Why Larry Wilmore’s Correspondents’ Dinner Speech Was Way, Way Better Than Obama’s

Over the weekend, US President Barack Obama delivered his eighth and final address to the annual White House Correspondents’ Dinner. Between his digs at Hillary Clinton, his description of Donald Trump as “the end of the Republic” and his already-iconic mic drop at the end, it’s safe to say he did pretty well.

Obama’s Correspondents’ Dinner addresses have been internet catnip ever since he took office. His easy delivery, deadpan tone and pop culture-conscious collaborations with comedians like Keegan Michael Key make for entertaining, funny watching, and the fact that it’s the President of the United States cracking jokes onstage adds an element of irreverence to what would otherwise be a pretty dull event.

But Obama’s performance last night was overshadowed by one from the man who introduced him. Larry Wilmore, the host of Comedy Central’s The Nightly Show and a former correspondent for The Daily Show under Jon Stewart, spent 20 minutes introducing the President, and in contrast to Obama’s well-received act, Wilmore’s routine went down like a lead balloon with the crowd of well-heeled, powerful politicians, journalists and celebrities who make up the typical Correspondents’ Dinner audience. Guests were later quoted as saying Wilmore “went too far” in his monologue, while many news outlets carried headlines claiming he’d “bombed” with the crowd.

And he had. His caustic one-liners about Obama’s use of drone strikes, the overwhelming whiteness of the crowd, American journalism’s many failings and Guantanamo Bay were met with stony silence, interspersed with booing.

But it’d be too easy to explain away the room’s frosty reaction to Wilmore’s jokes by blaming their subject matter. After all, at the 2010 Correspondents’ Dinner, a joke about drone strikes went down a treat. The only difference was that it was Obama himself making it.

Get it? It’s funny because, over his eight-year tenure, Obama’s killed an estimated 400 civilians in his vastly expanded drone strike program. A five-month long drone strike operation in Afghanistan last year caused “unintended deaths” in nine out of every 10 missions, and dozens of children number among the dead from strikes in Yemen and Pakistan, the youngest a one-year-old girl. Presumably that’s what Obama meant at the end of that gag, when he said: “You think I’m joking”.

So Wilmore’s cool reception comes down to something else, and the answer lies in the uncomfortably cosy relationship so many in the media have with the people they’re supposed to keep in check. For those not familiar with the Correspondents’ Dinner’s shtick, it’s a longstanding American political tradition where politicians and members of the nation’s most prestigious news outlets get together for an oh-so-jolly night of fun. It’s halfway between a roast and a high-school reunion, only if everyone in the room is either filthy rich or has access to nuclear launch codes. Here in Australia, the Canberra Press Gallery has its own version.

The Correspondents’ Dinner frequently attracts criticism for being the ultimate expression of the corrosive ‘insider’ mentality so many political journalists buy into: a willingness to let access, fame and proximity to power compromise the journalistic mission to hold those in charge accountable. It’s the same faux-respectable ‘establishment’ journalism that saw US media’s most prestigious names unquestioningly swallow George W Bush’s rationale for the war in Iraq, only to turn around and laugh with him about it a few years later.

In fact, the last time the crowd of media/political elites at the Correspondents’ Dinner responded with such hostility to an MC was in 2006, when Stephen Colbert delivered one of the great comedic performances of the 21st Century. Dripping with false flattery in his Colbert Report persona, Colbert delivered a scathing indictment of the war and the media who facilitated it.

As with Wilmore’s effort this year, he did it to a silent, squirming room.

Speaking directly to Bush about his recent appointment of a new White House Press Secretary, Colbert uttered one of the best summations of insider journalism there’s ever been: “I think I would’ve made a fabulous Press Secretary. I have nothing but contempt for these people.”

Last night, Wilmore attempted to do something in a similar vein — use humour to unsettle the powerful, even if it means losing the room.