Comedian Frank Caliendo Describes the Moment He and Oakland Raiders Head Coach Jon Gruden Met For the First Time (Exclusive)

Frank Caliendo is best known for his comedic acts and famous impressions of various celebrities like John Madden, Morgan Freeman, Adam Sandler and Barack Obama. However, there is one in particular from his humor-filled career in comedy that landed him a spot on HBO’s Hard Knocks.

Caliendo has become widely known for his Jon Gruden impression, so much so, he was invited to appear on the hit sports documentary series in its 14th season to impersonate the head coach of the Oakland Raiders right in front of him and the rest of the team. In an exclusive sit-down with PopCulture.com, the famous comedian described the moment that he Gruden came face-to-face for the first time.

“I think he didn’t know what to expect when he first met me,” Caliendo told PopCulture.com. “He was standing there with the coffee, he was like, ‘So you’re the guy that does me, huh?’ and I’m just like [makes Gruden face as he nods his head] and we did this for like two minutes each.”

Caliendo goes on to share what the meeting went like, adding: “He’s like, ‘Where you from?’ So I looked up where he was from [prior to meeting Gruden] … I was like, ‘Sandusky, Ohio.’ He’s like, ‘Really?’ I’m like, ‘No,’ and he’s like, ‘Good, ’cause you were blowing my mind, man,’” he added. “But he got into it.”

The clip of Caliendo on Hard Knocks starts off with him entering a room filled with the entire Raiders team, including Gruden.

“Excuse me, guys,” he says in his Gruden voice as he makes his way to the front of the room. “We got some s— to take care of right now, man. [Mike] Glennon, love you man. We needed a Quarterback on the team who had a lot of neck, we got a good guy for that one,” he said as the entire room erupts in laughter.

“Jon Gruden, University of Dayton, I do this s— for free. Know why? ‘Cause I f—ing love football. Knock on wood if you’re with me,” he continued as the camera switched over to show Gruden laughing.

While the former commentator and current head coach may be laughing now, he wasn’t as quick to laugh off Caliendo’s jokes. It took a minute for Gruden to warm up to what has become a fan-favorite impression. The Chicago native addressed why he believes it takes guys like Gruden and athletes in general, to be so accepting towards his sports personality impressions — even though he’s best known for his work in athletics, saying it’s simply a comfort thing for athletes. When someone is in their circle, it’s one thing, but coming in as an outsider, it takes some getting use to.

“A lot of times the sports people worry that it’s going to hurt their brand,” Caliendo confessed.

“But the sports people are always put on pedestals, even from when they were little kids, so it’s tough when somebody outside their world comes in and starts making fun of them” he added, even saying the comedians on Saturday Night Live deal with the same them when they do an impression of someone that maybe that person wasn’t fond of.

All of that said, Caliendo gets along great with the Raiders and Gruden, as well as, the Arizona Cardinals — a team he spends a lot of time with when he’s home and not traveling.

While the comedian may be well known for his involvement in sports, pop culture is a new world he’s branching off into as well. In fact, in his podcasts Al Jackson & Frank Caliendo Try To Be Serious and The Frank Caliendo-Cast, he touches on relevant topics going on with the world and in pop culture.

For more information on Frank Caliendo and his upcoming tour dates, visit his official website.