Stephanie McMahon Then Vs Now: Which Do You Prefer?

Making her WWE on-screen debut in the late 90s, nobody could have predicted Stephanie McMahon would become one of the greatest non-wrestling heels in company history. After all, thinking something of the sort was preposterous given her real-life persona as a shy and genuine human being. As they say, the nicest people make the greatest heels and that’s exactly what took place with Stephanie who took her character work to another level in the early 2000s. Today, she’s taken things a step further as the Brand Ambassador and Commissioner of Raw (although she’s been MIA on screen since early April).

One constant throughout her persona changes is her look. Whether it was in 2003 or 14 years later in 2017, McMahon still takes are breaths away with those fantastic “assets”. In this article, we do the impossible matching up the Stephanie of “then” against the Stephanie of “now”. From her run as SD GM back in the day to her public appearances in the now era, we’ve got it all in this article so brace yourselves. We ask Sportster Nation to let us know via Facebook which Stephanie do you find hotter. It’s one hell of a tossup!

Enjoy the article and like always, be sure to share it with a friend. Here are a slew of pictures featuring Stephanie McMahon of THEN versus NOW: Which “assets” do you prefer? Let’s get started!

15 Then – Steph’s Prime


We start the article off with a straight punch to the stomach to the current Stephanie McMahon with this mouth-watering throwback picture. If Steph was in a boxing fight against her current self, let’s just say she just landed a solid blow in the first round with this picture, my oh my!

According to the world wide web, this was Stephanie’s absolute prime in terms of physical features or what we here on The Sportster like to refer as “assets”. The year was 2003 and Stephanie was reaching the tail end of her run as the General Manager of SmackDown. Her final piece of work would come against her father, she departed after her ’03 No Mercy match and would return sporadically from 2005 to 2007. Leaving with such a look as you see in the picture above, she was truly missed at the time of her departure.

14 Now – Rare “Not So PG” GM Attire


The modern day Stephanie McMahon is quite different to the Stephanie of “then”. Nowadays, her attire choices seem to be fitting with the WWE’s direction of becoming a PG company. Her outfits have followed, however, many argue the heat voltage meter never went down. Rocking some of the tightest dresses, even today Steph maintains smokebomb status.

The picture above however was a rare glimpse of Stephanie rocking some serious cleavage, fans ogled at the attire given the fact that it’s so rare to see Steph and a “Not So PG” outfit nowadays. Truly doesn’t get better than this picture as Stephanie power walks to the ring, with the blazer and revealing top, oh if only she ditched the blazer... We’ll take what we can get, and this attire truly rivals the previous entry on this list.

13 Then – In-Ring Attire


We can hear The Sportster crowd chanting “holy s***, holy s***”. We seriously don’t blame you as once again, the Stephanie from the past dazzles with a terrific outfit, this one was actually meant to be for an in-ring match. Ohhh the good ol’ days!

Steph’s in-ring involvement was certainly nothing spectacular, however, it was an attraction that’s for sure. She took part in some notable encounters back in the day including a championship run as the Women’s Title holder, something the WWE rarely acknowledges cause like, it was pretty wacky giving a belt to someone who couldn’t wrestle. She took part in a couple of other encounters usually drawing even more heat from the crowd. However, rocking the outfit you see above, she drew a different kind of heat on this night...

12 Now - Recent Instagram Post


For the now portion, we wanted to find something very recent for this entry, and with Stephanie on the sidelines for a couple of months, we took to her social media account for this fantastic “now" photo. Although she’s been gone for way too long as of late, she’s still doing her thing away from the camera as the Brand Ambassador. It also helps when you look that good, Barclays’ should of made Steph her own statue for her presence at the event, never mind a jersey...

The big take home the WWE Universe took away from the fantastic pic is the fact that Steph still look incredible despite her lack of TV time getting written off the show after crashing through a table at this past WrestleMania. We anticipate her return which should take place in the very near future.

11 Then – ECW Never Looked Better


When we think of “assets”, the mind immediately races to T & A. However, for Stephanie, not only does she have both those going on, but her facial features are among the very best in the entire WWE Universe. Looking at this throwback shot, you seriously get lost in Steph’s eyes and forget that she’s wearing a silly ECW hat. Man was that storyline ever terrible.

Working as a heel alongside brother Shane, Steph added her villainous persona to the storyline becoming an anti-WWE figure. That part of her career would be her final heel work of the early 2000s. After the Invasion storyline she rivaled her husband Triple H taking the corner of Chris Jericho at WM X-8. Steph would leave after ‘Mania only to return months later in the summer, this time, serving as a babyface GM.

10 Now – Humanitarian Awards


Stephanie McMahon has done a lot of good for the company throughout her role as the Brand Ambassador. Steph has taken the WWE’s brand to new heights, especially with charitable organizations as the WWE is constantly working with great causes. Now, more than ever before, the WWE’s global standing is better than ever, yes, the new Wellness Policy has a lot to do with it but Stephanie’s work shouldn’t be undercut as she’s done a hell of a job when it comes to PR work.

In this photo, Stephanie appeared at the Sports Humanitarian Awards representing the company in LA. Rocking a fantastic dress, the WWE never looked better as Steph flaunts her “assets” on the red carpet. How she’s in her 40s, we’ll never understand.

9 Then – Christmas Chest Nuts


We likely found Stephanie’s exact reaction to Raw being live the Monday of Christmas day... Of course, Steph is a mother of three beautiful daughters so she can’t be exactly thrilled at her dad’s decision to put the show live. Oh, and Raw will also be live New Years day, Vince is just ruthless this year!

Back in the late 90s and early 2000s, the WWE didn’t take such steps as the X-Mass show was usually taped or changed with a special type of episode. Nonetheless, the WWE loves the holiday theme from back to the origins of the company. Looking at picture above of McMahon with the fantastic red “cleavage friendly” shirt, we too have no problem with the WWE and the holiday. If Vince expects us to watch the show, we better get a similar attire this upcoming X-Mass and not a tag match featuring the Big Show (no disrespect to Big Show, but we’d rather see Stephanie in “Not So PG” attire).

8 Now – She Works Out


A big change in the modern day Stephanie McMahon is her new found love for fitness. For that reason, you can argue that she’s in better physical shape today than she was back in the day. With Triple H building his own gym in the basement of his beautiful home, Steph has also taken a liking for staying in shape.

The picture you see above is Stephanie along with a plethora of other WWE Divas taking part in a special WWE Fitness DVD. Now there won’t be a sequel to the product given how terrible the sales were but looking a Steph’s attire, it’s certainly worth a look, or two... Rocking the yoga pants and performing multiple positions, we hate Paul Levesque that much more.

7 Then – The Blonde Days


Yup, that’s right, for those of you that forgot, the “then” Stephanie endured a run while rocking a beautiful head of blonde luscious hair, Tiger Woods, a lover of the blonde type is likely drooling somewhere. Future match, Triple H against Tiger Woods, “Golf Club On a Pole Match” (the booker: Vince Russo).

Okay, we got a little carried away there but seriously, this throwback picture proves that Stephanie is hot as both brunette or blonde. She showcased the look during her 2005 return and it was welcomed by the WWE Universe, especially due to the fact that she paired it with a revealing black top of the “Not So PG” nature. Wise move Steph, wise move. We wonder if the “now” Steph will ever revert back to such a look. What do you guys think, blonde or brunette?

6 Now – What An Entrance

Forget about throwing water all yourself and spitting it out, this is truly the way to make a real entrance as Stephanie looks simply GLORIOUS! In her perfectly fitted blue dress, most of us even forgot Triple H existed in the photo. The power duo was entering the Citrus Bowl for WM 33. The bus they got off of was no ordinary bus, the couple tours with it around the US, even bringing their kids in the state of the art vehicle. Stephanie admitted the two even got changed on the bus for the big day, seems like Steph in particular did one hell of a job as she has us seeing blue.

The post was published on Instagram back in early April, and her on-screen involvement has been limited since then.

5 Then – What Neck Brace?


The “then” Stephanie scores some major points in this battle as many fail to realize she’s wearing a neck brace, after all, rocking such a tightly fitted body suit dress, most people are looking elsewhere. This picture took place back in the prime of Stephanie’s heel run during the early 2000s. McMahon had countless memorable feuds against the likes of The Rock and Chris Jericho, who can forget those fantastic monologues when Steph would get ripped to shreds, nowadays, you won’t see anything of the sort given her high powered status with the company. Today, she’s usually the one doing the ripping.

We hope this attire is somewhere safe, and hopefully, up on a wall. In terms of hottest Stephanie McMahon outfits of all-time, this was is certainly right up there among the top.

4 Now – Another Standout Appearance


One of Stephanie’s biggest public appearance in recent memory took place at the exclusive Cannes Lions Festival which was littered with high profile faces from around the world. The festival is meant for those in advertising and creative communications, hence Stephanie’s involvement. Not only was Steph representing the company a huge deal, but she also couldn’t of done the WWE any better given her fantastic look throughout the festival. There’s a reason she’s in such a position and it’s not just because of her tremendous outgoing attitude. Dressed to absolute perfection with the dress, she made us proud!

The dress just showcases a different side of Stephanie nowadays and although it’s a little more PG, some make the claim that it’s even better than the “then” look, appearing classier than ever. Do you agree?

3 Then – Zebra Stripes


Some remember the 2002 No Way Out event for the debut of the nWo. However, we here on The Sportster acknowledge the event for Stephanie and her portrayal of a WWE referee. Seriously though, Steph and the zebra colors were a perfect fit, it’s no wonder her husband lost the match that night but in truth, he was the real winner after the show.

Stephanie’s involvement in the match was meant to provide heel heat against Triple H. It was the only time the two were heated rivals. On the particular night, Steph would help Kurt Angle defeat Triple H for the number one contendership for the main event of WM X-8. Of course, the decision would be overturned in the following weeks but you can’t help but to think how much better Jericho versus Angle could have been in the main event of the show... Sorry Hunter.

2 Now – Still The “Girl With The Shy Smile”


For the top “now” selection, we didn’t take a pic in where Steph’s flaunting her goods, instead, we went for the sentimental picture showing Stephanie still rocking the shy smile to this day. Mick Foley said it best during a Raw promo, back when she was debuting, Stephanie was known backstage as the “girl with the shy smile”. Truth be told, not only was Mick correct but in fact, as evidenced by this picture, Steph is still that person.

Behind the scenes she’s said to be the most heart warming McMahon family member. And in such pictures like the one above during her ITV cameo in London, she still portrays the great smile which is without a doubt, one her top “assets” both then and now. Like a fine wine, she just gets better with age.

1 Then – SmackDown Days


Some might say this picture is the knockout blow in the article, however, that’s still up for debate as the current Stephanie is mighty hot as you’ve seen throughout this article. Though, as we stated in the very first entry, Steph’s steamiest time period according to the people was during her GM run atop of SmackDown during the early 2000s. In a persona we’ll never see again (actually never say never when it comes to the WWE), Steph was a flirtatious figure while controlling the SD brand. She was involved in various “Not So PG” skits, including the one you see in the picture above which is arguably her most memorable backstage segment given a certain “asset” (or “assets”) coming out to play.

So there you have it folks, the question remains, the Steph of then or now, let your voice be heard via Facebook!

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