For Charles Barkley, imitation is the highest form of flattery. But for the late John Madden, it was an offense worth contemplating legal action.
Barkley and Madden have both been frequently parodied by comedian Frank Caliendo over the years, but it was never mean-spirited. According to Barkley, who appeared on the latest episode of Barstool’s Spittin’ Chiclets podcast, he has no issue with being part of Caliendo’s comedic routine. But Barkley said Madden felt differently.
“I remember this phone call I got from my agent,” Barkley recalled. “He says, ‘Hey, John Madden wants to talk to you.’ He called me, I said, ‘Hey, you’re the best. It’s an honor and a privilege.’ He says, ‘Thank you…I want to talk to you about a lawsuit I’m thinking about filing on this a**hole Frank Caliendo.’”
“I’m like, ‘what?’ He says, ‘This ***hole, have you seen the impersonation he does? I hate it and I’m thinking about filing a lawsuit.’”
Barkley seemed to think the lawsuit was a harsh course of action and remembered asking Madden, “You don’t consider that flattering?” about Caliendo choosing to craft an impression of the NFL icon. “He’s like, ‘No! I don’t!’” Barkley recalled Madden saying back.
“And now I don’t want to insult John Madden,” Barkley continued on the Spittin’ Chiclets podcast. “I was like, ‘Well, I’ll tell you what, let me talk to my agent and my representation and I’ll get back to you.’ I never called him back.”
“I actually consider it flattering,” Barkley admitted of Caliendo’s impression. “I know Frank a little bit because he lives in Arizona. I’ve seen it in person, I’ve seen it on television, I think he does a fantastic job. But John was not having it. He was not having it at all.”
When Madden passed away in Dec. 2021, Caliendo tweeted about the loss, noting he didn’t know the NFL legend very well, but appreciated getting the opportunity to meet him at Super Bowl XLV in 2011. Caliendo has shared the story of that meeting several times, stating he did his impression in front of Madden’s grandkids.
According to Caliendo, after a few seconds of awkward silence, Madden said “I get it now” as he watched his grandkids laugh at the impression. But I’m not sure if Caliendo realized just how much disdain Madden initially had for being a staple of the comedian’s routine.

About Brandon Contes
Brandon Contes is a staff writer for Awful Announcing and The Comeback. He previously helped carve the sports vertical for Mediaite and spent more than three years with Barrett Sports Media. Send tips/comments/complaints to bcontes@thecomeback.com
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