One of the most versatile actors to ever transcend their humble beginnings on Saturday Night Live, Will Ferrell went from being an integral part of the “Frat Pack” — the group of 90s comedians that often shared the screen together, mostly considered to include Ben Stiller, Jack Black, Owen and Luke Wilson, Vince Vaughn, and Ferrell — to an important part of 21st century comedy as a whole. It might seem like Ferrell owes his career to a sketch comedy show, but it’s obvious that he was always meant for something greater. According to the actor himself, Ferrell never wanted to be a comedian — he was always more interested in dramatic roles. This shows in many of his best films: he’s got real dramatic chops as well as the obviously impeccable comedic timing that has made him so famous. For this reason, his filmography is versatile as well as iconic. He might have a couple of flops under his belt, but there’s no denying that Ferrell has far more hits than misses.
The LEGO Movie
While it might just be a voice role (for most of the time, at least), Will Ferrell is fantastic in The LEGO Movie. He’s playing a bad guy — something he hasn’t really done very often — and he plays it so well. Named President Business (and eventually becoming Lord Business), the character is a commentary on the nature of conformity. Ferrell’s the perfect fit here, managing to stand out even among a cast full of other comedians.
Stranger Than Fiction.
Easily his best dramatic comedy to date, Stranger Than Fiction. wrestles with the nature of creativity and the burden that moving on can be for those who create. Will Ferrell plays Harold Crick, a man that author Karen Eiffel believed to be an object of her creation until he shows up at her door asking to be spared in her latest novel (she’d planned to kill him off at the end of it). It’s a whimsical and occasionally heavy film, and Will Ferrell perfectly toes the line between funny and fragile.
Anchorman
While it’s a little overexposed at this point nearly fifteen years after its initial release, you can’t have a compilation of Will Ferrell’s best roles without throwing in Anchorman: The Legend of Ron Burgundy (and its criminally underrated sequel, which some consider to be better and funnier than the original). The role is iconic for a reason: it’s a spot-on satire of many of the journalists we see on TV every day. It’s impossible to imagine the role being played by anyone else but him.
The Spoils series
An obscure little miniseries that aired on IFC between 2014 and 2015, The Spoils of Babylon and The Spoils Before Dying are two goofy satires of the movies from the 40s and 50s. Babylon covers melodrama and Before Dying covers noir, but both feature most of the same actors in different parts. Kristen Wiig and Will Ferrell definitely steal the show, though. Ferrell is transcendent whenever he’s given the freedom to just goof off, and The Spoils series is a great example of this.
Step Brothers
Speaking of getting the freedom to just goof off, Step Brothers ranks pretty high on the list of best Will Ferrell performances for this exact reason. Costarring alongside John C. Reilly, Ferrell and his new stepbrother are determined to hate each other… until their similarities eventually overpower their indignant attitudes and their bromance blooms.
Austin Powers: International Man of Mystery
The Austin Powers movies are definitely vehicles for Mike Myers first and foremost, but Will Ferrell’s supporting role in the first film is one for the ages. Again, the timing is impeccable here. His character is one-one, repeating the same gag throughout the movie, but that’s one of the funniest things about these films: they drag out bits, taking them from funny to unfunny to funnier than ever.
Megamind
Dreamworks often puts out animated movies vaguely similar to hit Disney/Pixar films, but Megamind actually proves to be better than just an Incredibles knockoff. Will Ferrell plays Megamind, a big, blue supervillain who actually succeeds in getting rid of his rival superhero. It’s a funny idea fulfilled to the greatest extent by an equally funny cast. The character actually draws a lot of parallels to Lord Business in The LEGO Movie, but to a lesser degree.
Zoolander
Another classic Will Ferrell film, Zoolander sees the comedian playing the ridiculously flamboyant and outrageously stupid Mugatu. The cast is great, with Ben Stiller and Owen Wilson playing nicely off of Ferrell’s no-holds-barred performance. The movie might be pretty hollow, but it looks a million times better based on the sheer failure of the sequel back in 2016.
Old School
One of the first instances of Will Ferrell scoring a leading role in an R-rated comedy, Old School is undoubtedly a Todd Phillips film (for better or worse). It starts out goofy and only gets goofier, but this works out well more often than not. Luke Wilson and Vince Vaughn are bringing their all, as is Will Ferrell.
The Other Guys
The first time Will Ferrell costarred in a comedy alongside Mark Wahlberg, The Other Guys is a throwback to the Will Ferrell comedies of the 2000s in the best way possible. It’s a buddy cop movie, but it doubles as a competent spoof of the genre. The action and the jokes are solid enough, but as always, the best moments come from Ferrell’s improv with the other comedians he’s sharing the scene with.
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