McMahon began his on-screen career as a referee named Shane Stevens in 1990 and was the first performer to walk out to greet the audience at WrestleMania VI. Shane McMahon also refereed during the 1991 Royal Rumble match. He soon left behind the blue shirt and bow-tie and took on the role of a backstage official at WrestleMania VIII in an attempt to break up a brawl between Randy Savage and Ric Flair after he and other officials failed to keep Miss Elizabeth away from ringside.
McMahon became a regular while being an on-air character in 1998, during his father's on-air feud with Steve Austin. In the early days of that angle, McMahon offered support for his father in cameo roles, but he did not become an enforcer like Gerald Brisco and Pat Patterson. McMahon was a color commentator on Sunday Night Heat alongisde Jim Cornette and later Kevin Kelly, and announced with Jerry Lawler on the 1999 videogame WWF Attitude. Concurrently with this, McMahon took a role as a regular character, turning on his father by signing Austin to a contract after Vince demoted him to the position of referee. Yet at Survivor Series, McMahon turned heel by turning on Austin and became an official member of The Corporation.
In February 1999, McMahon moved away from the commentary role on Heat and became a key component in the Corporation angle, winning the European Championship from X-Pac. The two met in a rematch at WrestleMania XV; McMahon got help from his childhood friends the Mean Street Posse and Triple H, who turned on X-Pac during the match, to retain the championship. McMahon then retired the title, wanting to retire as an "undefeated champion". McMahon later gave the title to Mideon, who found it in McMahon's duffel bag, thus reactivating it.
After WrestleMania, Vince briefly made his second face run and McMahon took control of the Corporation. With wrestlers such as Triple H in this new faction, McMahon feuded with his father and a new faction made up of former Corporation members, The Union. On the UPN pilot for SmackDown!, McMahon joined forces with The Undertaker and the Ministry of Darkness to form the Corporate Ministry. Eventually, Vince was revealed to be the mastermind behind this faction, and his face turn was explained to be a plot to get the WWF Title off Austin. Austin then met Shane and Vince in a ladder match at the King of the Ring for ownership of the WWF, as in the storyline, Austin had 50%, which was assigned to him by Linda and Stephanie McMahon, upset by Vince and McMahon's complicity in the storyline kidnapping of Stephanie by the Corporate Ministry, while McMahon and Shane each had 25%. Shane and Vince won the match when a mystery associate raised the briefcase out of Austin's reach when he climbed the ladder, allowing Vince and Shane to grab the case and regain 100% ownership of the WWF.
With his ownership reinstated, McMahon shifted his sights to, then babyface, Test, who was kayfabe dating Shane's sister, Stephanie. Shane disapproved of the relationship, feeling Stephanie was dating "beneath the family's standards", and wound up feuding with Test. With help from the Mean Street Posse, McMahon made Test's life a living hell. At SummerSlam, McMahon met Test in a "Love Her or Leave Her" match, with the stipulation being that if McMahon won the match, Test and Stephanie could no longer see each other, and if he lost, McMahon would give his blessings to the pair. Test was able to get the win, and McMahon eventually settled his differences with Test, thus making his second face run by becoming his ally. Later in the year, Stephanie turned heel, siding with her new kayfabe husband then-heel, Triple H (the two began their off-screen relationship around this time, but did not marry in real life until 2003). With that, the McMahon-Helmsley Faction began, and all of the other McMahons disappeared from television.
At No Way Out, McMahon made his return as a heel again by helping The Big Show defeat The Rock. This started the road to WrestleMania 2000, where in the four-way main event each wrestler had a McMahon in his corner. The Rock had Vince, the Big Show had Shane, Triple H had Stephanie, and Mick Foley had Shane's mother, Linda McMahon. The Big Show was the first man eliminated, and soon after he and McMahon went their separate ways. This led to a match between the two at Judgment Day, which McMahon won after receiving help from Test and Albert, amongst others. Over the course of the next several months, McMahon allied himself with other heel wrestlers, including Edge and Christian, who helped him win the Hardcore Championship from Steve Blackman. McMahon met Blackman in a rematch at SummerSlam, losing the title after falling 40 feet through the stage (McMahon climbed up the set running away from Blackman, who gave chase and hit Shane with a Singapore cane, knocking him off). McMahon then disappeared from television, making occasional cameo appearances.
In 2001, McMahon made his third face run by once again feuding with his father, Vince. The feud with Vince was due to the elder McMahon's (kayfabe) affair with Trish Stratus and Vince's spite and demand to divorce Linda McMahon. At Backlash, McMahon was in a Last Man Standing match against the Big Show. In one of the most memorable moments in professional wrestling history, McMahon performed the Leap of Faith (from the top of the scaffolding), causing McMahon to get the victory when Show could not answer the 10 count.
McMahon then began a feud with Kurt Angle. By the King of the Ring, on June 24, McMahon's feud with Angle had culminated. After already participating in two tournament matches that night, Angle wrestled McMahon in a Street Fight. After a suplex on the hard floor, Angle was thought to have cracked his tailbone. Angle also delivered an overhead belly to belly suplex through the plated glass stage set, but McMahon did not break through on the first attempt, causing him to fall head-first onto the concrete floor. After a successful second attempt, Angle was to put him through a second plate back out to the stage and again failed two more times. The match also had Shane missing a shooting star press and ended with Angle performing the Angle Slam off the top rope before scoring the victory over a bloodied McMahon.
Shane and his sister, Stephanie, then took control of the Alliance during the Invasion. Ultimately, The Invasion came to a head at Survivor Series in a match to determine which power would ultimately have control. The team, each respectively representing The Alliance and the WWF, of McMahon, Steve Austin, Kurt Angle, Rob Van Dam, and Booker T lost to the team of The Rock, Chris Jericho, The Undertaker, Kane, and the Big Show. The following night on Raw, Vince publicly fired both Shane and Stephanie, which Shane took in stride, admitting that he lost to the better man, while Stephanie pleaded with her father before being forcefully removed from the arena. Following the destruction of the Alliance, McMahon remained off-screen, eventually briefly reappearing three times during 2002 to 2003.
Shane McMahon made his first on-screen appearance in two years on an episode of Smackdown before WrestleMania XIX, watching his father's training in the gym to prepare his match against Hulk Hogan. At WrestleMania XIX, he went to check on his father's welfare following a street fight with Hulk Hogan, with Hogan welcoming Shane in the ring and then walking out. He turned face once more in the summer of 2003 by getting involved in a feud with Eric Bischoff (who had made improper remarks and gestures to Shane's mother Linda). He defeated Bischoff in a street fight at SummerSlam. McMahon also got involved in a rivalry with Kane after Kane gave Linda a Tombstone Piledriver because she did not name him the number one contender to the World Heavyweight Championship. Their feud culminated in McMahon losing a Last Man Standing match at Unforgiven and to a first ever Ambulance match which he lost after a brutal match at Survivor Series.
After Survivor Series, McMahon left Raw to focus his attention on the executive creative staff and on his new family. At WrestleMania XX, McMahon appeared briefly on camera during the opening of the event with Vince and his newborn son, Declan. In a special 3-hour edition of Raw in October 2005, billed as WWE Homecoming, all four members of the McMahon family were given a Stone Cold Stunner by Stone Cold Steve Austin. The following week, Vince demanded an apology from ringside commentators for not coming to his family's aid, which developed into a new feud. McMahon also appeared at Survivor Series, though he did not appear on television. He can be seen on the DVD extra backstage talking to Theodore Long, when The Boogeyman tried to scare off McMahon, who made no deal about it.
McMahon turned heel once more by again siding with his father to help in the feud with Shawn Michaels. At the 2006 Royal Rumble, McMahon eliminated Michaels by throwing him over the top rope. After weeks of attacks from behind by McMahon, one of which saw McMahon force an unconscious Michaels to kiss Vince's rear end, McMahon and Michaels faced each other in a Street Fight on the March 18, 2006 edition of Saturday Night's Main Event. In a fashion similar to the real life Montreal Screwjob, McMahon put Michaels in the Sharpshooter as Vince called for the bell and gave McMahon the victory. The McMahons' feud with Michaels took a religious turn after WrestleMania 22 (where Michaels defeated Vince McMahon). Vince claimed that Michaels's victory was a result of "divine intervention" and booked himself and his son in a match at Backlash against Michaels and his tag team partner "God".
This feud later enveloped Triple H, who the McMahons had enlisted to take out Michaels. Triple H was getting frustrated with this, as it was distracting from his quest to regain the WWE Championship. Triple H wound up bashing McMahon with his signature weapon, the sledgehammer, in what was considered to be an accident that put McMahon out of the ring for a while. Vince (and later McMahon, who had recovered) sought to humble Triple H and get some retribution. Triple H then began a feud with the McMahons shortly after, leading to his siding with Shawn Michaels and the reformation of D-Generation X (DX). At SummerSlam, McMahon, along with his father Vince, were defeated by DX. About a month later at Unforgiven, The McMahons and then ECW World Champion The Big Show faced DX in a Hell in a Cell match. McMahon was injured after Michaels elbow dropped a chair which was around McMahon's neck. DX emerged victorious at Unforgiven, and McMahon disappeared from television.
On the March 5 edition of Raw, McMahon came back to inform his father, Vince, about the "guest referee" for the "Battle of the Billionaires". He told him that their opponents on the Board of Directors had won the vote, 5-4. The McMahons had intended for McMahon to be the referee. Instead, the guest referee turned out to be the McMahons' old rival, Steve Austin. During the "Battle of the Billionaires" match at WrestleMania 23, McMahon's attempt to interfere on his father's behalf was stopped by Austin. During the match, McMahon was able to hit the Coast-to-Coast dive with a trash can into Bobby Lashley's face. On April 9, McMahon officially joined the Vince/Umaga/Lashley feud when he faced Lashley for the ECW Championship in a Title vs Hair match which ended in McMahon getting disqualified on purpose by punching the referee. After the match, Umaga, Vince, and McMahon all attacked Lashley. At Backlash in a Handicap match for the ECW title, McMahon along with his father and Umaga defeated Lashley for the ECW Championship. Vince gained the pin making him the ECW World Champion. At Judgment Day, Lashley faced McMahon, Vince, and Umaga again, in a rematch for the ECW World Championship. This time, Lashley won the match, but since he pinned McMahon rather than Vince, Vince remained the champion. At One Night Stand McMahon and Umaga tried to help Vince retain the ECW World title against Bobby Lashley, but failed when Lashley speared Vince and pinned him for the win.
On the taped edition of Raw that aired on September 3, McMahon, along with his mother Linda and his sister Stephanie, made appearances to confront Vince about his illegitimate child. McMahon then returned at Survivor Series to accompany Hornswoggle, alongside his father, in his match against The Great Khali. After that, he was only seen on WWE's pay per view, No Way Out 2008 talking to The Big Show after the latter had his nose legitimately broken by accident by Floyd Mayweather, Jr. before again not being seen until June 2008.
After the severe injury that Vince McMahon sustained on the June 23 episode of Raw, Shane requested for the Raw roster to stand together during what was a turbulent time. A sign fell on top of Mr. McMahon during his participation in the Million Dollar Mania sweepstakes. Shane's plea, however, was ignored and subsequently, Shane and his sister Stephanie urged the roster to show solidarity. On the July 28 episode of Raw, McMahon made an appearance to announce Mike Adamle as his and Stephanie's choice to be the new Raw General Manager. After Mike Adamle stepped down as General Manager, he and Stephanie became the interim on-screen authority figures for the Raw program. On the November 24 episode of Raw, Shane and Stephanie argued over who was in charge, leading to Stephanie telling him that Raw is her show. After being slapped by Stephanie, Shane finished the segment by telling her that from that day onwards, he was going to watch Stephanie run Raw "right into the ground".
At the start of 2009, Randy Orton began a feud with the McMahon family. On the January 19 episode of Raw, Orton punted Vince McMahon in the head, after he had tried to fire Orton from the company for previous comments made about his daughter Stephanie McMahon. The following week, Shane returned to television, leading him to attack Orton for his actions, turning face once again. On the February 2 episode of Raw, it was revealed that Orton challenged Shane to a No Holds Barred match at No Way Out, to which he accepted. At No Way Out, Orton defeated Shane in the match. The following night, Shane challenged Orton to an unsactioned match for that episode's main event. The match ended with Orton punting Shane in the head, as well as performing an RKO on Stephanie McMahon.
Shane returned on the March 30 episode of Raw, alongside Triple H and his father, to confront and attack The Legacy (Orton, Ted DiBiase, and Cody Rhodes). On the April 6 episode of Raw, it was announced that Shane would compete in a six-man tag team match against The Legacy at Backlash alongside Triple H and Batista, the latter of whom had returned from injury, where the stipulation was that if any member of Orton's team pinned any member of Triple H's team, Orton would win Triple H's WWE Championship; However, if any member of Orton's team was counted out or disqualified, Triple H would retain the title. On the May 4 episode of Raw, McMahon's character suffered a broken leg and ankle at the hands of Orton and Legacy as a way to write him out of the storyline.
Shane left the company on January 1, 2010.
On the February 22, 2016 episode of Raw, Vince McMahon presented the first ever "Vincent J. McMahon Legacy of Excellence" Award to his daughter Stephanie. As the award ceremony was taking place, Shane returned to WWE as a fan favorite to confront his father and sister in regards to the company's status. After Stephanie exited the ring, Vince and Shane discussed the status of Raw and how it was getting run down. Shane said he wanted to gain control of Raw (and essentially the company) to preserve it for future generations of the McMahon family. Vince made a deal with Shane that he will gain control of Raw if he would wrestle one more match at WrestleMania 32 and defeat his opponent; Shane accepted the offer, and Vince revealed that Shane would face The Undertaker in a Hell in a Cell match. On the March 14 edition of Raw, Shane had a confrontation with his father and The Undertaker, which concluded with him receiving a chokeslam from the latter. On April 3, at Wrestlemania 32, The Undertaker defeated Shane McMahon via pinfall after Shane tried an elbow drop on the Undertaker from the top of the cell, injuring himself in the process. The next night on Raw, on April 4, right after his father cut a promo on the stage, Shane came out and gave Vince a challenge to allow him to run that night's show so he can prove he can do the job, which Vince accepted. On the April 11 episode of Raw, McMahon was given control of the show for a second week via "popular demand on social media". He was again given control of the show for the third week running on April 18. Shane was given control of SmackDown for the first time in his career on April 21 in London. On the April 25 Raw, Stephanie McMahon returned to television and announced that their father, Vince, would officially declare who would run Monday Night Raw at Payback. At the event, Mr. McMahon announced that both Shane and Stephanie would jointly have control of Raw. On the July 11 episode of Raw, Vince would appoint Shane as the commissioner of SmackDown and Stephanie as the commissioner of Raw, before tasking them to name a general manager for their respective shows. The following week on Raw, Shane would appoint Daniel Bryan as the general manager of SmackDown. At SummerSlam, Brock Lesnar won his match against Randy Orton by technical knockout and continued to assault Orton as he was being tended to. Shane then confronted Lesnar, which resulted in Shane being attacked by Lesnar with a F-5. After the event, it was announced that Stephanie had fined Lesnar $500 for his attack on Shane, which Paul Heyman would pay off on the August 29 episode of Raw. On the August 30 episode of SmackDown, Shane would reveal during an interview that he was unhappy with how the situation was dealt with, as Heyman and Lesnar didn't take the punishment seriously.
On the November 8 episode of SmackDown, after Baron Corbin would suffer a storyline knee injury, Shane would ask Daniel Bryan to find someone to replace Corbin on Team SmackDown Live at Survivor Series. Later that night following the main event, after Shane would prevent AJ Styles, Bray Wyatt and Randy Orton from attacking Dean Ambrose, Bryan would ask Shane to be Corbin's replacement, which Shane would accept. At Survivor Series on November 20, Team SmackDown defeated Team Raw, during which McMahon suffered a legitimate concussion following a spear from Roman Reigns.