Insomniacs who channel surf to Fox News at 3 a.m. may think they have drifted off into a dirty, hilarious febrile dream. Instead of perky anchors and partisan shouters working over the headlines of the day, a pug-faced ne'er-do-well named Greg Gutfeld leads a motley crew of comics, C-list celebrities, and occasional reason editors through a running news-of-the-weird joke fest covering (in no particular order) free markets, unicorns, drug legalization, very attractive women, and very gay sex. Airing since February 2007, Red Eye w/Greg Gutfeld is just the latest stop in Gutfeld's checkered career.

In 1987 Gutfeld took his first journalistic job, somewhat unconventionally for a Berkeley graduate, at the conservative American Spectator, running errands for the magazine's famously erratic editor in chief, R. Emmett Tyrell. After a failed stint as a screenwriter, Gutfeld got a job at the health-oriented lifestyle magazine Prevention, where he started drinking and drugging at a prodigious rate. Gutfeld went on to edit the lads-and-abs magazines Men's Health (where he was fired for making fun of Girl Scouts, cat lovers, and his boss), Stuff (where he was fired for an incident involving several midgets for hire at a publishers' conference), and finally the British edition of Maxim, where he hung his hat while writing Lessons From the Land of Pork Scratchings: A Miserable Yank Discovers the Secret of Happiness in Britain (Simon & Schuster). Gutfeld has written "traitor" columns for women's magazines such as Cosmopolitan, Glamour, and Mademoiselle, telling women what men really think. He claims to have been rejected for a job at reason in 1988.

In 2005 Gutfeld gained a new audience by writing satirical, liberal-mocking posts at The Huffington Post (sample line: "Is Al Franken patenting the pubic hair and Elmer's glue cure for baldness, or is he just keeping the idea to himself?"). This helped lead him to his current gig, where in addition to hosting the hour-long Red Eye, he writes the Daily Gut blog. The unifying theme throughout his career has been boobs, as in both breasts and morons. Another theme to his jobs: Gutfeld was fired or forced to resign in disgrace from virtually all of them.

Associate Editor Katherine Mangu-Ward spoke with Gutfeld on stage at Reason Weekend in Orlando, Florida, in April.

reason: Describe the evolution of your political outlook.

Greg Gutfeld: As a teenager, I was a liberal. It helped me in school. Where I went to school, if you collected signatures for the nuclear freeze, you got extra credit. I realized the more you seemed to care about something, the more the teachers cared about you and your friends. If you share the liberal assumptions, you don't have to think too much about it.

I thought that was great because it really helped me with grades, but after a few debates in school where I actually had to think about things, I realized I was a complete fraud. I started to re-examine myself when I went to Berkeley. It was a really bad idea. It was just walking around with a target on your back.

I became a conservative by being around liberals and I became a libertarian by being around conservatives. You realize that there's something distinctly in common between the two groups, the left and the right; the worst part of each of them is the moralizing. On the left, you have people who want to dictate your behavior under the guise of tolerance. Unless you disagree with them. Then the tolerance goes out the window. Which kind of negates the whole idea of tolerance. That's the politically correct moralizing. Then when you become a conservative, the other kind of moralizing comes from religion. But if you remove both of those from the equation, what you're left with is libertarianism.

From the right, you've got free markets. From the left, you have free minds. To me, that's the only sensible direction. As you grow older, you kind of end up there. Especially if you drink and do a lot of drugs.

reason: Speaking of which, let's talk about your editorship of Men's Health.

Gutfeld: I was the only editor of any health magazine that did a feature on how smoking is good for you.

Actually, one of my primary interviewees was Jacob Sullum from reason. He turned me on to all these tobacco companies that were actually doing amazing research on Alzheimer's and Parkinson's. But nobody in the media would cover it because smoking is bad. I would get all these amazing medical journals at Men's Health, and I loved them mainly for the weird pictures that I would copy and send out to my friends, enlarged arms and weird faces. I believe I was the original Internet.

I read a lot of this passive-smoking stuff, and I realized it was just bullshit. What they're trying to do is create science to legislate. I wanted to write about this, and I'd just become editor of Men's Health. When you get a job like that, you're supposed to do the right thing. I did the wrong thing.

The article I wrote was called "I Smoke and I Work at Men's Health." We recreated a Parliament ad with me in the middle smoking. It was really cool and wonderful. I interviewed every satanic person in the tobacco industry and cited their science. It was a fantastic article, and it dropped like a stone in journalism. People just hated it. But I couldn't help it, because this is real health journalism. Once they stop demonizing substances, they're going to find out that these things can actually help people.

Health editors are generally very miserable people. They constantly think there's something wrong with themselves. Meanwhile, they hate pharmaceutical companies.

Here are companies that have to bend over backwards to tell you what's wrong with their product. Those commercials, 90 percent of the commercials are them telling you not to buy it. Meanwhile, health editors are lying to you. They're telling you that New Age practices work. So you have these people that are making fun of drug companies who are liars, and the drugs companies that can't afford to lie. I realized that the pharmaceutical companies to me were bigger than the space program. They spend billions of dollars on tiny little things that change your life, and no one gives them credit for it.

Men's Health is where I started to get very pro-business. Like, you know what? Corporations are not these evil monoliths that they depicted in Michael Clayton. They're just groups of people who work really hard to create good things that make our lives better, and they're treated like crap by editors who are paranoid weirdos.

reason: When I was on Red Eye, we talked about some findings about marijuana and life extension. It's not just the big pharma drugs that can help people, right?

Gutfeld: Yeah. And I won't just say marijuana. I'll say Ecstasy, acid, cocaine. People take these things for the sake of oblivion, but they also work. If you treat them like any other substance, you can actually derive what makes them work and turn them into things that help you. Pot helps people who are in pain. There are studies that show that Ecstasy helps heal problem marriages.

reason: At Stuff, in your words, you turned this "dumb news magazine into the most hedonistic, moralistic, hippie-hating magazine on the planet. It was relentlessly pro-America, pro-business, and antielitist."

Gutfeld: All these magazines are done by editors who talk to other editors—Esquire, Details, GQ. They're actually not read by anybody. Most of these magazines are bought up by agencies and dumped so they can charge higher ad rates. However, guys read Maxim and they read Stuff, because in there are things that actually relate to their lives. I looked at Stuff, and I thought it should always be about the unspeakable truths, the things that you know are right in your gut, that everybody else says is wrong. Magazines like Esquire, the truths in there are made to appeal to other editors, to make them feel good when they're at lunch. So they'll do a story shitting on the military because they know that that'll make the other editor feel good.

Meanwhile, at Stuff, we decided we're going to do a survey of the military. I just sent people out to installations and asked them questions about life, and it was an amazing thing. I also did that with death row inmates, which was equally interesting and somewhat more disturbing because they sent pictures. Death row inmates love to draw, and they love to write poetry.

reason: What was better, the death row art or the medical pictures?

Gutfeld: Well, the medical pictures are great because there's an endless supply of what you can do with the human body.

reason: You put up one of the very first posts at The Huffington Post, which turned out to be a massive liberal blog empire. When it first started out, it was not as clear what it was going to be, but by the time you left all the other contributors and most of the readers hated you. How did that happen?

Gutfeld: I decided I was going to treat The Huffington Post like a message board for criminally insane shut-ins and start posting things like recipes. "I found a sex toy on my lawn. Will someone claim it?" And then I would use the names of the people on the blog: "David Gergen, you left your cycling shorts in my basement." I would just treat it like that so that when the real politics came up, it made no sense. There'd be this serious piece that would come up followed by an invitation to a strange party in my basement—everybody bring Crisco!

It was a lot of fun because it created so much hate and vitriol. It ended up revealing that the most tolerant people in the world are the least tolerant. These are the people that pride themselves on being open-minded, but they're only open-minded if you agree with them. I just kept poking them and poking them like a stick on road kill until finally I got bored. And also they got tired of me and started moving my posts away into the back, and then Fox News called me and I ended up at Red Eye.

reason: A lot of people who watch your show have noticed that, in between the unicorns and the Crisco, there's actually some serious policy wonkery.

Gutfeld: Sometimes the unicorns and the Crisco come together.

There are three things that I could go off on forever. Global warming is the biggest scam ever devised. It's created by media-savvy folks who saw that they could get on TV much easier if they create concern. They purposely ignore scientists who don't follow the party line, so I do that story a lot. Everybody hates it because even though they agree with it, it's boring, but the most boring things are the things that kill you.

The second issue is the way the media portray people that they disagree with. They were far behind the tea party story. They didn't know how to catch up, so rather than try to catch up, they made a joke out of it: "They're a bunch of tea baggers." It's a really funny joke. It's like they kept saying it over and over again, but it was stupid and it was demeaning. I'm not a joiner. I didn't go to the tea parties, but everybody I knew that went to the tea parties had jobs. They owned things. They're not going to throw a chair through a window because they probably owned that store or they owned that chair.

The third thing is the drug war, which is a waste of human life and a waste of money. We've been through this with Prohibition. I don't know why we can't see that this thing is just killing our country. No pothead should be in jail.

They're the nicest people on the planet. The worst thing they do is they eat all your food. That's not against the law. Cokeheads, they talk your ear off. They tell you stories that you don't want to hear. The next day they regret it, but that's not a crime. Meth heads will take apart your toaster, try to put it back together. It never works, but you hide the toaster. That's all you do. You don't put the guy in jail!

What we're doing is we're putting people in jail who are following a natural human need, which is just to get out of life for a few minutes or for a few hours. I don't think it'll ever change because no politician that will be elected will ever have the balls to actually do something about it.

reason: Journalists are always on the lookout for trends of three, and we may have one with people who suddenly want to use the word libertarian to describe themselves on television. You've got HBO's Bill Maher, you've got Glenn Beck on Fox, and then there's you. Should we make anything of this?

Gutfeld: Bill Maher is not a libertarian. He's not even close. He's a P.C. liberal. The fact that he called his show Politically Incorrect is an absolute lie. If you watch Real Time and watch what he does to those that don't tow the left-wing line, it's a crime. He'll have a Professor [Michael Eric] Dyson on to talk for hours on this postmodern crap, and then he'll go to Andrew Breitbart [creator of Brietbart.com and former editor of The Drudge Report]. Then when Andrew Breitbart starts talking, he'll make a joke and everybody will laugh. His trained seal audience of retarded nutbags will clap. And then the segment will end. So it looks like you saw two voices, but you really didn't. You heard this very long diatribe. I hate that guy.

Libertarianism is a very cool thing to use as a disguise. Bill Maher does not say he's a liberal. He says he's a libertarian. That's the reason why he does it. I think Glenn Beck is a libertarian, but he's also got a very strong religious component, and it's hard to put those two things together, I guess. But I think that "libertarian" provides cover for a lot of people.

Bonus Video: Watch Greg Gutfeld and Reason's Katherine Mangu-Ward discuss media bias, liberal intolerance, and why drugs really, really, really need to be legal.