their craft.

It earns its place in the top five and, likely, would have landed even higher up the list had it been settled once and for all.

Triple H's rise to the top of WWE can be directly attributed to his feud with Vince McMahon late in 1999. The leader of D-Generation X and the top heel in the company, he took a great deal of pleasure in tormenting the boss, who got just as much joy out of making life a living hell for The Game.

Case in point, McMahon's inconceivable WWE Championship victory over Triple H.

The feud between the two escalated exponentially on the November 29, 1999, episode of Raw, when Triple H revealed that he had married an unconscious Stephanie McMahon during a controversial, to say the least, trip to Las Vegas.

That particular chapter of the rivalry culminated at Armageddon in December, when the heel benefited from Stephanie's shocking betrayal of her father to win the match and ignite the McMahon-Helmsley Era.

A little more than two years later, Triple H would earn the wrath of the boss again, this time for divorcing his daughter. Four years after that, he reformed DX with Shawn Michaels and make most of McMahon's 2006 miserable.

More on that one in a moment.

In 2007, McMahon put Triple H through the wringer at the No Mercy pay-per-view in October, forcing him to wrestle three matches in one night if he wanted to leave with the WWE Championship.

Like many of McMahon's best feuds, his history with Triple H is a long and winding road that will continue to add chapters as long as they remain active participants in the on-screen goings-on in WWE.

The worst thing Shawn Michaels could have told an egotist like McMahon in the winter of 2005 was to "get over Montreal" and "move on." After all, that night in November 1997 was one of the most important nights in the history of pro wrestling—one on which the evil owner of WWE derived great joy in screwing over Bret "Hitman" Hart.

Dismayed, McMahon took out his anger on The Heartbreak Kid.

He cost him championship opportunities, humiliated him and set the debuting Spirit Squad on him. After weeks of torment and mounting losses at the hands of the boss and son Shane, Michaels agreed to meet McMahon in a No Holds Barred Match at WrestleMania 22.

There, HBK got a measure of revenge, brutalizing both father and son before driving Vince through a table and putting an exclamation point on the beating with Sweet Chin Music.

A vengeful Vince returned the favor a month later, when he and Shane defeated Michaels and "God" in a tag team match. The beatings at the hands of The Spirit Squad continued and the professional manipulation raged on until Triple H came to the aid of his longtime friend, reforming D-Generation X and engaging the McMahons and their male cheerleader faction in a series of matches throughout the summer of 2006.

Ultimately, the babyfaces conquered the megalomaniac, his son and the massive Big Show inside Hell in a Cell at Unforgiven that September, bringing an end to a rivalry that lasted nine months and wrote many chapters throughout.

That it never got to the point where it was painfully repetitive to watch, even if some of the humor didn't land as fans had hoped, only elevated it on this list. Michaels' excellence throughout did not hurt, either.

When Bret "Hitman" Hart returned to WWE in November 1996, he found a company he no longer recognized. Gone were the days of traditional heroes and villains. In their place were shades of grey, seemingly encouraged by owner McMahon.

Though the chairman still called the action from ringside, with his official status as the boss unrecognized on television, his role became more and more apparent over the course of the next year. So much so that a frustrated Hart would shove him to the mat and berate him. Then, later in the year, he threw down with him in a hockey-style brawl.

Behind the scenes, Hart's contract was a topic of great stress as McMahon offered and then reneged on a 20-year deal that would have made Hart the Babe Ruth of WWE. With an incredible offer from WCW on the table, Hart decided to leave the company that made him a star, creating a schism with the boss he considered a father figure.

Frustrations between them, including Hart's refusal to drop the WWE Championship to Shawn Micahels in Canada after the company had spent eight months building him as that country's hero, boiled over. At the Survivor Series pay-per-view on November 9, 1997, the course of wrestling history changed forever when McMahon screwed Hart out of the title on a live pay-per-view broadcast.

It was the last time they would appear on television together for 13 years, when a reconciliation brought Hart back to WWE for an on-screen feud with McMahon.

Looking to settle the differences that had been well-documented over Hart's decade-plus absence, the Hitman and chairman clashed at WrestleMania XXVI in one of the night's marquee bouts. It was exactly what it needed to be: a one-sided ass-whooping that saw Bret unleash on Vinnie Mac, aided by the rest of the Hart family around ringside.

Hart's post-match celebration was well-deserved and the proper payoff to a feud that was, at once, both profoundly personal and undeniably legendary.

No feud in history meant as much to modern professional wrestling as McMahon vs. Austin.

Period.

Austin was the rebellious, anti-authority badass who balked at the idea of becoming the corporate champion McMahon wanted. What resulted was a rivalry full of twists, turns and Stone Cold Stunners for the chairman, the first of which occurred on the September 22, 1997, episode of Raw and sparked their rivalry.

From Austin's confrontation with Mike Tyson, which threatened the heavyweight boxer's business relationship with McMahon, to his refusal to wear a tie and jacket like the boss wanted, the early months were relatively calm compared to what the feud would become.

The hell-raising Austin would bring out the megalomaniacal side of McMahon, leading to the boss becoming the most hated heel in the industry. Their chemistry was magical, with the fans hanging on every instance of Austin's insubordination and jeering every attempt by the owner of the company to derail Austin's run at the top of the company.

Off-screen, WWE rose to unparalleled heights. The company enjoyed its greatest success, becoming a media juggernaut and promoting its Attitude Era to the masses. Fans ate it up, making Austin vs. McMahon the greatest rivalry in company history.

And one of its most enduring.

Even after injuries forced Austin into a premature retirement, The Texas Rattlesnake returned from time to time to stick it to McMahon, even participating in his public head shaving at WrestleMania 23 and dropping his entire family with stunners at the Raw Homecoming special.

Rarely do two characters come along at the same time, feed off each other to the extent that Stone Cold and Mr. McMahon did, exhibit the sort of chemistry they did and enjoy the type of success that they were responsible for.

It was a once-in-a-lifetime pairing WWE has tried, tried again and failed to replicate.

No matter how many other memorable feuds on this list there may be, none had the spark, chemistry or reach of this one.