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How Stephen Colbert Won Cable, Lost The Presidency, Scared Bears, And Went Out On Top (And So Can You!)

All good things must end. There is a season, turn, turn, turn. Hold me close, tiny dancer. Okay, yeah, that last one doesn’t really work.

How Stephen Colbert Won Cable, Lost The Presidency, Scared Bears, And Went Out On Top (And So Can You!)
[Photo: Scott Gries, PictureGroup, courtesy of Comedy Central]

Barring a last-minute reprieve from the governor, by midnight on the Eighteenth Day of December in the Year of Our Lord Two Thousand and Fourteen, Stephen Colbert will be no more. After nine years on Comedy Central, the blustery six-time Emmy Award-winning perma-outraged blowhard of late night news commentary will die for the sins of our polarized culture of biased news and backbiting commentary. That is, he’s going to host a different show. Tomorrow, the “t” in “report” will once again be restored to its hard consonant glory and the name and lacquered visage of Stephen Colbert will disappear into obscurity, never to be seen again.

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By which we mean mid-next year, when the actor portraying Stephen Colbert will replace David Letterman as host of CBS’s Late Show. (Confusingly, that actor’s name is also Stephen Colbert, his IMDB page listing small roles in Law & Order: Criminal Intent, Bewitched, and The Hobbit: The Desolation of Smaug. For the sake of clarity, I’ll refer to both as Colbert, but will only mean one or the other, sometimes both, but never neither.) However Colbert decides to go out in his final episode—smash cut to black like Tony Soprano; waking up next to Jerri Blank, like Bob Newhart did with Suzanne Pleshette; heartfelt wave from a helicopter like Richard Nixon—one thing is clear: He’ll be going out on top.

It was a near-perfect nine-year run for The Colbert Report, taking Colbert from eyebrow-cocking Daily Show correspondent to leader of his own Nation, best-selling author (and authors’ rights advocate), restorer of sanity and/or fear, presidential candidate (in South Carolina), sponsor of the U.S. Olympic speed skating team, savior of Christmas, and enemy of godless killing machines (aka, bears). Leaving short of a decade saves him from the drawn-out embarrassment of once-loved institutions that lasted too long, like the Bush dynasty (three terms combined with the possibility of more), Saturday Night Live (40 up-and-down seasons and counting) or the Roman Empire (whose last few hundred years were a bloody mess). It also lets him keep all his money, like when Tom Cruise dumped Nicole Kidman just before their marriage lasted a full decade.

Getting out while the getting’s good is only one of the valuable lessons you can learn from Colbert and apply to your own late-night career or your sideline in Mr. Goodwrench and pistachio marketing. Here are a few more.

Modesty Is For Losers (And Democrats)

When he debuted in October 2005, Colbert told his audience that he had “a lot to do tonight, a whole big world to fix.” Watching the clip, you can hear that they barely tittered. No one knew that Colbert was completely serious—he would try to use his little Comedy Central show to fix the whole big world. Look no further than the series of episodes he did from military bases in Iraq in 2009 (when the war had dragged on for six years and threatened to drag on longer than SNL and be just as ignored) or the work he’s done for school kids with DonorsChoose.org. And then there’s that aforementioned Rally to Restore Sanity and/or Fear, which Colbert organized with Jon Stewart, which did… something! Colbert never thought small and he never constrained his ambition. You shouldn’t either.

Speak Truthiness To Poweriness

Jokes aside, Colbert was genuinely brave and totally subversive in 2006 when he performed 24 minutes of biting political commentary as comedy in front of President George W. Bush at the White House Correspondents’ Association Dinner. Standing there at “Nerd Prom,” the glad-handing-est night of the year for the press and presidency, Colbert dared to say things like, “So, the White House has personnel changes and then you write, ‘Oh, they’re just rearranging the deck chairs on the Titanic.’ First of all, that is a terrible metaphor. This administration is not sinking. This administration is soaring! If anything, they are rearranging the deck chairs on the Hindenburg!” (Luckily Bush’s boss, Dick Cheney, was in an undisclosed location that night or there would’ve been hell to pay.)

Colbert was criticized from the left and the right, but Colbert never backed down. Throughout his nine-year run, Colbert has never kissed a ring or an ass, especially if it was an ass wearing a ring. Never curry favor; always speak the truth.

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Don’t Just Embrace Social Media, Look It In The Eyes, Hold It Tenderly In Your Arms, And Make Sweet, Sweet Love To It

Every morning, when his show isn’t on one of its many generous breaks (seriously, Colbert’s staff must celebrate every holiday, even the obscure ones like Yom Kippur and Presidents Day), @stephenathome tweets to his 7.25 million followers, “Last night’s show, my best yet.”

This is just one of the many clever meta-jokes Colbert makes on social media. Colbert is very much a creature of our multi-screen, wireless present. Whether he’s editing a Wikipedia entry about elephants on air (causing consternation within the crowdsourced site’s community), rallying his nation to name a bridge in Hungary after him in an online poll, or trying desperately to make his ’80s synth-pop stalking anthem “Charlene (I’m Right Behind You)” a viral sensation, Colbert showed a native fluency in the language of the web. Colbert’s friend and rival Jimmy Fallon has clearly learned a thing or two from him, turning The Tonight Show into a collection of viral videos. Mastering the tools of the moment—Twitter, Snapchat, Ello (remember Ello!?)—will make you nimble and help you kick Jimmy Fallon’s skinny ass. (Spiritually, if not ratingsly.)

Even Stars Need To Play Second Fiddle

His show may be named for him and his studio may sport a “C”-shaped desk, an oil portrait of himself standing in front of an oil portrait of himself, and his own name emblazoned in lights, but when it matters most, Colbert knows when to step back and let his guests shine. Before he gets into character as Stephen Colbert, the right wing bloviator, Stephen Colbert the performer and producer tells his guests (many of whom are journalists and authors who rarely get to appear on television), “’Hey … I do the show in character, and he’s an idiot, and he’s willfully ignorant of what you know and care about. Please just honestly disabuse me of my ignorance. Don’t let me put words in your mouth, and we’ll have a great time out there.”

While his interview segments are characterized by such ignorance and tetchiness, most guests come off looking the best they ever have. Colbert, whose background is in improvisation, knows that the key to a great performance is collaborating, not showboating. Give everything you have to your partner and you’ll get so much more in return.

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In The End, You Gotta Be Yourself

Stephen Colbert spent the last nine years in disguise, or as Vanity Fair put it “In The Irony Mask.” Tougher still, his disguise bore his own name and his own face: He was hiding in plain sight. During that time he gave a number of out-of-character interviews, but he also did things like testify before Congress in character, which seems like it would have violated all kinds of contempt laws.

Starting tomorrow—but in a big way in 2015—Stephen Colbert is going to have to introduce the world to Stephen Colbert, real person. It’s hard to be yourself, especially when the world loves the utterly phony persona you’ve put forth for much of your professional life, but you’ll never get ahead unless you finally embrace honesty and do the hard work of being you. People may not laugh at you as much, but when they do you’ll know it’s because of you, and not because of some meticulously constructed character. The new year is almost here. Do what Stephen Colbert did and drop the act already. Your real fans will stick with you no matter what.

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