McMahon eventually became the regular play-by-play commentator and maintained that role until November 1997, portraying himself as easily excited and over-the-top. In addition to matches, McMahon also hosted other WWF shows, and introduced WWF programming to TBS on Black Saturday, upon the WWF's acquisition of Georgia Championship Wrestling and its lucrative Saturday night timeslot (McMahon sold the timeslot to Jim Crockett Promotions after the move backfired on him and he eventually acquired JCP's successor company, World Championship Wrestling, from AOL Time Warner in 2001). At the 1987 Slammy Awards, McMahon performed in a musical number and sang the song "Stand Back". The campy "Stand Back" video has since resurfaced several times over the years as a running gag between McMahon and any face wrestler he is feuding with at that particular time, and was included on the 2006 McMahon DVD.
On the May 15 Raw, Triple H hit Shane with a sledgehammer meant for Michaels. The next week on Raw, Triple H had another chance to hit Michaels with the object but he instead whacked the Spirit Squad. For a few weeks, McMahon ignored Michaels and began a rivalry with Triple H by forcing him to join "Kiss My Ass Club" (Triple H hit McMahon with a Pedigree instead of joining the club) and pitting him in a gauntlet handicap match against the Spirit Squad. Michaels, however, saved Triple H and the two reformed D-Generation X (D-X). This led to a feud between the McMahons and D-X, throughout the following summer. He also with the Spirit Squad teaming with Shane lost to Eugene by disqualification on July 10. At SummerSlam in 2006, the McMahons lost to D-X in a tag team match despite interference by Umaga, Big Show, Finlay, Mr. Kennedy, and William Regal. The McMahons also allied themselves with the ECW World Champion Big Show. At Unforgiven, the McMahons teamed up with The Big Show in a Hell in a Cell match to take on D-X. Despite their 3-on-2 advantage, the McMahons lost again to D-X thus ending the rivalry.
As of 2006, McMahon has a $12 million penthouse in Manhattan, New York; a $40 million mansion in Greenwich, Connecticut; a $20 million vacation home; and a 47-foot sports yacht named Sexy Bitch. His wealth has been noted at $1.1 billion, backing up WWE's claim he was a billionaire for 2001, although he was reported to have since dropped off the list between 2002 and 2013. In 2014, McMahon had an estimated net worth of $1.2 billion. On May 16, 2014, McMahon's worth dropped to an estimated $750 million after his WWE stock fell $350 million due to a price drop following disappointing business outcomes. In 2015, McMahon returned to the list with an estimated worth of $1.2 billion. In 2018, his net worth reached $3.6 billion.
On February 1, 2006, McMahon was accused of sexual harassment by a worker at a tanning bar in Boca Raton, Florida. At first, the charge appeared to be discredited because McMahon was in Miami for the 2006 Royal Rumble at the time. It was soon clarified that the alleged incident was reported to police on the day of the Rumble, but actually took place the day before. On March 25, it was reported that no charges would be filed against McMahon as a result of the investigation.