Stephanie McMahon’s five greatest WWE moments

By Ryan Satin
FOX Sports WWE Analyst 

Stephanie McMahon is one of WWE’s most well-known characters. 

Starting in the 1990s as an innocent, young lady dragged into a storyline involving The Undertaker and her father, Vince McMahon, Stephanie would grow to become a force on WWE TV in the decades that followed.

With the “The Billion Dollar Princess” announcing last week that she’d be taking a leave of absence, now felt like a good time to take a trip down memory lane and reflect on her five greatest WWE moments.

5. The Unholy Wedding — April 26, 1999

This was Stephanie McMahon’s first big story in WWE.

After being “abducted” at Backlash, The Undertaker offered to return her safely the next night on Raw in exchange for control of the entire company. Vince obliged and said he’d meet at an agreed upon location.

When Vince arrived, Undertaker revealed he was still at the arena for an “Unholy Wedding” with McMahon’s daughter. Classic goth, villain-move. 

Thankfully, “Stone Cold” Steve Austin intervened, and the creepy nuptials were never finalized — but the whole thing will forever be thought of as one of Stephanie’s most memorable on-screen moments.

4. Wedding with Test — November 29, 1999 

This one hasn’t necessarily aged well over time, but it’s part of the foundation of Stephanie’s on-screen character.

After the whole Undertaker cross situation — sorry, not a cross, a symbol — Stephanie would later transition into an on-screen role dating wrestler Test. The two would eventually become engaged and the wedding was set for an episode of Raw.

Unfortunately, Triple H interrupted the ceremony to reveal he had eloped with Steph the night before at a drive-thru wedding chapel in Las Vegas (while she was unconscious). 

I told you this one didn’t age well!

Stephanie cried angrily realizing her dream wedding had been ruined, Vince McMahon cursed Triple H from the ring, and the crowd went bananas.

It was a dramatic, yet unforgettable scene.

3. Brie Bella match at SummerSlam — August 17, 2014

Following the first Father vs. Daughter, No-Holds “I Quit” match in 2003 against Mr. McMahon, Stephanie took a lengthy hiatus from in-ring competition.

In that time, the former WWE Women’s champ still made appearances on TV, but for ten years, she stayed away from an actual match.

That is until 2014 at the height of the “Yes! Movement,” when The Authority’s issues with Daniel Bryan led to a match against his wife Brie Bella.

While this might not have been a technical classic, the match proved Stephanie still had something left in the tank and could perform once more for a new generation (without looking out of place). 

Plus, that arrest angle was classic.

2. Stephanie and Triple H vs. Ronda Rousey and Kurt Angle at WrestleMania — April 8, 2018

For as long as Steph was an on-screen character in WWE, she surprisingly only competed in one WrestleMania match herself.

“The Billion Dollar Princess” made it count, though, by teaming up with her husband against Ronda Rousey and Kurt Angle in match that allowed the current SmackDown Women’s champ to debut in a big way. 

As of now, this was Stephanie’s final match in the company, and if that ends up being the case forever, it was an entertaining swan song.

1. Turning heel on Vince at Armageddon — December 12, 1999

Kicking off WWE’s infamous McMahon-Helmsley era by turning heel on Mr. McMahon, of all people, has to be Stephanie’s greatest hit.

Circling back to the “Unholy wedding” with Undertaker, Vince would later admit he was behind the whole thing just to mess with “Stone Cold.” 

No, he did not clue his daughter in beforehand, and she was pissed.

So angry, in fact, that she made amends with Triple H for marrying her while unconscious and decided to actually be in a relationship with the guy.

This caused her to betray Vince in a match, join up with Triple H, and ultimately become the top duo in all of WWE, leading to a reign of terror that would be felt by babyfaces for decades to come.

Do you agree with these picks? Hit me up on Twitter @RyanSatin and share your take!

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Ryan Satin is a WWE analyst for FOX Sports. Satin previously appeared on FS1’s “WWE Backstage” and founded Pro Wrestling Sheet, where he broke countless news stories as editor-in-chief.