Dave Barry has been a small L libertarian since early in his journalism career. This is from the Advocates For Self Government site:
No, we are not making this up! Humorist Dave Barry is a libertarian, and has been for years. In a 1994 interview with Reason magazine, Barry credited writer Sheldon Richman with convincing him to embrace libertarianism, back in the 1970s.
"Sheldon and I would argue," Barry told Reason. "I mean, really argue.... Then in the late '70s, I begin to see. I think the gas crisis had something to do with it. I began to realize, this is all happening because of the government. And I began to think about all the government people I knew ... who were theoretically for the common good. Then I realized not one of them was [for the common good]." That led Barry to his ultimate insight about government: "It's stupid."
Barry was even more explicit about his political beliefs in an interview with the Pittsburgh Tribune-Review (April 23, 2005). "I'm a libertarian," Barry said. "But that's kind of an easy stance to be if you're a humor columnist, because you're tending to make fun of the government and the powerful.... I'm sort of a soft-core libertarian in that my compass is generally pointing away from 'Let's let the government do this'... Does it matter to me that it's Democrats who think we need more elaborate programs that involve shifting money from one group to another group or it's Republicans saying we need to take a harder look at what kinds of things people are watching on cable TV? Neither one of those things strikes me as a good idea."
Here's the complete Reason magazine interview, if you're interested. Here's a highlight:
Reason: In your column I detect a certain skepticism at the notion that congressional spending creates jobs.
Barry: Of all the wonderful things government says, that's always been just about my favorite. As opposed to if you get to keep the money. Because what you'll do is go out and bury it in your yard, anything to prevent that money from creating jobs. They never stop saying it. They say it with a straight face and we in the press will write that down. We will say, "This is expected to create x number of jobs." On the other hand, we never say that the money we removed from another part of the economy will kill some jobs.
Reason: Have you ever had a government job?
Barry: No. I'm trying to think of what government job I would want. Maybe a disgruntled postal worker.
Reason: What's the most ridiculous government program you've ever written about or heard of?
Barry: I would really have a hard time just picking one. Anything at all in West Virginia is a good place to start. My favorite ones are when our own Defense Department says, "No, we really don't want you to build these weapons systems." Where do we stand now with the BI Bomber? We're going to build them but not put wings on them? We call it defense spending, but I wonder why we don't just hand the money to Lockheed and let them go out and spend it and not build a plane that might crash and kill somebody.
I don't think the press has done a very good job dealing with government spending. The Defense Department with the $9,500 toilet seat, that' s not the problem anymore. Medicare and Medicaid and Social Security are the problem. That's us. That's our generation. There the press never says a word.
We certainly never require politicians to ever address those issues except really briefly sometimes during the New Hampshire primary, and then everybody falls asleep.
And here's a YouTube of Dave Barry on Free Speech.