Stephanie McMahon is a woman of many skills and talents. A wrestler by nature, Stephanie also dabbles in bodybuilding, modeling, and maintaining her family business. It’s why she’s entrusted with the title of CBO. Along with her husband and father, Stephanie is what makes the WWE tick. They keep it alive and task themselves with giving the fans what they want. That shouldn’t be too hard for Stephanie to figure out as she’s been in the business practically all of her life. While she’s been on the Tail end of some hate, Stephanie’s done some good things for the WWE as a whole. As we go forward, it’s her and her husband who will guide the company into the future. But before that let’s go back in time.
It wouldn’t be too farfetched to say that wrestling fans have watched Stephanie grow up. We’ve seen her come in the business as a wide-eyed young woman and watched every mistake, embarrassment and success that the professional arena has thrown her way. From her demeanor to her appearance and her skills as a wrestler, much has changed since she debuted all the way back in 1999. A lot has happened since then and there’s most definitely more to come. But until then let’s look on back at some of those moments in Stephanie’s youth.
20 On The Ropes
Stephanie has always had a talent for riling up audiences. Whether they’re cheering her on or booing her feverishly, the woman knows has to get a reaction out of people. That’s not all too surprising considering who her father is. Still, Stephanie has come a long way since she first took stage. She’s matured both in and out of the ring and has become synonymous with the WWE brand. It’s hard to believe that she was once a novice at working the microphone. This picture shows Stephanie in her younger years presumably talking to the crowd. While it’s hard to pinpoint exactly when and where this was taken, she looks like she’s got the hang of it.
19 The Undertaker’s Bride-To-Be
Stephanie came into the business at a time where it wasn’t uncommon for women to take a backseat to male talent on the roster. As such, it wasn’t at all unusual to see them thrust into romantic storylines in order to get them over. However this wasn’t the traditional romantic subplot fans would grow used to seeing on WWE programming. TUndertaker and Stephanie’s ”Dark Wedding” was one of the more disturbing segments in WWE history. The kidnapping and near forced wedlock of the young McMahon certainly drew a lot of attention and still holds up all these years later. But as you can see in the picture above, the whole thing resembled a Salem witch hunt more than an actual matrimony. Well, that was probably the point though, wasn’t it?
18 Mom and Daughter
Behind all the kayfabe, celebrity and responsibility that comes with owning the biggest wrestling promotion in the world, the McMahon’s are a family first and foremost. We’ve seen them quarrel viciously in the ring – sometimes even getting physical – but we know that it’s all for show. What we don’t see as often are things like this. These tender moments captured on camera that show how tight they are as a unit. As the family continues to grow, we’ll no doubt see some more McMahon’s added to the WWE roster. In this picture we see a young Stephanie and Linda together. Stephanie looks like she’s pretty young in this one. We’d guess this was taken some few years before her WWE debut.
17 The Wedding
There are a few wedding pictures on this list, so bare with us here. This one however has the distinction of being the real deal. You can tell by the general lack of a stage, post, large crowd ect...This wedding occurred four years after Triple H and Stephanie’s made for TV matrimony, in 2003. They were a couple for so long that their on screen personas had already gone through a handful of marital problems by the time they really did end up tying the knot. All that aside, this is a terrific picture of what’s been a lasting marriage. All the success in the world and three kids later, these two are still as compatible as they were in their youths.
16 Spanking Trish
Here’s more than a little bit of fan service for you guys. The WWE is full of beautiful women, Stephanie included. Time after time, writers find ways for these beautiful girls to show off their skills and strut their stuff. Of course, Stephanie is no exception and thankfully didn’t inherit any of her father’s rough features. No Way Out 2001 saw Stephanie partake in one of the steamiest moments of her career. Amidst the drama surrounding her family throughout the Trish Stratus – Vince McMahon romance, Stephanie took the future seven-time Women’s Champion to school. What culminated was this jaw dropping scene you have before you.
Well it was bound to rear its head eventually. So long as we’re looking back on Stephanie’s younger years, we might as well go over one of her bolder ideas. Though it certainly isn’t reflective of the sport as a whole, professional wrestling is something of a looks-driven industry. Most of its stars are pretty easy on the eyes. That rings especially true for the female talent. Stephanie is no exception to this and while she looked perfectly fine as she was, somewhere along the way she decided it was time for an “enhancement” if you will. While she certainly showed that she had the talent to make a name for herself, she also went after the look and all the more power to her for it.
We’ve always known Stephanie as a dark-haired beauty. For over a decade WWE fans have gotten used to that kind of look on her and it’s often these small details that we come to associate people’s images with. But for a time, Stephanie tried going blonde and you’ve got to admit, she looked great. Though not as iconic as other WWE Blonde’s like Stacy Keibler and Trish Stratus, Stephanie held her own. The lighter shade rejuvenated her look, making her look younger than she already was at the time of this picture. As always, Stephanie looks to be the center of attention in this picture, taking control and showcasing her skills on the mic. You know the new hairdo helped her out in that regard.
13 Booty Call
This is probably one of the more salacious moments captured on our list. We all do things we’re not proud of when we’re young, and Stephanie McMahon is no exception to that. Though there have been numerous questionable WWE storylines over the years, at least this one finds itself as one of the tamer one’s if you can believe it. John Cena – operating under his “Doctor of Thuganomics” moniker – started the whole thing off by asking Stephanie if he could give her a little smack. Stephanie responded by taking it a step further, bending over and daring him to follow through. Not something you’d want your kids to see, that’s for sure.
12 Stephanie Claus
Christmas is a time of laughter. A time where family and friends gather together and celebrate the joys of giving – and in this picture, Stephanie sure gave the WWE Universe a lot to be happy about. No one can say that the WWE doesn’t give anything to its fans. There was a time when Stephanie was atop every wrestling fans wish list, and this picture here gives us a peek into that time. The red top and Santa hat are a nice touch. They really sell the getup as a whole. Though Stephanie doesn’t look like she’s got the holiday spirit, we’re sure her Christmas turned out just fine.
11 WrestleMania X8
WrestleMania is a platform for many wrestlers to achieve a lifelong dream and gain recognition they’ve put their whole lives towards earning. It can make someone’s career or leave them reeling towards unfulfillment on a grand scale. While most people use their skills and wrestling ability to stand out on this platform, someone as well known as the CEO’s daughter doesn’t need to prove much. So then, how do you make an impact? Well you’re attire obviously. Accompanying Chris Jericho to the ring, Stephanie certainly stole her fair share of glances that night. Her teal skin-tight jumper certainly aided in making everyone’s night that much better, that much is sure.
10 Howard Stern Show Interview
The Howard Stern Show gained a reputation as one of the more risqué programs of its time. Nothing was really off limits when you got down to it and anything and everything could and seemingly would be brought up. From guest to guest, Stern managed to get the absolute best out of his guests. So what happened when the WWE’s heir apparent Stephanie McMahon showed up on the show? Well, it was much of what you’d expect from the program. In other words, nothing all too surprising for fans of the show. The typical sleazy and bawdy conversations took place, with the young McMahon even talking about some very intimate issues.
9 ECW Owner
The biker-ish look seems to compliment Stephanie nicely in our next picture. While she goes for a more businesswoman-like wardrobe nowadays there were times in her youth when she’d try out some more liberal clothing. This is certainly one of those instances. Of course, wrestling fans will recall the failed Invasion storyline and the major disappointment that followed whenever they hear the words Stephanie McMahon and ECW in the same sentence. Though only an owner in name, Stephanie filled in the role nicely. While it was only for a short time, Stephanie was definitely suited for the role. She takes control easily and she’s showed that in abundance during the last several years.
Regardless of when you started to follow wrestling, you’d have to have at least taken notice of the early years of Stephanie McMahon. We might be most accustomed with her current iteration in the WWE but she’s gone through a number of changes and matured immensely as a wrestler and person over the years. There was a time where this now intimidating woman was known less for her abrasive personality and more for her position as the “Billionaire Princess”. When you look at pictures of Stephanie in her youth, it’s easy to see why people underestimated her. She was incredibly charming as a young woman. She didn’t need to be able to work the mic or hold her own in the ring (not that she couldn’t) because she was just that captivating.
Halloween’s a great time for people to cut loose and mess around, dressing up, partying with friends and getting in some harmless fun. It’s also an opportunity to dress in a somewhat more sultry way than usual. This picture was taken when Stephanie was the SmackDown General Manager and Eric Bischoff was the Raw GM. The witch costume Stephanie chose is certainly fitting. And you’d be lying if you denied taking at least a few good looks at her that night. However this busty attire wasn’t even the most jaw dropping thing that happened that night. That definitely has to be Bischoff sneaking into the SmackDown locker room and stealing a kiss from the young McMahon.
6 Wedding With Test
It’s a little weird to see Stephanie with anyone other than Triple H at this point in time. But let’s not forget that the two weren’t always an item. In fact, Stephanie entered the WWE with another chum. Her first WWE relationship was not with her eventual husband. As all you remember, Test was pegged to be Stephanie’s main man early on in her career. This is entirely fictional of course but still strange to think about. Perhaps not as strange as the storyline that surrounded their relationship, with kidnapping, drugs and shady Vegas drive in nuptials all on the table. Still not the weirdest thing WWE’s done, but given that this is the boss’ daughter we’re talking about it’s up there.
5 Armageddon 1999
Speaking of the Stephanie and Test relationship, let’s turn our attention to this image up here in which we see the future heads of the WWE in their early years as a power couple. Just before the turn of the century wrestling fans witnessed what would be the formation of what would be the most powerful duo in the industry for the next decade-and-a-half. As the whole strangeness attached to her faux wedding to Test resolved, Stephanie found herself in the middle of a No Holds Barred match between Triple H and her father. Well, she ended up in the winner’s corner but it was the wrong corner all together. At least that’s what it seemed like as Stephanie betrayed her father for the first time, propelling herself and kickstarting a new era in the process.
4 Blue Top
There’s not much history to discuss in this photo. As opposed to the last few images we’ve gone over, there’s not all too much going on in this picture. No wrestling, no promo, no candid family pictures. Just Stephanie in a nice blue top. While there might not be all that much going on within the picture, Stephanie’s expression says it all. Her look, her posture and that little pout she’s put on make it abundantly clear. There’s a reason they call her the “Billion Dollar Princess”. She gets what she wants, when she wants it and regardless of what she has to do to get it. A lot has changed over the years but that sure hasn’t one bit.
3 Women’s Champ
Say what you will about Stephanie McMahon, but she hasn’t gotten where she is by sitting around and looking pretty. She’s earned her fair share of the pie. Like most other sports, people judge wrestlers on their achievements. You can be a fan favourite and have some solid skills in the ring, but nothing speaks louder than getting some hardware to put on display. As a onetime Women’s Champion, Stephanie has her bases covered in that regard. Winning the title back in 2000, Stephanie – whose career was still on the rise – squared off against Jacqueline and unsurprisingly claimed the title. She held onto it for a decent amount of time before Lita relieved her of her duties.
2 SmackDown GM
It’s not uncommon for the modern wrestling fan to view Stephanie McMahon as an authority figure within the WWE. While she got her humble beginnings at the bottom of the pecking order, Stephanie quickly – and somewhat predictably – shot up the ranks. You could try and dissuade it all with talk of her Father pulling the strings for her and things like that, but regardless of how she’s gotten an opportunity Stephanie has always performed admirably. This is a throwback to her days as SmackDown GM. The promo involves the return of the Undertaker and some mentioning of a big surprise for fans. But something tells us that the fans were cheering for an entirely different reason that night.
Like we said, Stephanie is often perceived as an authoritative figure within the WWE. Now more than ever. But it seems that in her youth she found herself in several positions of authority, seemingly grooming her, preparing her to take the reins. Not only was she usually convincing, but she often looked damn good doing it. The special guest referee was a chance for wrestling fans to see their favorite Divas take on more of an authoritarian role. Stephanie took on the role at No Way Out 2002, overseeing a match between Kurt Angle and Triple H. While the match itself was a pretty big draw, nothing could’ve prepared audience for the sight of Stephanie McMahon in a referee uniform. The stripes, the shorts, the hair – everything about it was fantastic.