In Honor of Will Ferrell Playing Baseball Today, The Top 9 Will Ferrell Roles

So in some of the coolest news ever, Will Ferrell is playing all nine positions in multiple spring trainings games today.

That shows how much the MLB cares about spring training games, eh? I mean it’s obviously a publicity stunt, but it’s a publicity stunt with a tremendous cause. Equipment used during his insane day will be auctioned off, with proceeds going to Cancer for College and Stand Up To Cancer.

Hot take:


That’s, AWESOME.

I fucking love Will Ferrell. He has his critics, but I think he’s one of the funniest actors I’ve ever seen. In my book, he doesn’t pass guys like Bill Murray or John Belushi, but you would have a solid argument if you said he was the funniest guy of this modern generation.

Which got me thinking: baseball, nine players, Will Ferrell, more than nine roles in movies or TV.

So then it became obvious: it is my pleasure, no, honor, no…DUTY, to rank his nine best characters. I wouldn’t be doing my job if I didn’t and I can’t miss these opportunities; you don’t get this put on a platter for you all the time.

So without further adieu, here’s Will Ferrell’s nine best roles. We’re talking best ongoing Saturday Night Live characters or movie roles that he pretty much carried himself. So no, no more cowbell, and the Bill Brasky skit isn’t in there because he had a lot of help in those skits.

9. Harry Caray, SNL


It’s only appropriate to put the Harry Caray impersonation in here, seeing as this revolves around him playing baseball. If you’ve ever had the pleasure of hearing Harry Caray spew liquid gold in the booth for the Chicago Cubs then you’d know that this impersonation is extremely accurate. The drunkenness (with shout outs to Budweiser), the rambling, the non sequitur, the shaking, the voice, all spot on. There were a few SNL skits with him playing Caray, but the one about outer space is by far the best one; that skit is why they call him whiskers. And to boot, I’d eat the moon if it were made of spare ribs too.

8. Alex Trebek, SNL

This is an awesome impersonation of Trebek, but the interactions with Sean Connery on Celebrity Jeopardy alone make this a worthy pick. The flustered looks he gives are awesome, and the patronizing and critical comments are gold. However, it’s certainly not his best. There’s clearly better choices, although it is great. Shit, Burt Reynolds/Turd Ferguson is probably the funniest character on that skit, but Will’s still pretty good nevertheless.

7. James Lipton, SNL

This isn’t Will doing wild and crazy shit but rather being an expert at impersonations, again. He gets the artsy fartsy douche canoe that is James Lipton spot on, and it pays off in dividends. You don’t even have to know about Inside the Actor’s Studio to laugh your ass off with his ridiculous questions and exaggerations along with his weird ass chuckles. And the questioner at the end with the French name, amazing. The one with Kate Hudson as Drew Barrymore and he falls backwards is tremendous, but his best one is the one with Alec Baldwin as Charles Nelson Reilly. “It is a deliiighttttt.”

6. Frank “The Tank” Ricard, Old School


It’s not a character that requires a whole lot of skill; this is just Will being Will. The thing that makes him so great is that, like a lot of other Ferrell characters, he’s just so fuckin’ quotable!

“You tell anyone about this and I’ll fucking kill you. I’m kidding, I’m kidding, we’ll have him home by tonight.”

“You know I was thinking we could go back home, have some dinner and pop in the Sisqo CD, no?”

“Actually a pretty nice little Saturday, we’re going to go to Home Depot. Yeah, buy some wallpaper, maybe get some flooring, stuff like that. Maybe Bed, Bath, & Beyond, I don’t know, I don’t know if we’ll have enough time.”

“Blue! Why is there no ice in my lemonade?!”


“I like you, but you’re crazy!”

“You’re my boy Blue!”

And, of course, “WE’RE GOING STREAKING!!!!!”

Maybe not his best character but one that, when he’s brought up, you say, “Oh yeah, he’s hilarious in that.”

5. Allen Gamble, The Other Guys

This is, possibly, the most underrated comedy movie. Ever. Not just for Will, just ever. It’s amazing if you haven’t seen it. Will does a lot of goofy shit, but it’s more witty, smart humor. The whole bit with the Little River Band and any other interaction with Mark Whalberg is amazingly written in this film. It’s also, sneakily, extremely quotable. A solid performance from start to finish from Ferrell. It’s so awesome, and sadly, not as many people as seen it. It deserves so much more love, so I’m giving it some here. DESK POP!

4. Buddy the Elf, Elf

“Buddy the Elf, what’s your favorite color?”

Buddy is the festive voice of our generation. For our parents, it’s Ralphie from A Christmas Story or any of those classic claymation characters (alliteration like you read about), and for us it’s Buddy. Just the kid in all of us coming out. So quotable, especially during the holiday season, but the reason why I put him lower is because it’s just outside of the fringe of him at his best. This is him at his really good, but it’s not a movie where he is pee-yourself-laughing-every-time. Maybe it’s because he can’t swear or anything like that, but it’s not top 3 material for me.

3. Brennan Huff, Step Brothers

Literally the exact opposite character than Buddy. One’s proactive, adventurous, kind hearted, and just a jolly dude, and the other is lazy, dirty, and just an asshole. And you know what? I’m alright with that. Step Brothers is the funniest movie ever, I’ll stand by that, and the STUPID humor from Will Ferrell and company is the reason why. It’s just soooo ridiculous that you can’t help but die from laughter. Also an incredibly quotable movie, but I don’t want this to be a 500 page essay so I’ll refrain from going hard. He’s so stupid but so vulgar in it; it doesn’t have to be sophisticated humor, which is what, accidentally or not, makes him and that movie genius.


2. Ron Burgundy, Anchorman Series


Yeah, yeah, I’m sure everyone was expecting this to be #1, but listen: it’s hilarious, yes, it’s quoteable, yes, and it’s certainly a mixture of different types of humor, but the Ron Burgundy character is tainted by the sequel. Yeah, maybe it’s a little unfair, but his whole Burgundy bit got a liiiiiiiiiiittle overplayed. If the sequel wasn’t shoved down our throats and force-fed to us, or preferably if the sequel just didn’t happen at all, then maybe Ron would be the “classy” #1 overall.

And maybe that speaks to his original performance even more: the fact that it was strong enough that, even after that second movie, he’s still #2 shows how funny he was. But I dunno, whenever he did more with characters on things like SNL he killed it every single time. With Ron, not so much. Don’t get me wrong: he’s amazing, but Ron Burgundy isn’t that amazing.

Doesn’t help that he told a whole city to go fuck themselves, but still.

1. George W. Bush, SNL

Again, just an amazing impression from top to bottom. From the voice to the eye squinting, he gets every little niche about W. down to a T (see what I did there?). And it’s great because it’s everything you want in a Will Ferrell character: goofy, out of nowhere shit, smart, witty humor, quick humor, playing off of other people, and in this case, a perfect mimic of our 43rd Commander-in-chief. I think a lot of people forget some of those highlights from the W. skits on SNL: “Strategery” became a huge thing in the political world and guys like Rush Limbaugh still use that term today. There’s no real flaws in any of his performances has George W. Bush, and there’s certainly a lot of them.

“Being a leader blogger is full of tough decisions. That’s why I’m going with the chimichanga George W. Bush impersonation.”

I’ll leave you with, maybe, Ferrell’s best skit as W.