Some might say that Stephanie got her start with WWE at the age of 11, serving as a model for the WWE catalog merchandise section. She started at the head offices over in New York following her university bachelor’s degree. Her first gig came as a receptionist and accountant. However, her true calling came on-screen, in late ’99, Stephanie would turn into the biggest villain and that would carry into the 2000s as she got better and better in the role.

Nowadays, things have changed for Stephanie. She’s in a corporate position as the brand ambassador. When Vince decides to relinquish control, Stephanie has to be the next in line to run the company.

For now, let’s take a look at some of her candids from both then and now. Stephanie wasn’t ready for these pics, which makes them that much more entertaining. Enjoy folks, let’s get started.

Stephanie McMahon 1st Titantron

One-on-Ones – Stephanie McMahon

Stephanie McMahon Top 10 photos paparazzi Real Life

13Candid Ambassador Work

Stephanie McMahon speech
via Pinterest

Stephanie has a great way of connecting with those that she meets. Take a look at her history working alongside talent and rarely does anyone have anything bad to say pertaining the McMahon.

A position as the brand ambassador way a no-brainer. Stephanie takes part in lots of talks around the world – however, she’s not always ready for a pic, like in this candid photo. Of course, ready or not, she looks like a true beauty.

12New York Candid

This rare throwback shows Stephanie McMahon during her rise to fame in 2000, outside of WWE New York. Originally, Stephanie also worked out of the head offices in New York, serving as a receptionist and account executive.

The photo shows Stephanie arriving and leaving – even when she was a big villain for the company, she always made time for the fans, signing autographs and sporting a big smile.

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11WrestleMania X-8 Press Conference

Stephanie McMahon WM X-8 press conference
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The photo above shows Stephanie’s prime run as a heel, on the road to WrestleMania X-8, aligning herself alongside Chris Jericho.

Stephanie would be repackaged shortly after, turning into a babyface General Manager over on SmackDown. For what it is worth, the rare Stephanie shot is selling on eBay at the moment.

10Kissing Shane

Stephanie McMahon and Shane
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Despite their differences on television, Shane and Stephanie have always kept a close relationship. When Vince was constantly on the road during Stephanie’s upbringing, Shane served as Stephanie’s protector.

We get a rare shot of the two embracing one another back in the early 2000s. Both have changed since the photo – as well as their status with the company.

9Throwback With Rourke

Stephanie McMahon and Mickey Rourke
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We get a glimpse of the real Stephanie McMahon in the shot above. That smile from ear-to-ear, that shows who the real Stephanie is, outside of her heel on-screen character.

Mickey Rourke is also present in the photo – he would make a cameo at WrestleMania, though most fans wanted to see him in an actual match against Chris Jericho. Fans had to settle for a brief skit between the two that ended with Mickey getting the last laugh.

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8Candid With Mom

Stephanie McMahon and Linda
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This time we have a candid featuring both Lina McMahon and Stephanie. Both are part of a speaking engagement in the candid photo.

The two have a storied history in the ring as well, Stephanie calls the moment of slapping her mom the hardest of her entire career. She had a lot of regret after the moment went down – it was the ultimate heel move for someone that is a kind-hearted babyface in real-life.

7Signing For The Fans

Stephanie McMahon autographs
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This is the side of Stephanie we don’t see, traveling like the rest of us – the only difference, she has to deal with lots of fans.

TMZ stopped McMahon asking her some questions. At the same time, she was signing autographs for fans that came more than prepared. One guy had a rare Stephanie action-figure ready to sign. The class act that she is, Stephanie signed it without hesitation.

6Wedding Candid

Stephanie McMahon wedding
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In 2003, Stephanie went from losing a match to her own father one week and getting written of storylines, to marrying Triple H the very next week, as her father walked her down the aisle. Now that’s the McMahons for you!

It was the start of a lengthy hiatus for Stephanie, she would appear sporadically from then on, starting a family during the time period.

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5Ready For Mania

Stephanie McMahon bike rehearsal
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The work that goes into WrestleMania can give anyone anxiety. It goes very in-depth and that includes entrance rehearsals. For Stephanie and Triple H, that meant getting adjusted to their motorcycle rides.

We get a rare glimpse of the two revving them up in the parking lot. As a birthday gift, Triple H bought Stephanie the same motorcycle from the show.

4Backstage Candid

Stephanie McMahon backstage throwback
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A backstage candid taken of Stephanie during her run as the GM of SmackDown. At this point, Stephanie was branching off backstage as well, serving as the head of creative.

It was at that point when Hollywood writers slowly started entering the mix, replacing the old school booker type mentality. This was a move fans really weren’t too fond of.

3Pregnant Stephanie

Stephanie McMahon pregnant candid
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Without a doubt, Stephanie did not want to be featured in this candid throwback shot as she looks very pregnant in the background and in a bit of distress.

Hunter looks stressed out himself and to add to the situation, he’s forced to pose for this hilarious picture. Credit to Hunter for still accepting the photo request.

2Candid Street Pose

Stephanie McMahon candid
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Even when she’s caught off guard during an appearance, Stephanie shines through in the photo.

Nowadays, McMahon is doing most of her work off-camera over at Stamford at the WWE HQ. During these tough times, Stephanie is putting in lots of work back at home, educating her children as they continue to be off school given the current circumstances.

1Group Candid

Stephanie McMahon Undertaker Triple H and Sara
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A rare throwback for the ages, featuring a young Stephanie McMahon alongside Triple H, The Rock, The Undertaker, and the Deadman’s ex-wife, Sara. It was said that Sara was very overprotective backstage, threatening anyone that got close to her man. Yea, that relationship did not last, ultimately.

This picture is an iconic one, to say the least – showing the trio without their gimmicks and pretty much like the rest of us.

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