Emmy Drama: What Will Happen If Conan Wins?

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It might seem unlikely that Conan O’Brien will walk away with an Emmy Sunday night for his short-lived stint atop The Tonight Show, but surely no more unlikely than the fact that he received a nomination in the first place. And if he were to indeed win and hop up on stage to accept his honor, the Hollywood Reporter Esquire Blog is quick to note, it could prove to be one of the most awkward, bizarre and unpredictable moments in Emmy history. Why? Because his settlement deal with NBC – which includes strict wording about refraining from making any “disparaging” comments about the network or top brass – remains in effect until next Sept. 1. That’s next Wednesday. So how might Conan wiggle his way around the agreement?

Did ‘who-cares-it’s-August’ TV just become must-see TV?

Now granted, I’m just speaking for myself – the TV novice. I know that TV experts like Jim love to debate the annual Emmy dance. But I think the most compelling storyline of this year’s awards is the battle for the “Variety, Music or Comedy Series” honor, where The Tonight Show With Conan O’Brien is the only late-night show nominated from a major network. He squares off against Saturday Night Live, The Daily Show, The Colbert Report and Real Time With Bill Maher. I would pick Daily Show from that roster – for its invaluable contextualizing of these bleak, bleak times – but being a proud member of Team Coco, I’d also be just fine with the awards body sending a strong message to NBC, that they’ve forsaken their late-night future in kowtowing to Jay Leno.

If we take as a given that Conan has a fair shot at taking home a prize Sunday, the far more interesting question then becomes: What can he – and will he – say? As THR notes, the Emmys will mark one of the first times since the Tonight Show handover that Conan shares the room with his former bosses. And parsing the language of the agreement signed at the end of O’Brien’s Tonight Show run, THR says Conan’s settlement deal defines “disparaging comments” as anything that’s “false” and anything that would be considered too “insulting or defamatory.” This means that Conan could be in big trouble if he says anything that’s false and mean.

But apparently, if what he says is true, Conan O’Brien is in the clear.

So there appears to be a legal loophole that Conan can work with. But now we arrive at the real question: Would he really want to? Among a few TV fans here in the TIME offices, we’re divided in our opinions. I think Conan has demonstrated, a couple times now (see below), his desire to call out NBC for treating him like an afterthought. In this 60 Minutes interview, he manages to suggest that he thinks he was unfairly pulled off his show, that Jay Leno acted dishonorably, and that the NBC execs he trusted did him wrong:

[youtube=http://www.youtube.com/watch?v=Of3b0DYxDtY]

Note at 2:37: “You know at some point, I’m sure I’m going to bump into these people.” By “some point” he means tonight. While nominated for a program that aired on their network. A program they fired him from. How would an acceptance speech not be sweet justice?

This said, some of my esteemed colleagues think he’s too much of a class act to lambast the network on primetime television. They see him making a short and gracious speech, and stepping down.

But given the Team Coco love that has flooded the Internet – “I’m With Coco” has more than a million fans on Facebook, and O’Brien tweets out daily to almost 1.5 million Twitter followers – there are plenty of people hoping that O’Brien rises triumphantly at the end of this embarrassing affair, looks down on those who made him a fool, and exorcises his demons right up there on the Emmy stage, settling the score in front of a worldwide audience.

Now I doubt anything that explicit will happen. After all, David Letterman and Jimmy Kimmel have been inflicting more than enough damage on Conan’s behalf – Kimmel did it to Leno’s face, no less – and Conan seems to prefer the nuanced approach of poetically worded one-liners. But an Emmy win Sunday night could be a big, big deal for his fans, his new network, and the ratings of his new show. More than that: It might give those old bosses in the audience just a fleeting second’s pause, wondering if they made a colossal mistake.

So what will it be: Subtle or overt? Sweet or scornful? Is revenge best served up cold, or red hot?

[youtube=http://www.youtube.com/watch?v=axwO6BkCtIo]