Mr. McMahon and Shane McMahon—theirs has always been the kind of on-again, off-again father-son relationship that, when "off," would make cringe the likes of Cronos and Zeus, Ryan and Griffin O'Neal, and Darth Vader and Luke Skywalker. And at WrestleMania X-Seven, the "off" was definitely on, thanks mostly to the WWE Chairman's flagrant extramarital affair, plus his insatiable appetite to crush the opposition.

To fully appreciate the severity of this dysfunctional family feud, one must journey back to December 2000, when Mr. McMahon had finally had enough. Deciding his wife, WWE CEO Linda McMahon, had interfered too much in the way he ran his company—evidenced by the fact that she appointed Mick Foley as WWE Commissioner—he publicly informed her, "I want a divorce!" Linda, devastated by her husband's cruel declaration, suffered a nervous breakdown, though her collapse would leave Mr. McMahon anything but grief-stricken—unless laughing uncontrollably, assuming Linda's authority as WWE's CEO, immediately firing Foley (at Christmastime!) and engaging in a very open affair with Trish Stratus was simply his way of "coping."

And so it went. When he and Trish weren't at the sanitarium visiting Linda—who was practically comatose, thanks to the sedatives her hurtful hubby wanted administered 24/7 on demand—Mr. McMahon made life at World Wrestling Entertainment a veritable Hell on Earth. By late February, even "Daddy's little toy" wasn't safe; the Chairman, betraying his Diva mistress during an Intergender Tag Team Match, joined spiteful daughter Stephanie and William Regal in feeding Trish a mop full of slop, and claimed he was tired of playing with his toy.

Amazingly, Trish begged the boss's forgiveness a week later, and the not-so-magnanimous McMahon accepted—after she completely degraded herself in the ring. Shortly after that, the billionaire sunk even lower by making out with Trish in front of a disgusted SmackDown audience and an incapacitated Linda (whom he decided not to divorce, by the way, lest it should result in her owning 50 percent of everything he ever earned). But as he publicly discussed a "Hollywood Sex Scene" with Trish on Raw the following week, an infuriated Shane McMahon entered the ring to defend his poor mother's honor. Mr. McMahon nervously threw open his arms for a hug; Shane reciprocated with a series of clenched fists, then chased his father and Trish from the arena.

Claiming that his dad's deplorable deeds made him ashamed to carry the family surname, Shane would soon return to the ring with a contract and a question for the dirty old McMahon: "Do you want to play?" With that, he publicly challenged Mr. McMahon to a play-date at the biggest playground in sports-entertainment: WrestleMania X-Seven. Coming out to answer Shane's challenge, the WWE Chairman pointed out that Linda would disapprove of her son challenging his father to a match. He also reminded Shane that he had tested his father when he was 16, then 18, then 24, and he had failed every time. Just as Mr. McMahon signed the contract, his then-son-in-law Triple H attacked Shane from behind, nailing him with the Pedigree. For good measure, Mr. McMahon "sealed the deal" with a chair to Shane's skull, insisting that he would beat his son's ass in a WrestleMania Street Fight, with his debilitated mother watching the carnage from ringside.

Now, a funny thing happened on the way to WrestleMania: a week before the pay-per-view at Houston's sold-out Astrodome, Mr. McMahon announced on Raw that he was acquiring WCW. Simulcasting the news live during WWE and WCW programming, the Chairman boasted throughout the evening that he had officially won the "Monday Night Wars" between the competitive companies (though he had actually done so long before this night), and that he would sign the WCW contract when billionaire Ted Turner himself hand-delivered the paperwork at WrestleMania.

Suddenly, Shane appeared on the TitanTron, which was broadcasting the final WCW from Panama City Beach, Fla., and made a special announcement of his own: "The deal is finalized, and the name on the contract does say ‘McMahon.' However, the contract reads ‘Shane McMahon.' I now own WCW! And Dad, just like WCW kicked your ass in the past, that's exactly what's going to happen to you at WrestleMania!"

Shane would earn the decisive victory at WrestleMania X-Seven's brutal Street Fight—arguably the first time a WWE and WCW representative actively competed in one ring—though he'd have a little support along the way. Former Commissioner Foley invoked a clause that made him the somewhat-biased special guest referee. At one point Trish Stratus helped her billion-dollar boyfriend to his feet, then whacked the tar out of both him and Stephanie, effectively paying back the humiliation she had suffered by their hands. And Linda? Seems she wasn't quite so comatose anymore; in fact, she rose from her wheelchair, scared the crap out of her husband, and launched her foot square into his family jewels. Taking advantage, Shane climbed the turnbuckles and took his father "Coast to Coast," securing the win and ending WWE.com's No. 8 Most Rugged Road to WrestleMania.