Howard Stern’s Most Chaotic Wrestling Interviews
According to multiple sources, The Howard Stern Show is set to be canceled once the King of All Media's contract with SiriusXM expires at the end of 2025.
Having ruled the airwaves for nearly 45 years, Howard Stern has hosted a litany of wrestlers on his iconic radio show. The host has placed countless performers in his hot seat, including Vince and Stephanie McMahon, Stone Cold Steve Austin and John Cena, getting all of them to open up about their personal lives in a way few interviewers could.
Over the decades, Stern has garnered praise for his monumental celebrity interviews, but he's also served as one of media's most controversial figures, often pushing his guests far beyond their comfort zones to create must-hear radio for his legions of fans.
In this list, we're breaking down the most chaotic interviews Stern has done with pro wrestlers, from grilling Triple H about his real-life infidelities shortly after he left Chyna to begin a romantic relationship Stephanie McMahon, to almost provoking a fight with Booker T thanks to inflammatory questions from sidekick Stuttering John.
Did your favorite Howard Stern Show moment make the list? Check out these chaotic moments from the Stern Show below.
- 1
Bret Hart
In 1999, Bret Hart joined the Stern Show for a career-spanning interview. The Hitman recalled his disdain for Vince McMahon during the appearance, recounting the moment he knocked McMahon out following the Montreal Screwjob.
- 2
Booker T
In this particularly contentious interview, Booker T sparred with Stern Show member Stuttering John in 2002.
Stuttering John had previously trolled Booker during a red carpet segment, nearly causing the five-time champ to throw hands at John. Booker T ultimately squashed the beef with Stern and his team, but not after a few heated exchanges.
- 3
Triple H
Having just left Chyna for his future wife, Stephanie McMahon, Triple H was put in the hot seat during this 2002 segment.
Stern dug deep into the details of Triple H's infidelity, which the wrestler unveiled with little-to-no hesitation. Chyna was never treated particularly well on Stern, this segment included.
- 4
Chris Kanyon vs. Ric Flair
Recently let go from WWE, Chris Kanyon appeared on Stern to accuse Vince McMahon of firing him for being gay.
On a subsequent Stern Show appearance, Kanyon was confronted by Ric Flair. "Chris has all the talent in the world," Flair began, "But Chris, you didn't have anything to give to the show right now and that's just the bottom line."
When asked if Kanyon could come back to WWE, Flair changed his tune. "This is Ric Flair telling you, you have not got the skills or the ability to be back in the WWE. You are not good enough right now to be on the show."
- 5
Chyna
It was clearly a difficult time in the life of Joanie Laurer. In 2005, Chyna dropped by Stern's studio to promote a reality show she'd filmed -- The Surreal Life.
Laurer showed up intoxicated, rambling incoherently for the majority of the interview. She later stripped off her clothes while cameras filmed, adding to the discomfort of this interview. This one is definitely NSFW.
- 6
The Iron Sheik
What a classic. The Iron Sheik was one of the greatest Stern guests ever, always bringing fireworks thanks to his hatred of Hulk Hogan and the Sheik's abuse of his sleazy manager.