Conan O’Brien’s Love/Hate Relationship with the Internet

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Back in January Conan O’Brien was supposed to come to San Francisco for a SF Sketchfest Tribute and Q&A about his career. And then, he lost his dream job as he said, “shit really hit the fan” and he had to cancel. He finally made good on that gig last night at the Herbst Theatre in San Francisco, and it was far more revealing than his 60 Minutes interview. I’d gone expecting to hear an “Inside the Actor’s Studio” style retrospective. What we got instead was more than three hours of O’Brian, Patton Oswalt and Andy Richter drinking heavily on stage and talking about how the Internet has utterly ripped the media business in two over the course of their careers.

“Those men behind the curtain—the great and powerful Oz—are scared shitless right now,” O’Brien said, adding that the chaos is so high that anyone in the audience could just as likely be running a major network in a few years. O’Brien opened by saying he was choosing to see opportunity in the volatility in his business, but over the next few hours it was clear that it wasn’t that simple.

What O’Brien went through with NBC was a more public version of hundreds of conversations I’ve had over the last ten years with people in old-media, music, independent book stores, and travel agencies—especially people who are mid-career and young enough to want to disrupt things, but old enough and have paid enough dues that it somehow feels unfair when the industry is ripped out from under their feet. To me, this three-hour out-pouring of enthusiasm for the future mixed with nostalgia of the past was like any conversation I used to have when I still worked in old media newsrooms. I wish he’d been this frank in his network interview—because this is the everyman story of the Web’s disruption. If it hasn’t happened to your industry yet—wait. It will.

If I could just embed a raw bootleg video, I’d end this post here. But given the theme of the evening, it was sad but somehow not surprising that SF Sketchfest emphasized several times that no video or photos were allowed—a contrast to O’Brien’s comedy tour when he welcomed fans to record and do whatever they wanted with the footage. That means these raw, authentic confessions and advice to the younger creative generation can’t run on the platforms where audiences would most appreciate them.

So here are my highlights instead. (I wasn’t taking notes, so I’m paraphrasing here.)

Just How Much Has Changed: O’Brien talked about when he got the Late Night Show job in 1993. He was so unknown that no one could find a photo of him to run with the news story. Imagine: No TwitPic, no Facebook profile image, no Flickr—nothing. Newspapers ran a gritty image they snapped from the television screen instead. And it took him several days to get a photo together to send out.

Today, anyone with his level of experience at the time would have thousands of clips from YouTube, from tried-and-failed cable shows, live video from standup gigs, maybe an appearance from a Funny or Die skit, not to mention thousands of images online. On the one hand, he said it had opened up opportunity for funny people everywhere, especially women, African Americans and other minorities that don’t get as many plum jobs in the entertainment world. But on the other hand, if he were up for that job today, he admits there’s so much competition he probably wouldn’t have been given a shot.

Cream Rises…or Does It? O’Brien made the point repeatedly that “cream rises to the top” online and that if you consistently put out funny stuff, you’ll start getting paid to write or perform funny stuff. But he also talked about how the Web and the reality TV/ Paris Hilton generation had set a precedent that you could be famous not for any talent, but just for making a spectacle of yourself.

He cut himself off talking about the latter, saying he was trying hard not to be judgmental—but this is clearly an idea with which he struggles. He talked about kids coming up to him and saying they were going to be on his show one day and when he asked what they did they said “nothing,” but they were “going to be huge.” He said a few decades ago if someone had said that to David Letterman or Johnny Carson the answer would have been that they sing, dance, act or something.

Success Was Being Left Alone. When O’Brien first took over Late Night the network wanted to put him on a week-to-week contract. He fought back and got a series of 13-week contracts. He and his staff did their job with the feeling that the anvil could fall at any moment. But because no one had much hope pinned on the show, they were largely ignored and allowed to do whatever they wanted. They’d throw stuff out there, and if it worked it did, if not, they’d throw more stuff out the next day. The contrast to his practically non-existent honeymoon period on the Tonight Show is obvious.

Here’s the good thing about a Web-distributed entertainment world—there’s a lot more of the former because the gate keepers are disrupted. It’s no longer an age where there are only three networks. If you want to entertain people and do good work, there a million steps in between all and nothing.

Developing a Thick Skin Is Bullshit. O’Brien said the biggest thing that held him back from both writing and performing was a fear of being criticized because he’s incredibly sensitive. He punched a big hole in one of the biggest clichés in fame—that you just have to develop a thick skin. He says he’s still just as sensitive and criticism still hurts just as much. The secret is to just keep going anyway, because you will get criticized no matter how brilliant you are.

This is clearly something that’s gotten more pronounced in a Web age, but there may be a silver lining to that. In a time when every video, photo, blog post and Tweet can easily be trashed by others, people learn that criticism is inevitable early on.

Longevity Is the Most Overrated Thing on TV. O’Brien talked about how people on TV measure success in how many years their show runs, and that he thinks that’s the wrong metric. It’s not about how many people watch you for how long, it’s about the connection you have with those people, he said. To anyone in the room, this was clearly heartfelt. I’ve heard O’Brien in interviews before the Tonight Show debacle, and he always seemed glib and jokey—almost to the point of insincere. But last night—and I’ve heard during his comedy tour—he was raw, clearly shaken by what happened with NBC and clearly touched by the outpouring of support he got from fans, enabled largely by social media.

He said several times how much people loving his work enough to support him – even if that support was a mere two-second Tweet for “Team Coco”—meant to him and how it kept him going. He clearly didn’t want to leave the stage. He threw the clock off the table when he sat down asking why there was a time limit, and towards the end sat on the edge of the stage taking questions from the audience long after they’d said they would take “just one more question.”

The evening was billed as a tribute to O’Brien, but he turned it into a tribute to his fans connected around the world by social media instead.

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