The Best Frank Caliendo Sports Moments

Frank Caliendo is one of the best impressionist comedians that I've ever seen.

Known for his hilarious impersonations of athletes, commentators and nearly everyone else in the sports world, Caliendo can be seen every weekend doing his bit and making fans laugh before hours of football watching.

And because the guy is so good at what he does, I figured I'd take a stab at some of his best acts—so enjoy, laugh and be ready to be amazed.

Gruden vs. Gruden

One of Caliendo’s most notorious impressions is that of former head football coach and Monday Night Football commentator, Jon Gruden.

Being spot on with the tone and delivery of Gruden’s voice and mannerisms, the comedian took things up a notch by having a conversation with Gruden himself, mocking the widely popular Gruden QB Camp that ESPN does leading up to the NFL draft.

Hilarity ensued.

How to Be an NFL Insider

Many of us sports fans wonder what it’s like to be an NFL Insider like Adam Schefter or John Clayton.

Well, Caliendo tackles the topic by mocking Schefter with this bit, which, as you can see, involves a lot of talking on the phone.

If you just listen to the video and not actually watch it, I guarantee you’ll think it’s Schefter himself talking. You would be wrong.

Richard Sherman's '30 for 30'

Who else but Caliendo can pull off multiple personalities and looks like Mike Ditka, Ron Jaworski, Jim Harbaugh, Chris Berman and Bill Belichick, among others?

One of the most hilarious sketches that the comedian has ever done, he mocks ESPN’s 30 for 30 by putting together this piece on the Seattle Seahawks’ Richard Sherman—which I really hope Sherman found was just as funny.

Frank Does Rome

There aren’t too many people more annoying in sports than Jim Rome, so when Caliendo takes on the task of impersonating him, he couldn’t have killed it any better.

Mixing in the usual Rome-isms and traits, Caliendo’s true talent comes out in this one—especially with the nonstop, four-syllable words that Rome always overemphasizes.

Mel Kiper Jr.

From the very beginning of this one, Caliendo does one of the best Mel Kiper Jr. impressions, the NFL draft guru of ESPN.

Shaking his head from the moment that Todd McShay opens his mouth to talk about Jarvis Jones, Caliendo must have studied a lot of film to perfect some of the epic battles that these two have when comparing prospects.

And then he adds in the intensity with which Kiper talks, which is just amazing.

Charles Barkley and Bill Walton

It always has to be hard whenever Caliendo is literally sitting across from the person that he is poking fun at with his impersonations—especially when it’s a Hall of Famer like Charles Barkley.

Rest assured, the guy holds his own, not only prerecording a piece for his former TV show, Frank TV, but then busting it out live, onset in front of Sir Charles, even making him laugh.

Coach Ditka

There are a lot of people who think that they can do a good impression of Mike Ditka, but Caliendo might be the only one who can actually pull it off.

Helping with a fake "Sports Science" bit on the Hall of Famer and current ESPN analyst, Caliendo mocks everything that Ditka is widely known for just beautifully, no doubt leaving the guy himself cracking up.

John Madden on Letterman

Arguably the character that made Caliendo known, his impression of former NFL head coach and color commentator John Madden is about as hilarious as you can get.

Mixing in the typical things Madden does—like open his mouth while his brain is still trying to process things—he could have easily convinced non-football fans who watched him on The Late Show with David Letterman that he was the real guy.

Stephen A. Smith

One of the loudest mouths in all of sports, ESPN’s Stephen A. Smith is notorious for putting emphasis on each and every one of his words and being as direct as possible.

So, naturally, that’s what Caliendo did while impersonating him, even making the real Stephen A. roll while listening to it—even though the comedian pokes fun at Smith adding words that few people are familiar with.

Morgan Freeman (LeBron James Redemption)

Can we all just stand up and applaud the guy on this one, because it is, no joke, Oscar-worthy.

Delivering LeBron James’ famous, “I’m Coming Home,” as actor Morgan Freeman had radio hosts Mike Greenberg and Mike Golic doing nothing but laughing because it’s so spot on.

Seriously, how does this guy do it?