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Funny Business

With a career in the format stretching over 25 years, the elder statesman of the modern late night talk show is inarguably Conan O’Brien.

Following stints at Saturday Night Live and The Simpsons, O’Brien took over as host of NBC’s Late Night from David Letterman, who had himself moved to CBS to host The Late Show.

The media was quite critical of O’Brien’s first year, especially considering who he had replaced.

However, Robert Smigel, the head writer of Late Night in 1993, wanted to emphasize that this new incarnation of the program came with different sensibilities:

“I set down a lot of rules, some of which were crazy, but ultimately it forced us to come up with a lot of original stuff. We had the added bonus of being Letterman’s replacement.”

Decades passed.

O’Brien became a beloved icon of late night, a household name.

Controversy surrounding his replacement of Jay Leno on The Tonight Show in 2009 ended up securing him an eponymous show on a new network.

To promote a reboot of that program, O’Brien recently spoke to The New York Times, reflecting on his early days:

“We’re trying to be anarchists, but I’m trying to be a good boy and do a good job for the network.”

This seems like a perfect encapsulation of some of the difficulty that modern advertising faces.

The simple act of living is inherently risky, and yet we’re afraid to take risks with our work.

Perhaps this can be waved away as consideration - we don’t want to upset anyone, and we certainly don’t want to give our bosses any reason to fire us.

It’s not as though I’m unsympathetic to these viewpoints.

But what, exactly, has being good boys and girls gotten us?

Maybe the most boring and ineffective procession of advertising in memory.

Digital media, where the vast majority of advertising spend goes, is safe, and in some cases arguably even effective.

Any marketing department will end up doing a lot of extraneous things, on multiple platforms, not because there is anything worthwhile to say, but because of the expectation that they should be done.

But when was the last time you so much as heard a conversation with the sentence, “I saw this great ad online”?

O’Brien decided to retool his show to make it closer to what he wants it to be.

The desk, eternal staple of talk show sets, is gone.

He’s traded his suit jacket for a leather one.

There are a bunch of new avenues, like a podcast and a stand-up tour, for him to explore creatively.

Everyone in this industry can take a lesson from his experiences.

We’re meant to be anarchists, to make trouble, to get people who don’t care about who we are or what we do talking about our client.

But whether it’s because we’re happy to have a job or we just don’t want to think, we’re content to fall in line.

I wonder if he’d find that funny.

Matt