The bosses daughter! The Billion Dollar Princess! Need we say more?

Fraternizing with the 'wrestlers' was forbidden in the McMahon family but almost as soon as the 25 year old (in 2001) Stephanie arrived on the scene in June 1999, she began dating Test. This, of course started a full blown family feud between Stephanie & her brother Shane. Even Shane's long time friends the Mean Street Posse got into the act which didn't give Test much of a break battling his sweethearts brother or a gang of thugs, and sometimes both.

Just when Stephanie and Test were to be married she was injured during the Rebellion PPV in the UK and she lost her memory. Finally in November 1999 the wedding day arrived and just as the minister asked if anyone could show why the two should not be married Triple H stepped onstage. He informed everyone that he had a video they should view first.

The video showed Hunter driving through Las Vegas in a car and pulling into a wedding chapel on the Vegas Strip. As he drove up to a window to get married, we saw his bride to be - a sedated Stephanie McMahon! Triple H said the vows for both himself and Stephanie, put a ring on her finger, and said "I do." They were married! Stephanie had been knocked out by the drink she was offered earlier at her bachelorette party!

The blissful union ended up producing the McMahon-Helmsley Era of the WWF. This pretty much constituted Stephanie and Triple H throwing their weight and big ego's around and generally making most other wrestler's lives miserable. Some of the highlights of her conniving ways during 2000 included calling her mom a bitch and then slapping her in the middle of the ring and illegitimately gaining the WWF Women's Championship (with the aid of Triple H and X-Pac) from Jacqueline while holding onto it for 2-1/2 months without ever defending it. When she finally did defend it against Lita she feigned a knee injury to distract the ref while Kurt delivered an Olympic Slam to Lita. She finally lost the belt to Lita in August 2000 and spent the end of the year plotting with Daddy and getting Linda McMahon committed to a mental hospital and Daddy in full control of the company.

To start off the year 2001 Stephanie violently objected to her Daddy making Trish Stratus his new playtoy. This turned into a full blown feud between the two women during the Royal Rumble where Stephanie attacked Trish. A match was set up for the two at the No Way Out PPV in February, which Stephanie won with the aid of Stephen Regal. As a final insult Vince turned on Trish the next night on Raw and he allowed Stephanie to completely humiliate his former girlfriend by having Stephanie push Trish's head into a horrible bucket of goop and then using the mop on her!

In May 2001 the McMahon-Helmsley Era came to an abrupt halt during a Raw broadcast. The Tag Team Champions Stone Cold Steve Austin and Triple H took on Chris Benoit and Chris Jericho where Triple H severely injured his knee at the end of the match and Jericho covered Austin for the win. For the next few weeks Stephanie's role was unclear and it was rumored that she was going to spend more time writing storylines, but once again the "Billion Dollar Princess" popped up with a new angle that would insure the wrath of Daddy. In July 2001 Stephanie decided she could not be outdone by her brother who had bought the WCW earlier in the year, so it was announced that Stephanie was now the owner of the ECW.

Now brother and sister combined the ECW and WCW into the Alliance, and over the next few months antagonized Dad while Chris Jericho began a hilarious campaign of degrading Stephanie verbally any chance he could get. This included pointing out what everyone had already noticed - Stephanie's breast augmentation. This caused Stephanie to enlist the aid of Rhyno and then Rob Van Dam to shut Y2J's mouth, but neither were really successful, much to the dissatisfaction of the Princess. Also about this time rumors began to crop up about a developing storyline that would have Steph and Triple H getting a divorce, but it never materialized.

In November 2001 rumors appeared that Stephanie and Triple H were now a couple in real life (almost an exact year after Chyna announced she was single). A few weeks later it came out on the Howard Stern show during an interview with Chyna that Stephanie and Triple H were a couple and that Stephanie was the reason they had broken up.

To start off 2002 Stephanie tried to throw her weight around and threaten everyone with the fact that "The Game" was coming back. After a 7 month layoff Triple H returned on the first Raw in January, to the delight of the Madison Square Garden crowd. The following Thursday on Smackdown she dropped a complete bombshell. She stated that without her business savvy and brains Triple H never would have been the success he was in the WWF. She also stated that he never would have been Federation Champion nor would he have returned after his injury without her. She said Triple H appreciates her, and with her by his side, he will go on to win the Royal Rumble and become Federation Champion! Stephanie went on to say that Triple H knew that her brains would get him further than any other superstar. She reminded the fans that The Game was back, and she was The Game's wife. You can probably expect the divorce angle to pop up sometime soon since she's already irritating Triple H.

Triple H made a comeback as a face, but the couple began having problems. The couple "divorced" after Stephanie claimed to be pregnant in order to trick Triple H into renewing their marital vows. The split was acrimonious to say the least; Triple H literally complied with the "fifty-fifty" divorce settlement by giving Stephanie the front half of her Corvette and Stephanie claimed that Triple H had abused his bulldog Lucy, in order to gain custody to spite him. Lucy was later run-over by a limousine, much to the distress of Triple H, who chased Stephanie around the ring and humiliated her by pulling her into the ring by the seat of her pants, in the process revealing part of her buttocks.

On July 18, 2002, Stephanie returned to the WWF (renamed WWE following a lawsuit from the World Wildlife Fund) as the general manager of SmackDown!. She feuded with RAW General Manager Eric Bischoff throughout 2002, though the enemies inexplicably shared a kiss at a Halloween party in which Stephanie was dressed as a witch and Bischoff was disguised as her father underneath a mask. Stephanie was given credit for the return of the WWE United States Championship and for the creation of the WWE Tag Team Championship. She was also credited with signing Hulk Hogan back to SmackDown!, which caused friction between herself and her father in the storyline that followed.

Stephanie was involved in an amusing segment with Triple H at the RAW 10th Anniversary show, where the two were winners of the "Shut Up and Kiss Me" award. Stephanie jokingly stated that "where else can you get drugged up at your own wedding, marry a loser, fake a pregnancy, get divorced and then make a comeback to head up the greatest wrestling show on TV today, SmackDown?"

Stephanie was ousted from her position after a long feud with her father, Vince McMahon. Though he originally had been the one to appoint Stephanie as the General Manager, he began to resent her growing independence as well as her attempts to stop him from pursuing an affair with Sable. Stephanie wanted him to fire her but Vince wanted her to "respectfully resign". When Stephanie refused, Vince put her in a series of matches with such superstars as A-Train and Brock Lesnar which led up to the first ever "father daughter I quit match" at No Mercy 2003. Stephanie McMahon was accompanied by her mother, the CEO of WWE Linda McMahon and Sable accompanied Vince McMahon in their match. Throughout the match Linda and Stephanie exchanged slaps with Sable when she tried to interfere. Stephanie did not say "I Quit", but lost when Linda, at ringside threw in a towel on her behalf because Vince wouldn't release a choke he had on her with a lead pipe. After the match, Vince put his hand over Linda's face and shoved her to the canvas when she tried to see about her daughter. Paul Heyman succeeded Stephanie McMahon as the new Smackdown! General Manager.

On March 13, 2004, Stephanie attended the WWE Hall of Fame induction ceremony, and on September 23, she appeared on the fifth year anniversary episode of SmackDown! and talked about her favorite SmackDown! moments.

Stephanie returned to WWE TV on October 3, 2005 at WWE Homecoming, when she confronted Stone Cold Steve Austin after he had stunned her father and brother. She slapped Austin, but was then herself stunned. She appeared on RAW for two weeks thereafter, and was involved in the firing of Austin's friend, RAW announcer Jim Ross and the booking of a match between Ross's replacement, Coach, and Austin at Taboo Tuesday 2005, with Ross's WWE future on the line. However, the match was cancelled after Austin suffered a minor injury that, combined with his unwillingness to job to Coach, led to him no-showing the subsequent episode of RAW.

Stephanie had nasal surgery to help her breathing several days before the Eddie Guerrero RAW tribute show that prevented her from appearing in person. She returned to RAW on December 5 as a witness in the mock trial of Eric Bischoff, and claimed that Bischoff had "violated" her by kissing her three years earlier. She called the judge, Vince McMahon, "daddy".

A visibly pregnant Stephanie McMahon returned on the March 6, 2006 episode of RAW, approaching Shawn Michaels backstage and claiming to have abdominal pains. When Michaels left to get her some water, Stephanie pulled out an unmarked substance out of her brassiere and poured it into his bottle of water, causing him to become groggy during his match against Shane McMahon later in the night, which he lost as a result. Stephanie also appeared at the WWE Hall of Fame induction ceremony on April 1, 2006 and in a backstage vignette with her immediate family at WrestleMania 22.

Stephanie McMahon returned at Wrestlemania 23 backstage, visiting her father before his Battle of the Billionares match. She brought her "daughter" with her (it was not her daughter but just a baby stroller with a camera inside to get a closeup on Mr. McMahon), to wish him good luck. She also shown her hair dyed from blonde to a dark brown.