15 Hottest Examples of Stephanie McMahon's WWE Evolution

Stephanie McMahon aka, the boss’s daughter, aka the "billion dollar princess," has graced WWE television ever since 1999. During that time she became a major player in many of WWE’s biggest storylines

Stephanie McMahon aka, the boss’s daughter, aka the "billion dollar princess," has graced WWE television ever since 1999. During that time she became a major player in many of WWE’s biggest storylines and moments. She has evolved into one of the most important figures on and off WWE television.

Stephanie currently serves as Monday Night Raw's commissioner. Fans of the dominant wrestling promotion definitely remember when she was an onscreen heel with the McMahon-Hemsley Era during the year 2000 or when she was the innocent face that had to be protected from a demonic Undertaker. Then again, how about when Stephanie was the SmackDown General Manager in 2003? Hell, even when she was the co-leader of the Authority it felt like she was involved in every opening promo.

It can be argued that we have yet to see the best from Stephanie...It can also be argued that not only have we seen the best of the “Boss’s Daughter,” we are still being graced by her presence week in and week out on Monday Night Raw. Well, it’s time for the WWE universe and fans of good lookin’ women to take a trip down memory lane and witness the 15 hottest examples of Stephanie McMahon's WWE Evolution.

15 She Was A Hot WWE Women's Champion


Nothing needs to be said in this picture, only seen. The already powerful Stephanie McMahon became more powerful when she won the WWE Women’s Championship on SmackDown on March 30th, 2000. She was deep into the McMahon-Hemsley Era storyline and her father’s on-screen persona, Mr. McMahon, was a face. He “punished’ Stephanie by putting her in a championship match with the reigning women’s champ Jacqueline.

Stephanie, who had little if any ring experience, spent most of the match running around and getting her behind whipped. Tori, a DX member at the time (in what was perhaps the crappiest version of the stable), interfered when the ref wasn’t looking and DDT’d the champ. HHH yelled at Stephanie to pin the fallen star and after the 3 count Stephanie earned her first and only Women’s title.

As you can see, she looks pretty hot with that evil, frisky smirk, with the championship belt on her shoulder, along with that vintage Stephanie McMahon Hemsley t-shirt.

14 Stephanie’s Above The Throne


Here’s a more recent picture of the boss’s daughter as she wears a black tank, black pants, and black heels with her hair blowing in the air. We also know she loves to flaunt her voluptuous frame. This picture is HOT because not only do we see Steph’s beauty on display, we get a nice dose of her bad, rich daughter persona and the image of her with the chair knocked over shows that the Queen’s power perhaps knows no limits.

As Raw’s Commissioner, she has the final say, and if you mess with the queen you’re gonna pay (okay that was corny, but it isn’t that far-fetched that she would say something like this right?...Yeah). One could also argue that Stephanie has gotten hotter with age, something that most women and men would kill for. I guess that’s another reason to be jealous of the “billionaire princess.” Be honest to yourself, you know you want some.

13 With Authority


There have been many nicknames for Stephanie over the years, probably enough to construct an entire list. I wonder what Chris Jericho circa 2001 would say about this particular shot. Stephanie knows she’s hot and knows she’s powerful; so flaunting her business attire and looking back in flirtatious fashion is only a reminder that there’s nothing anyone can do to even think about having her. Is there any harm in being attracted to a hot woman that’s perhaps, a little evil (in terms of her on screen persona)?

The most alluring aspect of this shot is Steph’s piercing blue eyes; they’re cold enough to create a hole straight through one’s heart. This shot also shows that Stephanie doesn’t have to show skin or her well known assets to melt the screen. She has one of the most beautiful faces out of all the ladies of the WWE and for this pose having her bad girl side breathe through is the correct antidote for men who need a real woman in their life.

12 Flourishing As SmackDown's General Manager in 2003


Anyone who witnessed the boss's daughter from when she made her on-screen character debut in 1999 to present day may notice a couple of additions to Stephanie’s frame. Let’s just say back in 2001 everyone (especially Chris Jericho and The Rock) noticed Stephanie had significantly grown in the ta-ta department. Y2J and The Great One may have made some rather hilarious remarks about Steph’s heel character over the years, fans of Steph have most likely not complained.

This pic is from 2003, when Steph was in her mid-20s and obviously not timid when it came to showing off her lady lumps. SmackDown during 2002-2003 is fondly remembered as some of the WWE’s best programming periods ever, and few will forget Steph’s time as the general manager on the show. She gave us many eye grabbing visuals just by doing nothing but standing there. Here Stephanie sports the bangs, that black collar, and provides every SmackDown watcher with a nice bit of cleavage.

11 The Bootylicious Billion Dollar Princess


There’s so much talk about Stephanie’s boobs that we rarely talk about her very nice and defined booty. While it may not quite be enough of a booty to make the Top 16 WWE Booty Revolutionaries list, it’s certainly worth a mention (no shame in that Stephanie…). She works out so damn much, how could that part of her curvaceous frame not be nice?

This recent shot is from Steph’s time in The Authority (AKA The Corporation 2.5 or The McMahon Hemsley Era Part 2). She sports a tight curve accentuating outfit that clearly highlights her booty as she gives HHH a hug. As we can see, HHH is having a tough time not grabbing it while it’s happening (ugh, freakin’ PG Era, SMH). It might be time to admit to ourselves that we are definitely jealous The Game right here. This isn’t the last time we will see Stephanie’s other notable asset on this list, so be patient.

10 Blazin' At WrestleMania 32


Stephanie’s WrestleMania 32 attire shows once again that she knows she looks great in black and it also shows that she very well might be in better shape in her late 30s than she was in her early 20s. Stephanie showed off this fierce attire during then WWE World Heavyweight Champion HHH’s entrance. During this time the Authority angle may have worn thin with the WWE universe, but not on this night. Why? Because HHH was facing Roman Reigns, the WWE’s most hated face at the moment.

Smarks didn’t want to see this match happen as it came off as forced due to the obvious company movement to make Roman Reigns “THE guy.” Stephanie went a little old school and took a spear from Roman Reigns on route to her husband eating the pin and losing the championship. If anyone chooses to re-watch this rather lackluster main event again, just watch Stephanie; she’s far more entertaining than the actual match.

9 Always Reppin' The Company...


This cute picture is of Stephanie from the Attitude Era sporting a WWF New York t-shirt (remember that place?) Yes, the WWE was so white hot in the Attitude Era that they saw fit to open their own restaurant in Times Square. This place would be the location of many events and broadcasts featuring wrestlers that didn’t happen to be on Raw or SmackDown. The restaurant slash nightclub closed in 2003.

Now that the history of a now defunct Attitude Era laden restaurant has been spoken of, it’s time to place our attention back to Steph, who looks uber adorable less like a power hungry maniac in this photo. Sometimes being cute is the hottest thing a woman can do. Steph’s almost sassy “check this out” demeanor perhaps echoes a bridge between the innocent Stephanie who was a damsel in distress and the, conniving, evil, shrieking bad girl who will do anything to get her way. This is by far one of the more approachable pics of the boss’s daughter around.

8 The Queen’s Sledgehammer


As we all know, Stephanie is married to the COO Triple H. Stephanie and Triple H are THE power couple of the WWE. They flaunt their hotness and work ethic whenever and wherever possible. So why wouldn’t the daughter of Vincent Kennedy McMahon take a photo where she sits on a throne with that devious smirk with hands resting on the imposing main weapon of her husband?

Triple H, aka The Cerebral Assassin’s, signature weapon is the dreaded sledgehammer. He wields it whenever he needs to inflict severe punishment or when he needs a great equalizer to save his ass. It’s won him championship matches and gotten him disqualified. Remember the old saying, “behind every powerful man is a powerful woman?” Well, we see that on full display right here as Stephanie makes sure that everyone knows that she’s the wife of the COO and she will wield her man’s sledgehammer whenever and wherever she pleases. Take that for what it’s worth.

7 Special Guest Referee At No Way Out 2002


This is a picture of Stephanie McMahon being the special guest referee at No Way Out 2002. The match was a number one contender’s bout between Triple H and one of his biggest rivals Kurt Angle. The storyline between these three went all the way back to the summer of 2000 when there was a heavy love triangle tease. Stephanie made sure that all eyes were on her referee shirt, which was clearly customized for her frame. Who in their right mind wouldn’t want a hot referee like Stephanie making sure there’s a pinfall or a submission?

Stephanie hit her eventual real-life husband with a chair, ensuring victory for Kurt Angle. Stephanie and HHH’s on-screen characters would briefly split in the year 2002, especially since HHH was coming back from his quad injury as a full blown babyface. Stephanie continued her reign as a heel and would eventually go on to serve as Smackdown’s General Manager later in the year.

6 More Stephanie From The Attitude Era

Via, WWWL -

This steamy shot of Stephanie McMahon is yet another one from the Attitude Era (or if you want to get more technical, the invasion era that can still be considered in the Attitude Era). As with other photos we’ve seen on this list, the boss’s daughter clearly loves to dress in color black. Stephanie is feisty, devious, and flat out hot in this one. This photo sums up her heel persona. She’s wearing fishnet stockings while wearing leather shorts and a black tanktop. Steph’s demeanor and her facial expressions sum it all up yet again as she flashes that she-devil of a smile. It was during this era that Stephanie became a Women’s champ and continued to be a major force in the main event storylines. Stephanie interacted with the likes of: her father, Vince McMahon, HHH, The Rock, Chris Jericho, Kurt Angle, The Undertaker, Mick Foley, and more. Steph’s contributions to the hottest period in WWE history are still felt to this day in the form of recent stables and storylines that echo the past.

5 Vintage She Devil 101


This obscure shot of Stephanie is from around the year 2000, when the McMahon Hemsley Era ruled the WWE airwaves for most of the year. It was a landmark year for Stephanie because her faction led the company in storylines. She won the women’s title, was in the background of a McMahon feud with The Rock, Mick Foley, and she and HHH had their faces planted on the side titantrons during every Monday Night Raw. Stephanie and HHH pretty much opened every Monday Night Raw. Their feud with The Rock and becoming the main antagonists for faces to take down helped the WWE continue its ratings onslaught, despite the absence of the face of the Attitude Era “Stone Cold” Steve Austin. Stephanie McMahon had become fully engrossed in her heel turn and showed it physically with her hair, expressions, and style of dress. We slowly started to see a more provocative less covered Stephanie and we weren’t complaining.

4 Don't Cross The Boss!


This is definitely a side of Stephanie that WWE viewers have seen on multiple occasions. She may look very good in a plethora of photos, but when it comes down to it Stephanie McMahon is what she is; a McMahon.  She carries the legacy of the name and the WWE is apart of her blood.  Stephanie flaunts her looks in this provocative business suit.  Her hair is out and she has that "don't cross the boss" McMahon look, except it looks way better coming from Stephanie than her father.

While this picture is of a younger Stephanie, it certainly gives a glimpse of the now when it comes to Stephanie handling business in and out of the WWE.  Don't let the looks fool you, Stephanie's on screen persona will have no problems letting everyone know that she's a McMahon and she's had more success and power than many of us will ever have.  We can still look though!

3 Stephanie's Toned Up In 2016


Stephanie McMahon has been at the forefront of the WWE for almost 20 years now. We have seen the boss’s daughter grow up right before our very eyes on WWE TV. It can certainly be argued that Stephanie has gotten even hotter with age. The Billionaire Princess and the Queen on the WWE’s power couple throne sports a body that many women half of her age would do almost anything to obtain. Stephanie sports a black tank top, green athletic shorts, and a pose that’s sure to make people jealous. Stephanie has gotten so involved with her fitness that she’s even starred in her own fitness video with other WWE Divas titled Fit Series. It also doesn’t hurt that she’s married to a fitness freak. Anyway, Stephanie’s made sure to take care of herself over the years and regardless of if you love or hate the woman’s on screen or off screen character you’ve got to respect her work ethic.

2 Stephanie's Got It, So She'll Flaunt It (Especially In 2003)

Via Forums

The show? SmackDown. The year? 2003. Fade in. There’s nothing except the crowd noise in the background. We fade in to see revealing heels and a great set of legs. The camera slowly moves up as we now see a nice short skirt containing a nice round bottom. Anyone who watched was thinking “Damn! Who’s this!?” The curvy woman stands up, turns around and yes, there she is, Stephanie McMahon in her absolute prime as SmackDown's General Manager addressing the WWE universe before it was called the WWE Universe.

This was the moment that Stephanie put WWE fans on notice; Stephanie was the leader and had no qualms about flaunting every inch and curve of her body. She wanted everyone to know that she was embracing her hotness yet still contained that sense of power that she and her family have within the WWE. Stephanie’s lovely curves became the butt (pun intended) of some funny SmackDown moments and segments, including John Cena basically begging to smack Steph’s ass later in her tenure.

1 When Stephanie Was Innocent in 1999.


Stephanie McMahon made her WWE Television debut in 1999 during the Higher Power storyline. The Undertaker was at his darkest and most demonic, sacrificing people left and right. The “Deadman” abducted Stephanie and proceeded to try to sacrifice hereby placing her on his iconic symbol, before she was saved by “Stone Cold” Steve Austin. This version of Stephanie McMahon’s on screen character is a sweet, innocent “daddy’s little girl.” The complete and utter 180 from the “billionaire princess” and “devilish wife of HHH” persona that would dominate most of her WWE career is amazing. Sometimes less is more is the hottest of the hot and that innocent image of Stephanie McMahon harkens back to a simpler time and a Stephanie that was still molding her eventual path in her early 20s. If there was a poll that was conducted of which version of Stephanie was perhaps the hottest, there’s a strong chance the woman from the photo above would rank pretty damn high!

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15 Hottest Examples of Stephanie McMahon's WWE Evolution