Being on ‘The Daily Show With Jon Stewart’

Several years ago when I told my wife Francesca that instead of looking for a job (I was freelancing, which is to say underemployed), I should write a book on presidential speechwriters, she looked more than a little alarmed but said with great equanimity: OK, if you that’s what you think you should do, then you should do it. (This is characteristic, by the way, of why my wife is awesome.) Then she added one condition: But you have to get on “The Daily Show.”

Flash forward three years to the spring of 2008 and the publication of my tome, “White House Ghosts: Presidents and Their Speechwriters.” (It’s a fun read and makes a great Valentine’s Day present.) I had told the Simon & Schuster publicist of my “Daily Show” quest and to my great delight she came through. I can forevermore say that Jon Stewart saved my marriage.

You can watch my appearance at the bottom. Here is an account I wrote about it on my now defunct personal blog. It gives a small insight into what it’s like to be on the show and what Stewart is like backstage. (Spoiler alert: He’s exactly the same.)

NEW YORK – First there’s the green room, which is of course not green, though it has my name outside it. It’s a narrow but comfortable room with a flatscreen TV, assorted refreshments (including Red Bull — who the hell needs to get more charged up before going on the Daily Show?), a bowl of candy, a couch and a couple of chairs. Katie the publicist is already there as Fran, Mom and I walk in. I dig the last piece of Starburst out of the candy bowl. Fran grazes from it, nerves driving her to chocolate.

Hilary the producer pops in to say hi, give the schedule. My half-dozen friends and family who were given golden tickets have presumably been sitting in the theater for over an hour — what are they up to? (I later find out that a stand-up comedian does a complete set to warm up the crowd.)

Makeup. The woman has been with the show from the start – back to the Craig Kilborn days. She says I’ll be fine. I’m nervous.

I’m pacing. Back in the green room. It’s half nervous energy and half energy-maintenance. Back and forth. Forth and back. Katie, Fran and Mom are seated, watching me bop back and forth. We’re making small talk though for the life of me I cannot now recollect it.

It’s now well past six, I think. I gave my electronics – Treo, Blackberry, camera – to Katie the publicist upon reaching the green room, so I’m disconnected from time. But it seems to be flowing by both quickly and interminably. Energy is ebbing and flowing now, adrenaline coming in waves. I start to worry about being summoned to the stage at an ebb moment.

They’ve left a swag bag with goodies but I growl when Fran tries to poke through it. I’ve gotten it into my head that if I resist the urge to look through it, it will somehow project a veneer of calm or cool collectedness, the path I’m carving in the carpet notwithstanding.

Fran – who along with Mom may well be more nervous than me, which is saying something – pops into the bathroom. I turn to Katie and Mom: Watch, Jon Stewart will now appear. Sure enough within about 30 seconds there’s a knock at the doorway.

I had been told so often that Jon Stewart is a diminutive man that he is taller than I had expected. (For those who don’t know me: I’m 6’5″, so I’ve heard a lot about this.) But he is otherwise no different in person than he is on any given night on television: Full of energy, full of jokes, friendly as hell. I gush that I’m a big fan, he waves it away – Oh come on! He says nice things about the book; explains that they’re running late because there’s so much tape to wade through of bloviators discussing Jeremiah Wright; waits with a twinkle in his eye for Fran to reappear; mentions that he loved a certain H.L. Mencken quote from the book; when I tell him that Fran had OK’d my writing the book on the condition that I make the Daily Show, he says: Done! Done! Kick back, have a mojito, relax! It’s done! I ask if I can bring the hypothetical mojito onstage, he waves his whole arm – come on! – bring it, he says.

I give in to my gee-whiz moment and ask if he minds a picture with me and the fam – so much for my veneer of cool collectedness.

Then he’s gone – see you on stage. A few minutes later Hilary the producer reappears and turns up the volume on the TV. We’ll watch the first couple of segments in the green room before I’m brought before the cameras and Fran and Mom are brought to a place to watch in person. I sit on the couch – finally a chance to relax.

Stewart has fun with my name – Bobby Schless! The Schless Man! – and I am doubled over laughing, grinning. This is brilliant! I am relaxing, finally. No – I can’t relax. I need my energy up. I get up and start to pace again, oblivious to whether my companions find it irritating.

The first two segments – I never do ask why they have commercial breaks in a taped show – are even by Daily Show standards hilarious. John Hodgman tells Stewart that he lacks a soul. The second segment ends – here we go. Hilary is here to take me up the stage.

I make small-talk: Is my bow-tie straight? She glances back – not quite, I’ll fix it when we reach the stage, she says. Are you going for a Tucker Carlson look? she asks. Time for some mock-outrage: Tucker Carlson? Arthur Schlesinger Jr. was wearing bow ties before Tucker Carlson was … well was something. My creativity fails me and I mutter that Carlson has given up bow ties anyway. I notice that I’m – what? strutting? – to the beat of the music blaring between segments.

We pass Hodgman in the hallway. He nods at me and thanks me for being on the show. How cool is that?! Now we’re off-stage and Hilary is fixing my tie. I ask if she can hear my heart thumping (which it is – I can feel and hear it). No, she says, adding: That’s a good sign. I watch the globe twirling over his desk and realize he’s starting to talk again.

I’ll tell you when to go on, she says; don’t look at the camera, and don’t look at the crowd; alright, go out.

It’s like skiing a challenging slope, one on which you don’t have time or opportunity to catch your breath – you start down and just react until you reach the end, hoping that practice and experience carry you through. Keep the energy up; smile; speak cleary. I get to the desk without forgetting how to walk and reward myself by grabbing for the coffee cup (full of water) like a man in the desert.

Here’s the segment.

A number of friends had asked me going in if I had a joke or two prepared; my reaction was: Are you out of your mind? I’m not going to try to force funny sitting across from someone who gets paid for it. This suspicion had been confirmed by Hilary the producer who, after a 30-minute pre-interview, had given me two tidbits: Don’t try to force funny; and we rarely know what he’s going to ask.

When Stewart asks about the Mencken quote, the comment about the quality of the speeches versus the quality of the criticism unfurls inside my head; I want to shout: I have something good to say! I have to restrain myself from cutting him off, but make sure he can’t move on. Then he asks about “flap and doodle,” and I watch as my mouth opens and words come tumbling out. I think the crowd laughed there.

Before I know it, he’s picking up the book, repeating the name again, reaching out his hand. The music plays. Now a moment of confusion: Do I leave? Does he escort me off? I’m asking how I did. See? Stewart enthuses: Piece of cake!

I suddenly remember my friends and family and turn to the crowd to see if I can spy them. “Ladies and gentlemen, Robert Schlesinger!” Stewart is saying and the crowd cheers. What the hell – I embrace the moment, spreading my arms wide and grinning like a jackanape, before grabbing the coffee cup and, with a final wave to my host I meander back into the wings.

Hilary the producer is smiling – I did well. I feel high. What do I do with the coffee cup? She tells me to set it aside. I really did OK? Yes, she says, he liked you. We’re rejoined by Mom and Fran, who are jubilant. Hodgman is sitting on some piece of furniture – a desk or bureau or something – in the hallway, apparently shooting the shit with a couple of other people. I walk up and shake his hand: I love your work. (Seriously, call me the king of trite.) He says I did a nice job.

We wander back to the green room and then out. I’m mildly delirious with happiness. I seem to have pulled it off.

For what it’s worth, nothing drove sales of “White House Ghosts” like appearing on “The Daily Show.” Over the day following the broadcast I watched the book climb Amazon’s rankings, nearly breaking into the top 100 overall.

The news last night that Stewart is stepping down filled me with a special sadness because I had always hoped for a repeat performance whenever I write my next book. Jon Stewart has become such a pop/political landmark that it’s hard to conceive of his departure. But it adds to my pride knowing that I played a bit part in that cultural landmark; it’s a large club, but its membership is about to close. Years from now when I look back upon my career, the time I nailed it on “The Daily Show” will remain a high point.


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