Punching Shawn Michaels' wife and 3 other evil WWE moments from SummerSlam history

As the second most important event of the year, SummerSlam is one of WWE's most memorable spectacles. The Biggest Party of the Summer has had many highlight-worthy moments.

From Brock Lesnar's decimation of John Cena to Evolution's betrayal of Randy Orton, fans have witnessed legitimate shockers at the event. However, there were a few instances where the WWE Universe was left with their jaws dropped.

On that note, let's look at the four most evil WWE moments from SummerSlam history.

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#4 The Fiend leads WWE into a new era of darkness (SummerSlam 2019)

The Fiend cast an enormous shadow of darkness in his debut encounter.

Post-WrestleMania 35, the returning Bray Wyatt expressed a conflicted personality centered around two characters, a jovial TV show host and a sadistic monster with a hideous mask.

Although we received a few glimpses of The Fiend, Wyatt's alter-ego, the WWE Universe got the first real taste of the monster at The Biggest Party of the Summer, where he battled Finn Balor in Toronto.

From the get-go of the entire segment, the fans were enthralled and appalled. Wyatt came out to a modified version of his previous theme song amid a fascinating and awe-inspiring theatrical display.

The fun ended quickly, especially for Balor, as The Fiend obliterated his foe despite the offense his opponent mounted. The vicious Mandible Claw was enough to put the first-ever Universal Champion away.

The beauty of The Fiend's debut was that it quickly introduced the fan base to one of the most ominous characters in wrestling history, perhaps on the level of The Undertaker.

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#3 The Undertaker Chokeslams Edge to "hell" (SummerSlam 2008)

The Undertaker vs. Edge is one of SmackDown's most memorable rivalries. This historic narrative had everything from marriages to "Edgeheads" to divorces, culminating in the most fitting way possible.

After a falling out with her on-screen husband, Edge, SmackDown General Manager Vickie Guerrero rehired Taker and booked The Rated-R Superstar against The Phenom inside Hell in a Cell.

Taker bested Edge inside the satanic structure in the war pursued at SummerSlam 2008. However, the match is remembered for its immediate aftermath.

The Phenom chokeslammed his rival from atop the ladder through the ring canvas before setting ablaze the ring. For a rivalry that spanned a year and pushed Taker to the limit, this was the most "feel-good" conclusion that WWE could have booked.

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#2 Chris Jericho punches Shawn Michaels' wife (SummerSlam 2008)

Hardcore wrestling fans will recall Chris Jericho's criminally underrated rivalry with Shawn Michaels in 2008, which piqued at The Biggest Party of The Summer.

HBK and his wife, Rebecca, entered the ring to announce his "retirement." This came after Jericho threw the four-time world champion through the Jeritron on The Highlight Reel. The speech was going well until the current AEW star confronted him.

When Michaels insinuated that Jericho would never be as good as him, things descended into pure chaos. This prompted Y2J to throw fists. However, HBK ducked, and the former AEW World Champion accidentally touched Rebecca's face, legitimately injuring her.

Albeit unintentional, this was the turning point of this memorable feud as tensions escalated beyond measure, and fans began to wonder if there was legitimate heat between the involved parties.

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#1 Brock Lesnar leaves Randy Orton in a pool of blood (SummerSlam 2016)

Often, professional wrestling can become more gruesome and "real" than mixed martial arts or any other sport. This was especially true during the climax of SummerSlam 2016, which had one of the most shocking endings imaginable.

WWE had advertised a blockbuster dream match between Randy Orton and Brock Lesnar. Since both men were on opposite brands, the encounter became a matter of brand warfare.

As for the match itself, it was pretty underwhelming in light of the sky-high expectations. Both men executed their finishers with little success, but the dramatic ending was completely unexpected.

Lesnar removed his gloves and punched away at Orton, legitimately busting open The Viper. The 14-time world champion was concussed too. Shane McMahon came out to restore order but received an F5.

Hostility grew backstage when Lesnar got into a heated argument with Chris Jericho, who was concerned for Orton's health.