Will Colbert’s Anniversary Celebration Turn Into a Trump Roast?

On Tuesday night, Stephen Colbert is going to celebrate his 20th year in late-night television, and he plans to turn The Late Show into a reunion of The Daily Show: Jon Stewart, Samantha Bee, John Oliver, Ed Helms, and Rob Corddry are scheduled to appear. (What, no Steve Carell?) Given that Colbert, Bee, and Oliver are giving audiences some of the most ferocious critiques of the Trump administration, it seems inevitable that tonight’s Late Show will feature a lot of anti-Donald jokes. The present-day atmosphere is too grim to allow Colbert to simply hug some old friends and pat himself on the back for surviving (and thriving) for two decades of topical TV.

The timing of this is amazingly apt. Just last week, the FCC, in the person of Trump appointee Ajit Pai, said it was investigating complaints lodged against Colbert’s use of a vulgar phrase in a recent monologue. This is the same Pai who was the object of a withering attack on this past Sunday’s Last Week Tonight With John Oliver, in a piece the host did on the not-so-theoretical disintegration of net neutrality. Who would be surprised if Colbert and Oliver felt the need to test the patience of Chairman Pai and his agency one more time? And Bee, who has used the basic-cable precinct of TBS to launch her own hard-core political missiles at Trump, would seem likely to join in that low-flying fusillade.

Then too, Stewart — as the proud papa who birthed the careers of these other guests — has shown increasing itchiness to get back into the newsy-talk-show biz himself. Each time he’s appeared on Colbert’s Late Show, the running joke about him wanting to get behind Colbert’s desk and deliver his own Trump insults has seemed less and less like a joke and more like a fond, rekindling dream. On Tuesday night, all of Stewart’s TV kids may have to cower if Papa goes on a Trump tear of his own.

It’s still possible to think that, in a pre-Trump era, Colbert and this guest list might have sat around trading Daily Show war stories, with maybe an old clip or two thrown in for the sake of nostalgia. Now the atmosphere is more like the final days of Lenny Bruce, with comedians compulsively parsing the government’s definition of “obscenity.”

The FCC defines that concept as something that will “appeal to an average person’s prurient interest; depict or describe sexual conduct in a patently offensive way; and, taken as a whole, lack serious literary, artistic, political or scientific value.” Colbert’s roomy loophole would be that his joking has literary and artistic value — or at least that loophole would be roomy were the FCC being run by someone with a comprehension of artistic intent, an understanding that Pai, to judge by his public statements thus far, may lack.

Chances are no one’s going to get fined by the FCC after tonight’s Late Show, although why I’m confident enough to write that may suggest undue optimism on my part. There’s a part of me that wishes this reunion could just be a jolly, occasionally misty-eyed, politics-free affair. But most of me knows that not only is that unlikely, but also that jolliness and sentimentality cannot be indulged by any performer who’s making late night television with even the slightest awareness of what’s going on in the world outside. If you’re looking to escape all that, Jimmy Fallon is hosting Aziz Ansari and Blondie tonight.

The Late Show With Stephen Colbert airs weeknights at 11:35 p.m.

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