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Creative terror and cat names: The story behind the launch of our site

On the day Jimmy Kimmel’s late-night show was launching in Hollywood, he woke up in San Diego, about 100 miles away. Jimmy was producing a Super Bowl show there for MTV,1 so we drove down on that weekend in January 2003 in a party bus normally reserved for wild bachelor parties. You could practically smell the stale champagne and DNA on the seat cushions. I remember cars honking at us as they passed, assuming something crazy was happening behind the tinted windows. Nope. Unless you count Jimmy’s cousin Sal waiting for people to fall asleep, then farting on their heads.

Only Jimmy’s inner circle was invited: his girlfriend, Sal, two executive producers and two buddies, along with two other writers and me. We spent two straight days eating, drinking, cracking wise and attending Super Bowl parties, with the shadow of the show’s premiere hanging over everything. Jimmy seemed especially calm, his confidence buoyed by recent successes with The Man Show and Crank Yankers. Because of that, nobody else seemed overly concerned, overwhelmed or however else launching a heavily promoted show on live television should make you feel. Me? I was a nervous wreck. I wanted to throw up. But I wasn’t going to tell anyone else that.

We left San Diego four hours before the game kicked off, heading back for that night’s live telecast. Going live was one of the brainstorms that, hopefully, would differentiate us from the other shows. We wanted a festive atmosphere, so we treated our audience to an open bar before every show. We wanted a different guest host every week, a celebrity foil who would hopefully lend unpredictability to every show (a little like the old Mike Douglas shows, when two or three guests would be yammering at all times).2 We wanted Jimmy starting every show behind his desk, without a tie, delivering off-the-cuff remarks instead of a traditional monologue (for the first few shows, he didn’t even have a script). Different. That’s what we wanted. Jimmy was younger than every other late-night host at the time. We wanted his show to feel that way.

We thought we were reinventing the late-night format, actually. The test shows said otherwise — one was bad, one was a train wreck, two were fine — but when you’re that close, you ignore red flags and concentrate on the positives. You have no other choice. Halfway through the ride back to Hollywood, we stopped at a Carl’s Jr. to scarf down lunch and use the restrooms.3 Jimmy and I found ourselves waiting outside the restaurant afterward, with the sun shining and the tension mounting. I found it really hard to believe he wasn’t freaking out.

“How you feeling?” I asked.

At that specific point in time, every member of his staff was chugging the Jimmy Kool-Aid. That’s the only way these things can work. Dozens of people had placed their careers in his hands, including me: I had (effectively) given up my ESPN column, left Boston, left my family and dragged my fiancée to Los Angeles, simply because I had grown up idolizing Letterman’s NBC show — like Jimmy, actually — and always wanted to write for something similarly inventive. Jimmy and I spent the summer of 2002 talking on the phone and trading e-mails, and at some point, I made the decision, “I believe in this guy.” So on the biggest professional day of his life, with that shadow hanging over both of us, I needed a really good answer for the question, “How you feeling?”

Eight and a half years have passed. I can’t remember how Jimmy answered, just what his face looked like. You wouldn’t call it nervous, you wouldn’t call it overwhelmed, you wouldn’t call it anything … he didn’t fucking know.

Life will deliver a few moments when something substantial is about to happen, when you know it’s substantial, when you’ve done everything you could to prepare for the moment, but still, you just don’t know. And it would be foolish to pretend otherwise. I felt that way when I was getting married, when both of my kids were being born, when I graduated college,4 and incredibly, when I was standing in front of that stupid Carl’s Jr. Oh my God. There is no stopping this now. Please tell me this will turn out all right. You take a leap of faith with life. You inhale and exhale. You hope.

We made it back to Hollywood an hour later, with Jimmy becoming more and more quiet during the ride. They had shut down Hollywood Boulevard so Coldplay could play on the street, right between our stage and the famous Mann Theatre. As we neared the congestion, it was like someone tossed 500 pounds of tension into the bus. Holy shit, that’s for us? I ended up in Jimmy’s office with Sal, who had quickly become my closest friend on the show. We were assigned to watch the Super Bowl, jot down possible jokes and find possible cuts for clips. (I know, some job.) The office hugged Hollywood Boulevard, with Coldplay’s crew working on their stage almost directly underneath us.

At the time, Coldplay was threatening to become the biggest band in the world. Even if our guest list for that first show included George Clooney, Snoop Dogg and the Super Bowl MVP flying in by helicopter, shutting down Hollywood Boulevard for Coldplay would be that night’s haymaker. No late-night show had ever done anything like that. We were catching them at the perfect moment of their career: right after their second album had flown off the shelves, right as people were wondering if they were the next U2, right before Chris Martin started boasting a little too much and the inevitable backlash kicked in.5

The fifth song on that album is “Clocks,” the one that starts with those pounding piano chords (the defining hook of any song they’ve written). Sal and I were engrossed in the Raiders-Bucs game when suddenly “Clocks” started cranking six floors below us. It was Coldplay. Rehearsing. Really, really loudly. The song went for about a minute (no vocals), then it stopped. There was a long pause. Then the pounding piano chords started again. It went like that for about 25 minutes: the world’s hottest band rehearsing its music, the Super Bowl winding to a close, our lives just a few hours away from being changed, that shadow looming … and nobody knowing what would happen next.

Every time I hear “Clocks,” I think of staring out that window and wondering how I got there. That’s still my most vivid memory from a frenzied first night. Even before we started the show, a drunk girl in the audience threw up right in front of two Disney suits. (So much for the open bar; by Monday, it was gone. Although it did end up being funny fodder for the first show.) Jimmy’s monologue ended up being too loose; compared to other shows, it felt like he had wandered into the building and just starting winging it. We somehow gave Clooney four minutes and Warren Sapp two segments, which made no sense even as it was happening. At the same time, there was something refreshing about how we discarded the traditional late-night format and did our own thing, sloppy producing and bad luck aside. Coldplay’s two songs stood out more than anything, not just the music, but the sheer spectacle of it all. When Jimmy screamed, “Ladies and gentlemen, Coldplay!” to a throng of people, he could barely contain his joy. This was everything he ever wanted.

We were all delighted by that first show; you can’t maintain any semblance of objectivity when you’re that close. We packed into a deliriously happy greenroom afterward, a place that became our legacy for the first year within Hollywood circles — maybe the show wasn’t catching on, but it was a helluva place to hang out. Somebody had made a party mix CD that played the same sequence of songs after every show,6 with the first one being “Beautiful” by Snoop Dogg, one of the happier hip-hop efforts of that era. The right combination of beautiful girls, sleazy agents, hangers-on, executives and C-list celebrities were in place — like an Entourage scene before we even knew what Entourage was7 — and within a few days, once we started worrying about the show’s future, I always looked forward to hearing “Beautiful” because it brought me back to that night when free drinks were flying and we weren’t worried about anything.8 Some people crammed into Jimmy’s office; others crammed into Snoop’s dressing room; everyone else imbibed, mingled, and waited for an invite to one room or the other. We had successfully launched a late-night talk show without going down in flames. Everything would be fine.

Or so we thought.

Over the next 12 months, we realized that we needed to discard some of our edgier ideas; not because we didn’t like them, but because there was a reason nobody else was doing them. People like continuity with late-night shows. They don’t want to see new ground broken. They don’t want reckless chances and unpredictability. They want to see a friendly-looking guy stroll out wearing a suit and tie, stand in front of the camera, tell some jokes, throw it to commercial, sit behind a desk, and talk to guests. They want this because they’re lying in bed, half-asleep, with their brain slowly shutting off. And so our big ideas started disappearing one by one: the live taping, the guest co-host, the untraditional monologue, the guest announcers, Jimmy starting the show behind the desk, Jimmy not wearing a tie … as if a network sniper was painstakingly picking them off.

Jimmy adjusted on the fly because he’s talented and that’s what talented people do. Act One slowly developed an identity, built around funny clips found on various shows.9 We figured out a creative structure for the day and weeded out every shaky hire. Jimmy realized he couldn’t be so abrasive with guests; only a few PR people control most of the real celebrities and D-list celebrities, so when you tick them off, they freeze you out.10 He realized it didn’t make sense to take potshots at Jay Leno and play the “up-and-coming guy taking a shot at the established guy who can’t fight back” card, because, actually, Leno could fight back: His staff told every PR person that if they did Jimmy’s show, they weren’t allowed on Leno’s show (which had a much higher rating). He even realized that Act One required him to deliver a standing monologue while wearing a tie. It took Jimmy four or five years to reach his potential as a host, then another two before anyone noticed. Now he’s entrenched. Unlike just about everyone else, his ratings are climbing instead of dropping; he just enjoyed his highest May Sweeps ever. As Jimmy says now, “the show evolved as naturally as a network TV show possibly can — it was a trial by fire.” And it was.

I spent the first 18 months working for Jimmy and the next seven years rooting for him. In April of 2004, I left his show and returned to ESPN — a move that had been brewing for 11 months, ever since we filmed a feature with Mike Tyson on an decrepit rooftop in Harlem. The plan was for Tyson to show off his pigeon collection for Jimmy’s Uncle Frank, a retired policeman and recurring character on our show. As a die-hard Tyson fan, it was shocking to see him this way: his career in shambles, his inner circle dwindling to just a select few, his formerly lavish lifestyle long gone. He spent his days getting high on medical marijuana (harder to get back then) and being generally strange. For whatever reason, he wanted to co-host our show for a week. Now he was showing Frank how to fly pigeons, only Frank was (and is) such a sweet man that it disarmed Tyson and unleashed a softer side.

We expected the piece to be funny; this was something else. A moment, if you will. And I was processing it as a writer instead of a TV writer. I didn’t want to be there with cameras, I wanted to be there with my notebook. That’s when I knew I had to leave, only I loved working for the show enough that it took another 11 months before I did. Jimmy and I remained friends; my wife and I remained in Los Angeles. Jimmy teases me that I left because I wanted to watch more TV. Deep down, he gets it. People should do what they’re meant to do. I was meant to write columns. Over the past seven years, that’s what I did. But there was always something nagging inside me …

… this little thing that I had always wanted to do …

… this website that wouldn’t stop forming in my head …

Fast-forward to 2011: On Friday night, we were hanging out at the Hotel Figueroa, which has a sneaky little pool bar about two blocks from our Grantland offices.11 One of my coworkers asked if I was getting nervous. I think I said no. What did my face say? I couldn’t tell you. Everything comes around, I guess.

I would love to tell you that this website will work, that we’ll entertain you five days a week and blend sports and pop culture successfully. The truth is, I don’t know for sure. This site will keep changing over the next few months just like Jimmy’s show kept changing in 2003, hopefully for the right reasons and not the wrong ones. We are still hiring people. We are still finding writers. We will eventually have a sports blog and a pop culture blog (launching next month), user comments (later this summer), a podcast network (ditto), a quarterly publication we’re doing with McSweeney’s (four a year, starting this winter), and who knows what else. You figure out what works, you figure out what doesn’t work, you keep moving. That’s the next nine months for us. Eventually, we will evolve into what we are. Whatever the hell that is.

We had four goals for this site. The first was to find writers we liked and let them do their thing. The second was to find sponsors we liked and integrate them within the site — so readers didn’t have to pay for content, and also, so we didn’t have to gravitate toward quantity over quality just to chase page views. The third was to take advantage of a little extra creative leeway for the right reasons and not the wrong ones.12 And the fourth was to hire the right blend of people — mostly young, mostly up-and-comers, all good people with good ideas who aren’t afraid to share them.

In the months leading up to this launch, which became something of an administrative abyss for me, my favorite times were always taking the staff out to get food, then brainstorming ideas and making fun of each other. Those are the memories you end up taking with you, the little stuff, like the time I logged into my e-mail during a staff meeting, the AOL guy screamed “You’ve got mail!” and everyone broke up laughing as if I had been shot out of a time machine. Or a month of comedy mileage (and counting) that we’ve gotten from one of our writers confessing that he wanted a cat. We have made 10,256 jokes about this cat. We’ve named it 247 times. I will always remember this stupid cat that doesn’t exist.

We haven’t had a Coldplay/Hollywood Boulevard-type moment yet, and honestly, I’m not holding my breath. But our staff has bonded much like Jimmy’s staff bonded eight years ago, and regardless of how this plays out, nobody can take that away. Writing is a fundamentally lonely thing. It’s just you and a blank Microsoft Word document. The process can drive people crazy. (And has.) It’s much more fun to create something with other people. It just is.

I have done it twice before: with Kimmel’s show and “30 for 30.” This is the third. With every launch, there comes a point when you grab everyone else’s hand, you hold on tight, and you jump. You’re never really ready. That’s what Jimmy’s face was saying in front of that Carl’s Jr., and that’s what my face is saying now. Even if you can’t see it.

Enjoy the site. We worked hard on it. We believe in it. And that’s all I know.

Bill Simmons is the Editor in Chief of Grantland and the author of the recent New York Times No. 1 best-seller The Book of Basketball, now out in paperback with new material and a revised Hall of Fame Pyramid. For every Simmons column and podcast, log on to Grantland. Follow him on Twitter at http://twitter.com/sportsguy33 and check out his new home on Facebook at http://www.facebook.com/billsimmons.

Filed Under: Bill Simmons, Grantland, People, Simmons

Bill Simmons is the founding editor of Grantland and the author of the New York Times no. 1 best seller The Book of Basketball. For every Simmons column and podcast, click here.

Archive @ BillSimmons