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The 9 Funniest Sports Impressions

by: Penn Collins On  Saturday, March 21, 2015


The 9 Funniest Sports Impressions

Yesterday, a video went viral of Morgan Freeman reading LeBron James’ Decision II letter. Only it wasn’t Morgan Freeman. It was impressionist Frank Caliendo doing an impression of Morgan Freeman. Or maybe Caliendo was an impersonator doing an impersonation. I always get those two confused.

Frank Caliendo whether you find him funny or not, is pretty good at his craft, which is good, because few things are worse than a bad impression.

Caliendo’s video got us thinking about our favorite sports impressions. Yes, we know that Caliendo’s impression of Freeman wasn’t sports-related in and of itself, but rather, was a sports impression in that was a non-sports impression regarding a sports-based topic. We know it doesn’t quite add up, but we’re politely asking you to make the leap with us. This is hardly the biggest stretch we’ve made on these lists.

Here are the nine funniest sports impressions we’ve come across in our lives.

9. Caliendo’s Madden

Again, Frank Caliendo’s impressions may not be uproariously funny (unless you’re Terry Bradshaw or Howie Long), but they are so spot on that you’re able to find humor in the little tics and quirks in a character that you may not have even realized were there before. John Madden stammering over his words and catching his breath at the end of every sentence definitely qualifies.

8. Caroline Wozniacki’s Serena Williams

I didn’t understand all the cries of “racism” regarding Caroline Wozniacki’s half-assed impression of Serena Williams with giant boobs and an ass that went from the net to the serving line. Historically, these players make fun of each other during exhibition matches because you never really get to see players interact with one another in tennis, except maybe at press conferences. Was it distasteful? Maybe, but TONS of distasteful things are funny. But, then again, I might be the wrong guy to judge, as I’ve got a guy in blackface at #1. (Don’t worry, we’ll get there.)

7. Jamie Foxx’s Shaq

Shaq for President! Jamie Foxx lays down why Shaquile O’Neal would be an excellent president because he never loses his composure. While I won’t be giving my vote to any former Miami Heat players…ever, Foxx’s impression is pretty damn good, and we’ll see in the next few the intricacies of making fun of Shaquile O’Neal. We’ve got a couple of Shaqs on this list because he’s probably one of the most inherently funny-sounding athletes, and otherwise, this list would just be Frank Caliendo yelling at us nine times.

6. Jay Pharoah’s Shaq

Oh, man. This one is great. Jay Pharaoh, a comedian who is in pretty rare air when it comes to impressions, take his Shaq in the opposite direction as Jamie Foxx. Whereas Foxx showed him as unflappable and a little aloof, Pharaoh plays him with spastic eyes and a bobble head. I’m not sure that this is actually at all representative of what Shaq actually does, but this list is “funniest,” not “most accurate.” Look at him go…

5. DeAndre Jordan’s Charles Barkley

For some reason, last year, comedian Nick Kroll and a bunch of other comedians decided to conduct a table read of Space Jam. Why? Because it’s an awesome idea. They brought in NBA stars and comedians to fill all the roles. And while many of the stars didn’t bring a whole lot to the table, it should comes as no surprise that DeAndre Jordan was killing it as Charles Barkley. But it did comes as a surprise to most everyone at the table, including DeAndre himself, who kept cracking himself up, as though he had NO idea he could even do a Charles Barkley impression.

4. Kenan Thompson’s Charles Barkley

WHOA! WHOA!!!!! Slow down. We blew through the Barkley/Shaq skit paying so much attention to Jay Pharaoh and his Shaq that we didn’t get to take in and savor Kenan Thompson’s Charles Barkley. The only thing it doesn’t have going for it that DeAndre Jordan’s did was the element of surprise. We expect Kenan to take care of business, and he does. I wish I knew how to explain that voice that everyone uses to do Barkley. It sounds like a really old bicycle horn. And I mean that in the nicest way possible.

3.Drake’s Manny Pacquiao

Drake has quickly turned into hip-hop’s Neil Patrick Harris, singing and dancing his way through award shows to the delight of a middle America that would have never warmed up to hip-hop otherwise. And while much of Drake’s schtick is a little too cute, and this certainly would read that way on the surface, something about combining Drake, Manny Pacquiao, and “Let It Be” from Frozen all sort of works out into the perfect storm of comedy. The fact that Pac-Man has a real singing career forces this to ring a little more true than anyone would like to belivee it does.

2.Will Ferrell’s Harry Caray

Harry Caray seems to have been doing an impersonation of himself for most of his career, with the big glasses, the the endearing ramblings, and his unwavering love of Cubs over all other things in this universe. But Harry Caray didn’t do the best Harry Caray. Nope. That distinction goes to Will Ferrell, who appeared on SNL and the ESPYs as the disheveled anthropomorphic bobblehead.

But he begs an important questions: If you were a hot dog, would you eat yourself?

1. Jimmy Kimmel’s Karl Malone

Karl Malone? “Karl Malone.” Jimmy Kimmel, before he was a late-night personality, before he was on The Man Show, before he was even on Win Ben Stein’s Money, was a sports radio guy, and one of his big claims to fame was his drive-time Karl Malone impression. It basically consists of him mispronouncing words, sounding like he has a mouth full of marbles, and constantly referring to himself in the third person.

And it’s just about the funniest sports impression out there. Yes, he’s in blackface (I think), but you can’t very well do a convincing Karl Malone impression as a white guy, can you? Well, maybe. Someone get Frank Caliendo on the phone.