4. Step Brothers (2008)
Step Brothers is dumb, glorious fun. Its rushed third act, yes, is burdened by contrived dialogue that looks to wrap up the story in a respectable manner and ultimately isn’t as funny as the rest of the movie. But so much of Step Brothers is in fact Ferrell and Reilly bouncing off each other in perfect harmony, with Steenburgen and Jenkins excelling as the annoyed, serious parents. It has some of McKay’s all-time great scenes like Derek’s introduction, the bunk bed collapse, and the kid fight scene. And it somehow says more thematic resonance than his recent more serious fare.
Step Brothers really does have a message concerning the horror of growing up and the dread that comes with adulthood, in between licking dog crap and rubbing testicles on a drum set. It is the guilty pleasure type of comedy that McKay and Apatow utilized to change the comedic landscape in the 2000s, for better or worse.
3. Talladega Nights: The Ballad of Ricky Bobby (2006)
Talladega Nights is just a notch above Step Brothers in terms of quality. It is just a little more consistent all the way through, just a little more scenes that make you truly burst out laughing and is just a tad smarter. Talladega Nights is once again a Ferrell and Reilly show, it was the moment their dynamite chemistry became reliable box office gold and everyone around them does not miss a beat. From Gary Cole as Ricky’s uncaring father to Leslie Bib’s materialistic wife, each side player plays their role with absolute conviction.
It was the film where McKay feels most assured of the genius of his work’s own stupidity. Even something like Ferrell running around in his underwear actually gains quality and laughs the more you watch it, the more you bask in awe of the mind-numbing ridiculousness before you. And that’s not to say Talladega Nights is not smart in its comedy. The montage of Ricky’s rise is an exquisite way to introduce a character while being funny. Ricky’s paralysis scene expertly uses Rhames’s acting chops to make Ricky’s eventual self-stabbing all the funnier. And the dinner scene with the Ricky’s family is maybe the most tightly scripted, hilariously punchy dialogue scene McKay has written. And below the surface, one of the better critiques you will see of an Uber-Patriotic Bush America that, again, is delivered with more care than the venom McKay has spewed as of late. A 2000s comedy classic.
2. The Big Short (2015)
The Big Short marked a new phase in McKay’s career. Granted, the majority would rather have McKay retreat back to his previous style, but let no one forget just how The Big Short is. The Big Short is borderline addictive to watch. The standout scenes do not have you on the floor laughing but a scene like Jared Vannett’s pitch is just as mesmerizing as anything McKay has film. The script could go without the celebrity cameos, no doubt about it. But when megastars are not explaining concepts, they know nothing about to the audience, the screenplay is an expert blend of crass, pissed-off verbal battles and housing market word porn.
The film does not shy away from the ornate terminology and strategies surrounding the 2008 housing crisis and is all the better for it. And the film’s towering achievement is not losing both the gross inhumanity and occasional spark of humanity in this heartbreaking story. It manages to bring to light the callousness of the individuals that exploited regular Americans and also the complicated moral dilemmas people like Mark Baum found themselves in. Some people hate it. Some people love it. But, even at its worst, it did pave the way for Jeremy Strong and the reign of Succession.
1. Anchorman: The Legend of Ron Burgundy (2004)
There is something a little disheartening about a director’s first being their apex. Well, it would be if Anchorman were not an unapologetic riot from start to finish. Any deep dive into Anchorman inevitably transforms into recalling its greatest scenes. But how can it not when you got such legendary moments like the back-alley brawl.
Quite simply put, there is not a type of comedy Anchorman does not do well. The absurdist moments are always delightful departures from the main tone. The wordplay is unmatched. And multiple of the actors, specifically Ferrell, put on clinics for physical comedy. There is no secret sauce that makes Anchorman radically different and better than something like Step Brothers. It was just a singular production where nearly all of McKay’s jokes hit, and out came a pure comedy that rivals some of the best ever made.