She started with the WWE at the age of 13, appearing in catalogues modelling WWE merchandise, whether it be, Hogan-knitted tuques or Rockers inspired t-shirts. It was actually Vince Russo who would come up with the bold idea to have Stephanie join the company as an on-screen character. In the midst of an era that thrived on wacky storylines, Stephanie fit in perfectly as her father was the mastermind behind her abduction from The Undertaker... Yes, wrestling was a different animal back in the day. All would change once Stephanie began to rise in power with Triple H. All of a sudden Vince McMahon’s role lessened while Steph took the on-screen reigns. Today, she continues in her role as one of the most hated authoritative heels in the business. What’s truly surreal however, is the fact that she’s the polar opposite outside of the company.

In this article, we'll look at her sweet and shy beginnings with these 15 pictures. The photos you’ll see in the article include Stephanie as a toddler, working as a merchandise model, a year book photo and a plethora of other pictures where she shows off that shy, billion dollar smile. So without further ado, let’s get to it. Here are 15 must-see photos of Stephanie McMahon before her WWE fame. Enjoy the article and like always, be sure to share it with a friend!

15. Stephanie & Dusty

Early on in her life, Stephanie was spoiled by meeting countless stars of the wrestling business. Although The Dream didn’t stay all that long in the WWE, it was enough for Stephanie to meet the iconic wrestling star. Stephanie was in her early teen years when the picture was taken, while Rhodes endured a lackluster run with the WWE from ’89 to ’91; many call it the worst run of his entire career. Dawning a yellow polka-dotted attire, many believed the gimmick was meant to poke fun at Dusty. He was managed by Sapphire as you see in the picture and his run was the final time he’d wrestle full-time with a promotion.

For the rest of the 90s, he toured from promotion to promotion joining the likes of WCW and ECW. Stephanie and Vince finally welcomed The Dream back with open arms in 2005 and he stayed on board till his final days working down in NXT with Triple H.

14. Family Picture

Not really sure where to begin here. What do you guys think is worse; Vince’s pink/purple shirt, or Shane’s Fresh-Prince wannabe look? It’s a close one, but we’ll give the slight edge to Shane on this one. Anyone else secretly hope he wears the shirt to the ring during his bout against A.J. Styles? What were we talking about again?

Ok, so all jokes aside, this is in fact a nice throwback picture of the McMahon family before Shane and Stephanie would go all in. Shane played a minor role as a referee at one point, while Stephanie had barely any WWE exposure in her childhood aside from working as a merchandise model, which we’ll also take a look at a little later. As for Linda, at that point, she was much more hands-on with the company, even appearing from time to time. Nowadays, she’s pretty much completely out spending her days in the realm of politics working as President Trump’s operator of Small Businesses. Oh, and as for Vince, well, he’s still the same workaholic to this day.

13. A Young Stephanie McMahon

This is a picture of a young looking Stephanie McMahon back in the days when a future in the wrestling business was a distant reality. Steph’s family encouraged her to get educated and she began that pursuit at the Greenwich Country Day School. Following her high school education at the Greenwich High School, Stephanie would further her education at Boston University. In 1998, her studies came to a halt as she graduated with a degree in Communications. Surely, both Linda and Vince must have been proud of their little girl.

Following her graduation, Stephanie would set her sights on the family business which isn’t all that surprising. We’ll discuss her initial role in depth a little later, but it all began with office work out of New York. Shortly after, Vince Russo would pitch the idea to have Stephanie as an on-screen character and like they say, the rest is history as Steph would turn into one of the most villainous characters in WWE history.

12. Daddy’s Little Girl

Since Stephanie was conceived back in September of 1976, it’s been quite clear that she was daddy’s little girl from the start. Looking at the different treatment between son Shane and daughter Steph, some have been led to believe that Vince heavily favors his daughter and son-in-law. That thought process has even played out on-screen, as Vince recently feuded with his very own son.

Whether it’s a work or shoot, the fact remains that the evidence supports Vince’s favoritism over Stephanie. His daughter has a huge role in the company, not only on-screen, but as the Chief Brand Officer as well. Her husband is also high on the WWE totem pole as he readies the future of the company down in NXT. Looking at that, compared to Shane’s minor role as a talent serving as the current Commissioner on SmackDown Live, it’s quite clear to see what Vince is thinking for the future of the business and it looks like it involves Stephanie more than Shane O.

11. Crucified By The Undertaker

Before she broke out as one of the most hated villains on WWE television alongside Triple H, Stephanie was playing a quiet role as the love interest of Test. But before that, she was simply introduced as Vince’s sweet little innocent daughter.

Working at the head office as an accountant and receptionist, Vince Russo encouraged Stephanie to make the transition during a wacky Attitude Era. Vince McMahon never shied away from including his family and he pounced on the idea to make his daughter debut. Her initial cameo was quite creepy as she was stalked by The Undertaker. He would end up capturing and abducting her, leading to Stone Cold playing the role of hero as ‘Taker tried to marry McMahon’s daughter. It was later deemed that Vince was behind the plot, opening the door for the Corporate Ministry. Down the line, Steph would turn on her father, aligning with Triple H and launching her infamous heel character.

10. Steph The New Born

This is a picture of a happy McMahon family during their humble times before the WWE would become a giant monster. Vince is seen in the picture alongside wife Linda, a young looking Shane and newly born Stephanie McMahon.

During the time period that Stephanie was conceived, Vince started to take a major role in his father’s World Wide Wrestling Federation company. McMahon was thriving, earning the company huge amounts of exposure, more so than they ever had before. During that time, Vince also pushed for the company to be renamed to, WWF. Along with that, he had an obsession to promote the brand on a global scale, with that in mind, it was also his idea to set up a match in 1976 (the same year Stephanie was born), between Muhammad Ali and Antonio Inoki.

Shortly after that, by the time Stephanie was six, Vince was getting full ownership of the company, taking it over from his father who was sick at that point. By the age of 37, McMahon was fully in charge of the promotion and would take it to new heights in the 80s during the wrestling boom.

9. Stephanie & Trish

This rare behind the scenes photo shows a young Stephanie McMahon alongside a youthful looking Trish Stratus. Trish would join the WWE in 2000. Although she didn’t have any prior experience in the business, she would rise to fame due to her looks. Back in the 90s, that was pretty much the norm, if fans reacted to a woman, it was probably because she was pretty darn good looking.

The two would end up growing quite close to one another. They feuded early on, which probably brought them so close. The relationship would blossom, and it truly showed just how close the two were when Stephanie inducted Trish into the Hall of Fame. Nowadays, Stephanie is using Trish as the mold for a female WWE Superstar, looking for a talent that has both the looks and in-ring abilities to thrive in the company.

8. Stephanie & Her Protective Brother Shane

Born just in time for the 70s, Shane played the role of the older brother throughout his family life. Shane is six years older than his sister, and was quite protective of her. According to both Shane and Stephanie, Shane O-Mac played to role to a tee. Shane even admitted that he acted like a father towards Stephanie, especially due to the fact that their dad was constantly on the road with the WWE. Shane claims he had a big hand in helping to raise Stephanie throughout her adolescent years.

So one might assume, that Shane wasn’t all that thrilled when it was made public that his little sister was dating a WWE Superstar. Vince made it clear to both that dating someone in the industry was not acceptable. Shane followed the rule marrying Marissa Mazzola, while Steph refused to follow suit. Looking at the tension between Shane and Triple H that still stands to this day, it seems like Shane never got over the ordeal.

7. Year Book Picture

The photo reads: These are the days to hold on to but we won’t although we’ll want to. Thnx to everyone who believed in me. U know who UR Esp Mom Dad Shane AS SK AC.....so on and so on...

The warm and heartfelt message truly gives you an indication of who Stephanie really is away from the camera. She’s a loving and charitable human being, that loves to do good. So many former wrestlers have stated their love for Stephanie claiming she was always there to listen no matter what their concern was. Even the likes of Val Venis discussed how Stephanie would listen to him, when those in creative did not. McMahon would even pitch character ideas to Val, which just shows how invested she truly is in people.

Looking at various real-life backstage pictures, you can see Stephanie’s true bubbly self as she’s all smiles with the likes of Renee Young and heck, even Bray Wyatt. She hasn’t changed all that much from her loveable high school days.

6. Stephanie & Andre

During her youth, Stephanie considered that late mammoth of a man her best friend. Not only was Andre a huge star for the WWE, but he also got along famously with the McMahon family. Stephanie loved hanging around Andre and the picture shows exactly that as the giant’s hand looks to be the size of her entire body. He truly was a surreal specimen standing at 7’4.

Andre helped the WWE reach new heights when the company was peeking during the 80s as Vince took over the company. His rivalry with Hogan put the pro wrestling business on the map and the body slam he took at WrestleMania against Hogan revolutionized the business forever. Some argue, there would be no WrestleMania if not for that epic moment.

Andre would end up leaving the wrestling business for a career as an actor using his acting chops with his mammoth size. Sadly, at the age of 46 he passed away due to heart failure. Stephanie and the WWE continue to honor his legacy today by hosting the Andre The Giant Memorial Battle Royal each year at WrestleMania. They also have a statue of the larger than life wrestler at the WWE HQ. His memory lives on.

5. Another One With Shane

This is another picture of both Stephanie and Shane, with Shane rocking the baseball inspired shirt, a look he still sports today for matches. Seems like some things just never change.

For Shane, his WWE involvement began long before Stephanie. He would debut as a ref named Shane Stevens. He participated in such events wearing the stripes like 1989’s Survivor Series, WrestleMania VI and ’91 Royal Rumble. He would change his role to something more behind the scenes as he was spotted backstage at WM VIII, breaking up a brawl that featured two icons of the business, Randy Savage and Ric Flair.

Like Stephanie, during the Attitude Era his on-screen role would increase joining forces with the likes of The Corporation and The Corporate Ministry. He stayed on board till October of 2009 when he decided to leave the company and make a living elsewhere. Shane returned seven years later in February of 2016 to a thunderous ovation. He hasn’t left since.

4. Steph The Merchandise Model

Rocking the Hulk Hogan knitted winter hat, Stephanie’s first WWE exposure was as a merchandise model for the company. Stephanie rocked several wrestler inspired outfits including this Hulk Hogan hat which surely was a best seller at one point. Hogan took the WWE by storm in the 80s as he changed the wrestling business forever. Vince was fully invested in the Hulkamania character and it led to some big time results. It wasn’t till Hogan left that the WWE started to fall.

As the Chief Branding Officer, Stephanie is in charge of reeling in the sponsorship deals. With that said, the WWE needs to have a clean identity in order to please those that want to invest in the company. After his racist rant, Hogan became a liability to the WWE and was instantly let go, obviously, because of a PR move. Without a doubt, once all the dust settles, Stephanie and Vince will welcome Hogan back to the company.

3. More Merchandise

Yup, we needed to add more merchandise photo from Stephanie’s earlier days as she rocks a couple of tees from popular WWE stars of the early 90s. The bulldog t-shirt represents the British Bulldogs which was made up of the late Davey Boy Smith, Dynamite Kid and of course, the star of the act, Matilda, the dog.

The other shirt Stephanie is rocking is of The Rockers Tag Team, which featured Marty Jannetty and Shawn Michaels. The two enjoyed big time popularity and were regarded as an exciting trailblazing act which emphasized speed, agility and overall in-ring skill. Something the WWE would turn to during the mid 90s. As for their career trajectories, Michaels would become the face of the company and arguably the greatest wrestler that ever lived, while Marty, became an afterthought who continues to spiral nowadays still attending indie wrestling events competing as performer.

2. A Great Family Picture

This is a great family picture featuring Stephanie and her fam, along with her sister-in-law, Shane’s wife, Marissa Mazzola. The couple tied the knot over two decades ago way back in 1996. Shane and his wife share three sons, the opposite of Stephanie and Hunter who have three daughters. Mazzola-McMahon also worked for the WWE at one point in time serving as an on-screen co-host for the show LiveWire. Remember that recap show? Who can forget Michael Cole rocking those awful turtlenecks while telling us about things we already saw...

Interestingly enough, Mazzola previously worked in a similar role to Stephanie as she was in charge of overseeing public relations. Marissa was the Executive Vice President of Global Media for the WWE.

Unlike Stephanie and the other McMahons, Mazzola would not partake in an on-screen role at any point. She was recently spotted on WWE television as she was ringside during Shane’s WrestleMania return bout against The Undertaker.

1. Billion Dollar Smile

For the number one throwback picture, we felt the need to show Stephanie in all her glory as she shows us that million dollar smile, one that she still maintains today. Remarkable to see her growth in the company, Steph began in sales at the WWE head office and would also work as a receptionist. She served as an Accountant Executive for the company at one point, but that would all change once she stepped foot in the ring.

Her contributions would continue to blossom from then on working as a Director for Creative, Senior Vice-President of Creative, Executive Vice-President of Creative Development and Operations and of course, her current role: expanding the company as the Chief Brand officer.

With all those titles, Stephanie has also been crucial to the on-screen product while even raising a family. Not to mention her role in revolutionizing the Women’s Division. She’s come a long way from that shy girl with the innocent smile.

Sources: YouTube, WWE