Monty Sarhan, the corporate lawyer-turned Editor-in-Chief of the humor mag Cracked, on brilliantly written court decisions, Michael Ian Black, the over-ratedness of the Big Lebowski, and how he made The Funniest Magazine in History funny again. Interview by Brendan Ballou.

How late were you working last night?

Last night, I think until about 7:30. The major thing about doing something entrepreneurial is that you never really stop. I mean, I go home I check my email and I’m still doing stuff. It’s really hard to unplug, it’s like having a baby.

Have you had a baby?

No, I haven’t. I imagine this is what it’s like.

I’m really excited. We had Ben Stein last month, then Dan Okrent from the Times, and we’ve got you.

You’re going downhill. You start with Ben Stein and now it’s going downhill.

What I want to know is – how do you write a joke?

Well, there’s lots of work. First and foremost it’s a business. We’re in the business of creating content and entertaining people – every single day on the website and every two months in the print magazine. It’s more that we think about what’s everybody talking about, the topics that need to be made fun of, who needs to be brought down a notch, what’s wrong with society, what’s going on in politics.And then we start to have this free-form discussion in editorial meetings where we just start going off on opinions and stuff and the jokes start to emerge from that. You start to make fun of the ridiculousness of, you know, Mel Gibson getting stopped, or Tom Cruise, or what’s going on in the war. And obviously you can’t make a joke about people dying in the war, but you can make a joke about the ridiculous political atmosphere that surrounds the war here. So the jokes kind of occur naturally.

Who are most comedy writers?

They’re mostly introverts with bad hygiene. No – I think it’s anybody who’s observational in nature and has a skewed or different perspective on the world. They have some sense of detachment so they can look at things and be able to comment on them. I think those are the comedians we try to reach out for.

You used to be a lawyer – how is this job different?

It’s a lot more fun. Being a corporate lawyer is about putting deals together. Somebody’s buying a business, someone’s selling a business, someone’s raising money, so in the end of the day people are happy. I didn’t do stuff like bankrtuptcy or stuff like that so corporate law for me was fun. It teaches you how to think analytically and take stuff apart. This job is a lot more rewarding than being a lawyer because ultimately you feel good about yourself. I mean, you feel good when people pick up your magazine, they read it, they laugh about it, they write to you and say it’s hilarious. We still get excited every day we get a massive traffic day on the website. I mean we have 75,000 people on our website right now. That gives me a rush. We’re not even that big – we’re not yahoo or something – but for us 75,000 people are reading our stuff right now – that’s great.

How did you become a lawyer?

I went to law school.

But was this something where you became a lawyer, but your whole life you were dreaming of being a comedy writer?

I always wanted to be a writer, I always wanted to work in entertainment. You figure out what you  want to do in life and there are different paths so you can get there. I was very curious about the business world [but] I didn’t want to get an MBA. I liked the rigorous nature of the law degree, still a lot of reading and writing. Some of the best literature in the United States are court opinions. You read an opinion by Learned Hand, and there’s such great language and dicta in there. To me that was part of becoming a writer and shaping who I was.

Who do you like in comedy?

I think Michael Ian Black is underrated – he’s one of our editors at large. He’s on VH1, I love the series. He has a new movie coming out. He’s a very, very, smart, clever writer, and a talented comedian. I think Dane Cook is overrated right now. I think Charlie Murphy is very talented. Dave Chappele – hugely talented.

Obviously there’s a whole show behind them and a staff of writers but I think Colbert is great. Jon Stewart, very clever too. But it’s the staff of writers – a lot of people don’t give props to the writers. They don’t realize what goes into putting a show like that together, or putting a magazine together, but it’s a team effort. One guy gets the glory.

The Onion is great. We do something completely different from them so I don’t mind giving them  the respect that they deserve. The Onion is very funny. They’ve perfected what they do, but they only do one thing, and that’s fake news. They don’t do anything else beyond that. They take a headline and they rip it, and most of the time they make it fictitious. We try to have all of our writing based in reality. We make fun of politics and culture too, but the Onion makes it fictional, and we try to keep it real and actual news.

After a while at this job, do things stop being funny?

By the time we put an issue in the can and it goes to press we have all read each one of those pieces 10, 15 times, and we can’t tell if it’s funny or not. And so you have to think back and ask, ‘well, did I laugh the first time I read this?’ Because after a while you just can’t tell anymore.

Did you read Cracked as a kid?

Yeah. Mad and Cracked, and National Lampoon, and Spy. So there’s a little bit of all those magazines in this.

Were those your formative influences?

Yeah, pretty much. This was what was around for entertainment. This was before the 500 channel cable universe. I wasn’t really a comic book fan, so I was really into the [magazines] for the comedy.

Do you think it’s a loss to have so many sources of comedy – that we don’t all have some shared humor?

No, I think it’s always better. I think the more voices that get heard, and the more stuff that gets out there the better. It certainly makes our job harder, because once you put together a magazine – you’re making fun of events that everyone has commented on and blogged on anybody who has a copy of photoshop already doctored a photo. Everything’s been done, you really have to take it to the next level and be so outrageous. It’s good, it forces us to be competitive and really bring our A game to the thing.

You tried to buy RKO Picture’s unused scripts. How did you find out about this?

I was a media lawyer, and I was doing a lot of TV and film deals. And RKO pictures, for anybody who’s a film buff, knows about RKO pictures. You just have to pop in an old movie and you see that globe and that radio tower beeping. And that logo is so iconic. I grew up watching film and just loved it and just ate it up – Citizen Cane  is probablty one of my all-time favorite pictures. Fantastic – the guy’s a genius

Yeah, about your favorite movies – what’s with all these movie posters on your wall.

They tend to just be comedy movies that I liked. And then there’s some superhero stuff that I liked. But they’re mostly like what I’d say are the best comedy movies of the last decade. I’ve got to say though, I think the Big Lebowski is overrated.

Really? But it wasn’t at the time. It was a cult film that had an underground following. I liked it when it first came out, so I thought it was underrated at the time.

I just now feel like it’s disproportionately loved. Yeah, now they have festivals and people who are obsessed with it

And who only drink white Russians. But I got us off track – RKO pictures

Oh yeah, so a friend of mine who’s a producer in LA mentioned, ‘hey, I think there might be people out there who would be willing to sell.’ For me that was a huge trip. They had already sold the film library to Ted Turner in the 80’s. but what they had were the archives of unproduced screenplays and they also had the remake and sequal rights to most of their library. So it was valuable from an intellectual property perspective. And so I worked on that for about a year

But it didn’t work out?

You know, deals fall apart for lots of reasons. The editors at the end of the day had mixed thoughts about whether they wanted to sell or not, and at the end they decided not to sell. But that’s okay because if I had been  working on that I probably wouldn’t have found out about Cracked and here I am.

So how did you find out about Cracked?

Again, I was raising money for RKO, and a friend of mine called and said, ‘hey, you’re trying to do this RKO deal, and if you build on RKO it’s really about taking this famous brand that people have a really strong relationship with and recognizes, and giving back in a new in different way.’ He said ‘Cracked is available too if you’re interested. It’s also a very iconic brand, it’s been there for 50 years.’ He was just thinking about it for what it was ‘you know, the artwork’s worse but you could really get some good artists and bring it back to New York.’

50 years ago when Mad and Cracked first started that was the only way you had to  parody things – hand drawn illustrations. There was no photoshop, there was not animation. That’s the only thing we had. I think it’s a little anachronistic to still be doing that stuff today, and I didn’t think that a magazine that only did that could survive. So I said, ‘No, I’m too busy, I’m not interested.’

But then I started thinking about what it meant to me to read it as a child and all the stuff that I used to enjoy reading wasn’t even out there. Mad and Cracked had both lost relevance, both lost huge audience share. There was no National Lampoon today, there was no adult humor magazine.People today don’t have that stuff. Yes there’s the Daily Show, and you can make the argument that yes we don’t have that stuff on newsstands because we get it from other places:  we get it from the Internet, we get it from blogs,  we get it from cable television. But as a magazine, you’re not going to do the same kind of coverage of anything the way that the Internet does it or the way that television does it. We have to therefore have to be more thoughtful, more deliberate. We have to talk about trends rather than just focus on little incidents.

So your friend calls you up – what happens next

I say I’m not interested. And probably a couple of months went by and I kept thinking about Cracked, and it was just there in the back of my head, and I was just perplexed by it. I thought there has to be some value in there to be unlocked. It’s not funny anymore, the artwork’s not good, the sales are down – and by the way you can say the same thing about Mad. 

I stopped thinking of Cracked as a comics magazine, I stopped thinking of it as a kids’ magazine. I started thinking about it as all the things it represented in my childhood, all the things that were no longer there in the marketplace, but there was still a need for. It’s not like people stopped reading. It’s not that they’re not hungry for humor. They are hungry for humor – The New York Times launched a humor section for the first time in its history. People go out and buy the Daily Show’s America: the Book. It’s not like people turn on the TV and zone out. There’s still that kind of need for comedy plus commentary. So I started thinking of Cracked as just a brand. Here’s a brand that’s been around for 48 years that just about anybody ove the age of 15 has seen, or picked up a copy of, or seen in the bookstore, or knows someone who has read a copy, whatever. If you think about the kind of investment that was made in that brand over the course of 50 years, you’re talking about a brand that’s worth literally millions of dollars. So how do you take that untapped asset and reinvent it and make it useful? And so it was sort of a mental exercise – what can I do with it?

The fact of the matter is that if I had started a new magazine called Funny or Jokes nobody would have written about me – the New York Times wouldn’t have written about me. They wrote about because it’s Cracked. Somebody’s taking back Cracked.

Check out Monty’s MySpace!