‘Stephen Colbert’s Midnight Confessions’ Runs Hot in the Show, Cold in the Book

As a gigantic fan of Stephen Colbert, my confession is this: I thought his Midnight Confessions book pretty much sucked. I’m a Late Show diehard and have never missed an episode; I’ve been to a live taping; I track ongoing themes in his recurring bits and very much enjoy the “Midnight Confessions” segments on the show. So, what gives? Am I not the intended audience for this little toilet tank tome, which collects some of the beloved segment’s jokes in a beautifully fonted, nicely illustrated keepsake package? Why does this book fail me?

First there’s the matter of truthiness. “Truthiness” is an idea first proposed by Colbert on his old Comedy Central show, The Colbert Report, and it means that although something is factually untrue, it may still ring emotionally true and therefore sticks with us as “real”. Obviously, nobody expects the bulk of Colbert’s confessions to be factually true. But if they don’t resonate with that certain kind of pathos, which is what allows our identification with whatever frail part of our humanity the confession is predicated upon to produce the laughs that are our cathartic purge of this frailty, then the confessions are just jokes. They’re just two-liners with punchlines, and though the punchlines may never miss a beat, the selections in this book are on balance much less warm than the selections that appear on the show.

Reading the book cover to cover is a little like watching Peter Pan’s shadow run around the room. It’s amusing to look at the shadow’s hijinks, but much less satisfying than watching Peter try to attach the shadow back onto his own foot. Midnight Confessions is heavy on punchlines but comparatively weak on accessible human frailities.

Certainly, jokes that are performed will engage a different set of comedy tools than jokes that are on the page. On the stage, you have props. On the page, you have illustrations. This book’s illustrations are done by award-winning political cartoonist Sean Kelly, perhaps best known for his contributions to the New York Times Op-Ed page and the “Metropolitan Diary” column. His Midnight Confessions drawings properly enrich the punchlines provided by the text, but they simply cannot reinforce the content in a way that captures the emotion of the performances.

For example, if Colbert says he feels guilty about eating an entire canister of cake frosting, it’s one thing to look at an image of the demolished canister and it’s another thing to watch as Colbert shovels in several big mouthfuls while groaning with pleasure. The performance of eating the frosting unquestionably ups the emotional ante, prolongs our ability to appreciate the punchline by making the audience covetous of the frosting in ways the static image can’t accomplish. The performance of the confessions is often funnier than the text of the punchline or even the text plus accompanying imagery in the book.

Colbert is well-known for having a love of food and beverage. In the show’s first season, there were food options on the ultimately discarded “wheel of news” bit as well as interviews with people involved in the food industry or food-based non-profits, and Colbert’s remarks about his life at home were usually connected to food. By season two, a lot of that had fallen away and been replaced by the long-running “Hungry for Power Games” satirical primary campaign coverage where his Flickerman character had a champagne flute ever in hand, or simply by drinking a cocktail with an actor who was known to enjoy them.

As a sense of his enslavement to the Columbia Broadcasting System sunk in, laden with types of censorship that he was certainly unaccustomed to during his long run on Comedy Central, my own theory is that alcohol remains one of the most fertile territories for more adult-ish content available to Colbert now that his jokes must truly suffer scrutiny from the lawyers. As a result, you can see him genuinely savor that short glass of bourbon whenever it appears on screen.

Knowing how much he enjoys that bourbon aids in the viewers’ emotional investment. We have a lot of empathy for Colbert whenever he takes a sip. In the Midnight Confessions book, obviously, he can’t take that sip. So the book simply doesn’t include many of the food and beverage confessions even though these jokes are very close to Colbert’s true passions, one of the best ways of pushing back against the tone set by CBS, and some of the most recurring content of the confession bit. To not include these jokes means that the Midnight Confession actually isn’t a very good representative sample of the show’s bit. We should probably want the book to be a representative sample of the show’s bit, but it can’t be.

Instead, the book places a lot more emphasis on murderous feelings. Based on the confessions collected in the book, readers could generate a pretty long list of types of people that Colbert would like to die — people walking slowly in front of us on the sidewalk, people who sing “Don’t Stop Believin'” at karaoke, and so on. Readers could also generate an even longer secondary list of ways that Colbert enjoys intentionally putting people on tilt — inserting a few Skittles in the M&Ms bowl, aiming sneezes at people who didn’t say “bless you” the first time, and so on. We all recognize these people, but because we are not sociopaths, we generally do very little about them. These jokes hit so hard precisely because of our unwillingness to act; the jokes become our only defense and a way of acknowledging these people have broken some of the fine print of the social contract.

I’ve always felt that the excellence of this category of considerations would be better suited for a different bit on the show, and I think Colbert’s writers know it. The “what to do about annoying people” ideas generally end up funneled into The Late Show’s other major bit, “Big Furry Hat”. Colbert puts on a big furry hat, which he claims is something all dictators and divas have in common, then he goes up to the balcony of the set and pronounces the consequences these annoying people ought to receive. The confession bit and the hat bit are equally declarative in structure and they play with precisely the same type of content.

Their major contrast is that the hat bit is more empowering because it takes ownership of solutions, whereas the confession bit only takes ownership of guilty feelings while leaving solutions in the hands of God. Many of the jokes in the Midnight Confessions book may have had a stronger shelf life if they’d been funneled into a “Big Furry Hat” book instead. Therefore, far from making me feel hopeless about CBS shamefully cashing in on the success of The Late Show by flinging this somewhat watered down Midnight Confessions book our way just in time for no holiday season whatsoever, it clarified in my mind the prospect of a really excellent Big Furry Hat book. The ranting nature of that bit, its more proactive and energetic vibe, and the fact that it never relies on any props other than the easily illustratable hat itself, means that Colbert’s Big Furry Hat book could succeed pretty mightily where Midnight Confessions has not. Lest we forget, the hat bit indulges Colbert’s Catholicism just as much as the confession bit; it simply shifts focus from the quiet contemplation of the booth to the political noise of the pulpit.

There’s been no whispering among publicists whatsoever that such a book will one day exist. A lot of people are going to buy Midnight Confessions for the Colbert-lover in their lives. They should. It’s kind of silly and makes a good coffee table badge for devotees of The Late Show. Serious freaks like me who know the performed version of the bit inside and out already will not be pleased with it much at all by the time they turn the last page, but CBS will have made a pretty penny nonetheless and I think we ought to all be looking forward to the Big Furry Hat book to resolve some of the flaws in Midnight Confessions.

Meanwhile, to Stephen and the good people writing for The Late Show: I feel guilty about this negative review because I value the work that you do. I’m even grateful to CBS for the extent to which it’s allowing you to get away with it and of course giving you a bigger stage on which to stand. You deserve maybe seven percent of the blame for this book — the rest of it belongs to your corporate overlords. I hope this isn’t making sell-outs out of all of us. I hope you can forgive me enough to call and collect this bottle of bourbon I’ve got with all your names on it. Cheers.