Bill Maher vs. Jon Stewart: Who’s a Better Keith Olbermann Replacement?

With Keith Olbermann gone, there remain only two gray-haired, left-leaning political pundits with a scathing wit and a captive audience. One of them will need to step up and lead left-wing media consumers into the 2012 elections. Who’s the better choice?

Not that either Maher nor Stewart will literally replace Olbermann—with NBC burned by Olbermann’s headstrong manner it’s unlikely they’d turn to Maher or Stewart, both lighting rods in their own right, to fill the void.

But with Olbermann gone from MSNBC, it’s likely that Maher or Stewart will be advanced in the public eye as next in line for the left’s go-to pundit. Olbermann had advanced past commentators like Chris Matthews who were at least as incisive and had greater experience, I believe, because of one reason—he had a sense of humor.

How else do you explain a former sports anchor ascending to the role of America’s most trusted left-leaning pundit over Matthews, a former Congressional staffer and presidential speech writer under Carter? For all the talk of “civility” these days, which at its worst seems to want to neuter all differences between the left and right, the left has shown itself to possess a distinguishing trait: it appreciates a good joke.

It’s no coincidence that the most significant show of public solidarity from the left since electing President Obama was a gigantic comedy act. Rachel Maddow and Chris Matthews might provide astute commentary and draw on the richest political knowledge, but there’s no way the two of them together could galvanize a crowd like the one at Stewart/Colbert’s Rally to Restore Sanity.

And yet, of the two Jon Stewart has shown himself in recent months to be the one capable of real influence. Colbert’s character humor is too constricting for people to really trust him to inform their perspective. What we’ve seen from the success of funny pundits is a paradox—we want them to mock (because there’s no other way through this stuff than to laugh) and at the same time, we want them to speak truth.

Bill Maher might not have the kind of nightly format that extends his audience to Stewart or Olbermann levels, but he certainly wields the influence of the paradox: he’s hilarious, but the astuteness of his “New Rules” segment sparks conversations after each of his Friday night shows.

It’s worth noting that Maher and Olbermann both criticized Jon Stewart’s Rally to Restore Sanity speech, wherein he suggested that both the left and the right share equally in political “insanity.” As Maher put it, Stewart’s argument “pretend[s] that the insanity is equally distributed in both parties.”

Especially in the wake of the Gabrielle Giffords shooting, the cries for “civility” have grown louder. It sounds good, but I fear this may result in Democrats appeasing ever more, while Republicans refuse to compromise an inch. They have a way of doing this. The New York Times reports today that Republicans had already started making the rounds on Sunday talk shows to undermine the arguments they anticipated Obama making in tomorrow’s State of the Union Address. As Maher puts it, “Republicans keep staking out a position that is further and further right, and then demand Democrats meet them in the middle, which is now not the middle anymore”—a position Olbermann echoed.

Jon Stewart’s ethos of equally-distributed culpability may continue to catch on with Democrats weary of incessant bickering. To be sure, he makes compelling points that are always spot-on and his magnanimous character is something to aspire to. But I think Democrats will find the other side won’t honor a truce flag if they stop fighting. Personally, I’d rather see the public turn to Bill Maher and stay embroiled in a fight for its values than follow Stewart’s call to lay down arms and get walked all over heading into the 2012 elections.

Tomorrow night’s State of the Union Address will give a pretty good indication of where the president is headed ideologically in this home stretch to the 2012 campaign. Where the public is headed ideologically is yet to be seen, but will surely take the form of whoever replaces Olbermann as the party’s go-to funny man.