10 Things People Should Know About Stephanie McMahon's WWE Rookie Year In 1999
Stephanie McMahon joining the WWE roster in 1999 showed how much Vince McMahon was committing to writing angles for his family. The soap opera style WWE adopted in the Attitude Era placed Vince’s children at the forefront. Shane at least spent years working in various roles, but Stephanie was thrown into the fire at just 23 years old with no acting experience.
Quite a few things get overlooked from Stephanie’s time in WWE during that first year. Major names worked with Stephanie and witnessed her eventually swimming in a sink-or-swim scenario. Vince was dead set on having his kids add to his storylines. Stephanie McMahon had the following things coming into play in her rookie year for WWE.
10 Vince Russo Pitched Using Her On TV
It is kind of funny that Vince Russo was originally the person who suggested Vince McMahon consider having Stephanie McMahon become an on-screen character. Stephanie ended up playing a huge role in Russo not coming back when almost signing in 2002.
However, Russo loved the soap opera-style storylines and had a lot of sway in 1999. McMahon ended up agreeing to Russo’s idea and had his daughter joining the product after Shane got over as a heel the previous year.
9 The Undertaker Was The First Person To Reference Her
WWE booked a strange feud between The Undertaker and Vince McMahon with vague references to Vince’s family. This started when Vince was still a heel feuding with Steve Austin, so the evil Undertaker making threats to him felt out of place.
Austin beating The Rock and getting past McMahon’s hurdles allowed the program with Undertaker to start playing out. Stephanie was referenced by Undertaker to show he could get into Vince’s head and eventually abducted her in her first storyline.
8 Test Had To Defeat Shane McMahon To Date Her
The second storyline for Stephanie McMahon came after the whole drama with The Undertaker ended. WWE found a more traditional angle to have Stephanie do more than be a damsel in distress. Newcomer Test had a lot of expectations from WWE and was placed in an angle dating her.
However, the story evolved into Shane attacking Test and trying to stop the wrestler from dating his sister. SummerSlam 1999 featured an underrated Greenwich Street Fight with Test defeating Shane and Shane having to accept it as part of the stipulation.
7 Only Wrestled One Match Defeating Jeff Jarrett & Debra
Shane McMahon started wrestling a few matches in 1999 when he was respectable as a newcomer in the ring. Stephanie McMahon was never a wrestler as much as Shane, but she eventually did some matches once turning heel.
The only match to come for Stephanie in her rookie year was a mixed tag with Test against the duo of Jeff Jarrett and Debra. Stephanie pinned Jarrett for a hilarious moment that featured little in-ring action since she wasn’t ready for that.
6 Mae Young & Moolah Were Part Of Her Bachelorette Party
The infamous segment of Triple H drugging Stephanie McMahon and marrying her came at the end of her bachelorette party. WWE aired segments of the party all night of the wedding since it took place in previous days and was filmed.
The Fabulous Moolah and Mae Young were part of Stephanie’s wedding party. WWE loved using them in comedy segments with Young making Stephanie’s party rowdier than she expected. This opened the chance for Triple H to put his plan into action with Stephanie distracted.
5 Her Wedding Segment Main Evented Raw
WWE had a few wedding segments before Stephanie McMahon and Test, but they had the golden spot of main eventing Raw. Triple H revealing the video footage of him marrying Stephanie in a drive-through chapel was a huge moment that had to close the show.
The feud between Triple H and Vince McMahon reached a heated enough point that Triple H not only ruined her wedding but married her. Vince’s anger while Stephanie cried closed the show to set up the next few weeks of storytelling.
4 Conned Vince McMahon With Triple H
Armageddon 1999 featured Vince McMahon having his biggest match since his feud with Steve Austin ended. The dynamic was new with Vince now playing a face character standing up for his daughter in a match against Triple H.
However, it was the ending that everyone remembers when Stephanie embraced Triple H to reveal they were in on the plan all along. Triple H winning the match and having Stephanie as his new love interest made him feel like a much bigger deal.
3 Used Callback To Higher Power Angle To Explain Heel Turn
WWE set up this huge storyline swerve by using a previous swerve as part of the payoff. Vince McMahon instructed The Undertaker to abduct Stephanie McMahon when revealed as the Higher Power wanting to screw Steve Austin at any expense.
Even though Vince was now a face, Stephanie was in the right when she wanted revenge for her father manipulating her like that. The rationale was that Stephanie found the best way to get revenge by marrying his most hated enemy for a heel turn.
2 Became A Member Of D-Generation X
The end of 1999 saw D-Generation X reuniting when X-Pac and the New Age Outlaws started doing Triple H’s bidding again. Stephanie McMahon becoming the love interest of Triple H placed her into the group by proxy.
2000 started with Stephanie and Tori becoming the female members of the group and adding a fun dynamic. Triple H’s career started to reach new heights with his popular faction back and starting a heel power couple with Stephanie at the same time.
1 No Pay Off To Betraying Test
One of the strangest things about Stephanie McMahon’s rookie year in WWE was how her relationship with Test ended. The couple dated for months and had an engagement end when Triple H ruined the wedding, but Stephanie was clearly part of that plan.
However, Test never got to have any real revenge, nor did he interact much with Stephanie or Triple H. There were some moments of the evil couple using their power to put him in tough matches. Unfortunately, Test never even got to have a PPV match with Triple H to pay off his heartbreak.
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