Before McMahon became an on-screen character, he debuted as a color commentator. McMahon wanted to become a wrestler, but his father didn't allow him. After Ray Morgan's pay dispute, McMahon was asked to replace him as a commentator. McMahon was seen on live television a few times when he interviewed superstars in the ring or backstage.
Mr. McMahon and Feud with Stone Cold (1996-1999)
Mr. McMahon's character took the centre stage when Stone Cold hit him with a stunner. McMahon replaced Jack Tunney as the on-screen owner of the company. At Survivor Series, McMahon's character became a heel when he screwed Bret Hart. He transitioned into an on-screen personality and was replaced by Jim Ross on commentary.
Steve Austin was McMahon's biggest rival and often gave a stone-cold stunner to McMahon. The Austin-McMahon rivalry went on for two years as McMahon disliked Stone Cold and hated getting a stunner from him. McMahon tried his best to eliminate Austin and dethrone him as the WWF Champion.
He joined forces with The Rock and The Corporation to take down Austin and failed. During their rivalry, The Rock assisted McMahon to win the Royal Rumble match. He sent The Undertaker and Kane to fight Austin, but Austin prevailed.
McMahon's next rivalry was with The Ministry of Darkness, led by The Undertaker. Taker attacked Austin and McMahon and abducted Stephanie twice. McMahon joined forces with Austin. He turned on Austin and revealed himself as the leader of the whole group. At King of the Ring, Vince and Shane McMahon defeated Austin in a ladder match to gain full control of WWF.
After Austin defeated The Undertaker, McMahon was banned from WWF television for a while. In the fall of 1999, McMahon returned to television and won the WWF Championship. On RAW, he vacated the championship. McMahon spent a few months feuding with Triple H.
McMahon-Hemsley and Brand Extension (2000-2005)
After assisting The Rock to win the WWF Championship, McMahon turned on him at WrestleMania 2000 and aligned with Triple H. The McMahon-Helmsley Era began, and he sided with Triple H and Stephanie McMahon against Linda and Shane McMahon. McMahon began an extramarital affair with Trish Stratus, much to the disgust of his entire family. At WrestleMania X7, McMahon faced his son, Shane, and lost. After Mania, the alliance was dissolved. At the same night, Austin joined forces with McMahon and turned heel.
McMahon began a rivalry with the newly purchased WCW. On RAW, he found out Shane was the actual owner of the company. This led to WWF vs WCW. Team WWF faced Team Alliance at Survivor Series. McMahon turned face as the fans supported WWF. At the event, Team WWF won which ended the storyline.
In 2001, McMahon feuded with Ric Flair. He faced Flair at Royal Rumble, which he lost. Due to Flair being a co-owner, RAW and SmackDown were divided between Flair and McMahon. In June, McMahon defeated Flair to gain the sole proprietorship.
In 2003, McMahon began his rivalry with Hulk Hogan. At WrestleMania XIX, McMahon faced Hulk Hogan in a street fight and lost. McMahon feuded with Stephanie and The Undertaker in the same year and won.
DX and Donald Trump (2005-2007)
McMahon was not seen as an on-screen personality for over a year. In 2005, he feuded with Eric Bischoff as he was not doing a good job as a general manager on RAW. In 2006, McMahon began his rivalry with Shawn Michaels. At Royal Rumble, McMahon distracted Shawn, and Shane eliminated him from the rumble. At WrestleMania XXII, Vince McMahon lost to Shawn Michaels in a No Holds Barred Match. At Backlash, Vince and Shane McMahon defeated Shawn Michaels and God in a match.
On RAW, Triple H and Shawn Michaels reformed DX and feuded with Vince and Shane McMahon over the summer. At Unforgiven, the rivalry ended with DX emerging victorious over the McMahons. In 2007, McMahon began his rivalry with Donald Trump. McMahon chose Umaga and Trump chose Bobby Lashley to represent them at WrestleMania. At WrestleMania XXIII, Umaga lost to Lashley and McMahon got his head shaved. After Mania, McMahon feuded with Lashley and won the ECW title.
Various Feuds (2007-2012)
Between 2007-2008, McMahon had a smaller appearance as an on-screen personality and appeared on RAW where he made matches. He faked his death, ran an illegitimate son's storyline between 2007-2008. In 2009, he teamed up with Triple H and Shane McMahon to face The Legacy, which he won. After being assaulted by Randy Orton, they took McMahon off television.
In 2010, McMahon returned as a heel and began his rivalry with Bret Hart. At WrestleMania XXVI, Bret Hart faced Vince McMahon in a No Holds Barred Lumberjack match. The Hart family assisted Bret and McMahon tapped out.
In 2011, McMahon returned to RAW and addressed the concerns regarding CM Punk's contract. On RAW, Punk cut a promo on McMahon and the working of the company. At Money in the Bank, McMahon tried to screw Punk out of the championship match but was stopped by John Cena. McMahon showed up on a regular basis on RAW and fired Triple H as Chief Operating Officer. McMahon challenged Punk to a match, but he booked a match between Ryback and Punk.
The Authority and Sporadic Appearances (2013-2017)
After The Authority was formed, McMahon sided with the stable. McMahon would turn heel and cut a promo on face superstars such as John Cena and Roman Reigns. McMahon got superman punched by Roman Reigns on RAW during his WWE Championship match. In 2016, Shane returned on RAW and feuded with McMahon. McMahon set up a match between Shane and Undertaker at WrestleMania 32. After Mania, McMahon assigned Stephanie as the commissioner of RAW and Shane as the commissioner of SmackDown.
McMahon made sporadic returns to RAW, SmackDown, WrestleMania, SummerSlam, and Survivor Series. McMahon would change between heel and face during his promos. At RAW 25, McMahon turned on the crowd which led to Stone Cold confronting him. In the end, Stone Cold hit McMahon with a stunner.
Association with Theory (2021-present)
Around the time of the Survivor Series 2021, Vince McMahon got impressed by the young superstar Theory and started showing his support for him. He even manipulated scenarios to benefit Theory in the ring which helped the latter win the United States Championship and Money in the Bank briefcase as well.
He assisted Theory at WrestleMania 38 from the ringside for his match against Pat McAfee. Following Theory's defeat, McMahon faced McAfee and managed to beat him thanks to Theory's continuous interferences. This marked the first time McMahon won a match at WrestleMania.
Their celebration was cut-short when Stone Cold Steve Austin entered the ring and gave a stunner to everyone. On July 22nd, 2022, Vince McMahon announced his retirement at the age of 77 via twitter. It's unclear whether or not he would make any appearances going ahead.