A major facet of Adam McKay's comedy—from Anchorman to The Other Guys—seems to work like this: the expectation of a joke is set up due to a circumstance or more likely a series of anticipatory dialogs, only for the punchline to flounder, offering only a tepid payoff in exchange for the anticipation. Yet the audience laughs anyway, as much due to the mathematics of the routine—we anticipate a joke going here, so whatever goes here gets a modicum of automatic laughter, until we realize how actually funny or not the actual joke is—as it is due to the post-Seinfeld, now-Curb Your Enthusiasm era of American comedy we are living in, The Age of Awkwardness.
For McKay's films specifically, he isn't just prompting us to laugh at a space potentially devoid of humor, but also to laugh at a space where Will Ferrell (or a cohort) should be making a real, funny joke. Instead of making that "real" joke, the actor sort of ad-libs and we watch him fail or semi-fail to make a joke. That failure becomes the punchline. We watch the process of a comedian trying to be funny and failing, which is a sort-of-funny thing to watch.
This is meta-awkwardness; where in something like the UK The Office, or, in a more complicated scenario, the above mentioned Curb, the awkwardness comes from within the drama—the comedy comes from the awkwardness of the characters—in a film like The Other Guys, what's awkward is the awareness that we are watching an actor trying and failing to perform. Except that, to a degree, this effect is calculated—looking at McKay's other collaborations with Will Farrell, one can easily see that this is a style of comedy that the director-writer-actor combo like, whether or not one actually finds the technique amusing or consistent. (Does that make the "failure" actually a success?) This is certainly not new; one of the many things that make Jerry Lewis a master artist was his ability to tie into a real gag the transparency of his attempt at the gag, or his apparent awareness of a gag he is performing. Yet for Lewis, this was usually (at least towards the beginning of his career) an extra joke within an already funny joke, which deepened and expanded the range of the humor. What we have now (and perhaps in later Lewis as well) is the removal of a real joke in the first place, leaving just the comedian "floundering" as the joke. Does this mean that being a comedian no longer involves being funny but rather requires expertise at failing at being funny? Comedy as the comedy of the failure of comedy?