At this point in his career, Will Ferrell needs no introduction. He is always one of the funniest aspects of whatever project he’s taking part in. That said, receiving no introduction could be considered his bread and butter, because when you don’t see him coming it often elicits the biggest laughs. Keeping that in mind, we decided to browse his body of work for the most memorable and hilarious times he’s appeared out of nowhere, counting down his ten best. (Editor’s note: Click on the show titles for video clips.)
Ferrell’s cameo as the speed-addicted Dave, whom the lead characters pay to write college essays for them, is certainly not without its charms. Of course, while his performance here is certainly worthy of a few chuckles (and the number 10 spot on our list), it never quite hits the heights of hilarity you might expect, especially considering the circumstances. We know he can’t just resort to crazy yelling every time he needs a laugh, but if he’d played the part a little less tame, there is no way this appearance wouldn’t have been bumped up a few spots.
You couldn’t ask for a better setup when it comes to a Will Ferrell cameo than plummeting to his death with a bum parachute surrounded by dildos dressed as Abe Lincoln. On description alone, his cameo as deceased car dealer McDermott warrants a spot on this list. Unfortunately, the key to a great cameo is knowing when to quit, and Ferrell’s reappearance as an angel towards the end of the film just doesn’t stack up to what had already come before. Funny as he is, sometimes too much of a good thing can turn out not so good.
There are odd cameos for comedic actors, and then there’s this appearance as newcomer attorney Larry Flood on the season 2 finale of the CBS law drama “The Guardian.” We already know what you’re thinking: If it’s a drama cameo, then how does it qualify for this list? Quite honestly, he is so out of place here that you can’t help but laugh. Bonus points go to Ferrell for playing the part so straight and chipper the entire time, only to be unceremoniously shot in the head and killed by the end of the episode. A cameo so strange it has to be seen to be believed, we have no qualms granting it a place on our list.
We know that the comedic stylings of Tim Heidecker and Eric Wareheim are certainly not everyone’s cup of tea, which is why putting this cameo any higher on the list would be ludicrous. However, this is exactly the type of manic humor Ferrell excels at, so putting it any lower would also make no sense. Tim and Eric sketches have a tendency to become funnier the more you watch them, and Ferrell’s portrayal of clown outlet owner Donald Mahanahan here is no exception, especially when you consider the striking similarity to a certain Chicago Cubs announcer heard at the very start of the sketch.
Look, we all know “The Internship” sucked. Hell, none of us probably even needed to see it to agree on that, which makes Ferrell’s cameo as Kevin the mattress salesman that much more satisfying. That is to say, that much more satisfying due to how surprisingly funny it actually is. Any time Ferrell straps into the role of an inept jerk, you simply must expect laughs. Luckily, even in a low quality film such as this one, he brings gold. And unlike the situation with “The Goods,” his later appearance in an extended scene lives up to its predecessor.
Things took a turn for the weird and generally unfunny when the character of Ashley Schaeffer reemerged during several episodes of HBO’s third season of “Eastbound & Down,” but his initial appearance in season one was equal parts surprising and gut-busting. More than that, it also brought a slew of outtakes, and nothing says the actors were having a great time being funny more than that. Although Schaeffer may have overstepped his bounds by the end, the laughs still heavily outweighed the groans, leaving our memories of the character in good standing.
The Mustafa character played by Ferrell in the first two Austin Powers films is a great example of a cameo appearance done right. Not only is the joke hilarious the first time around, but it is changed up just enough in round two to keep it fresh. In fact, Ferrell’s scene in the sequel is arguably funnier than the original. Best of all, he didn’t come back for the third installment, ending the character’s run on a high note — unlike the franchise itself.
Easily the funniest name given to any of Ferrell’s characters, Deangelo Vickers was introduced in the best way possible as the new replacement for Michael Scott. Not only was he utterly incompetent, but his flaws as a person were truly bizarre and hysterical. While many would consider four episodes more than a cameo or small role, it was four out of nearly two hundred, so we had to make an exception. Besides, the fact that he brought so many laughs in such a small amount of time simply can’t be ignored.
We will probably catch a lot of flack for putting THE Chazz Reinhold in the number two spot instead of crowning him the obvious victor, but the element of surprise is ultimately what will win out our list. Don’t get us wrong, this is easily one of the most iconic roles Ferrell has ever played in one of his films. And considering the relatively small amount of screen time he is given, that feat is all the more impressive. In the end, however, if you’d been paying attention to his career at the time, a very similar reveal had been done only a year prior with another character of Ferrell’s…
Many either knock this film for not being any good or simply haven’t given it the time of day, but we assure you everyone — especially Ferrell — are at the top of their games here. Prison inmate Big Earl feels like an amalgam of just about every character Ferrell has played over the years, and the results of such a mixture are predictably side-splitting. We’re not gonna lie, his scenes with Ben Stiller and Owen Wilson get weird, but it’s the kind of weird that gets you laughing just thinking about it, even if it’s been a while since you saw the movie. And you’ll certainly never think of dragons the same way again.
