Kurt Angle found it financially challenging as he was unable to maintain a serious demeanor while filming segments with Vince McMahon. The segments, which took place in 2001, frequently featured Angles, McMahon, and Steve Austin interacting together, exchanging gifts, and even singing.
On a recent episode of the “Notsam Wrestling” podcast, Angle remembered how he repeatedly lost his composure during the filming of these laugh-out-loud segments, prompting a stern rebuke from McMahon. He recalled McMahon saying,
“Vince (McMahon) said, ‘Hey, we’re going to do these pre-tapes, but last week was a disaster because you guys kept breaking characters. You guys kept laughing. So, this week, if you break character, you get fined ,000.’ So, I got fined ,000 because I broke character four different times. I started getting serious. I was like, ‘I can’t do that anymore, I’m going to lose all my money.’ So, I wouldn’t break character anymore, I don’t know how I was able to do it.”
The fun-filled skits ended when Austin turned against the WWF to join The Alliance in that same year’s InVasion pay-per-view event.
Later, Angle also joined The Alliance but surprised everyone by turning out to be an undercover agent for the WWF. This was revealed at Survivor Series 2001, when the WWF triumphed over The Alliance.