The political satirist often faces a paradox: The best of times for the satirist may be the worst of times for others.

Which brings us to Barry Crimmins. Crimmins — former booker for the legendary Ding Ho comedy club in Cambridge and Stitches in Boston, now writer for Air America Radio — returns to the Boston area for a weekend at Jimmy Tingle’s theater with folk singer Bill Morrissey.

"We both have some righteous indignation for how the little guys gets screwed in this world," Crimmins said of Morrissey. "He might not sign off on all of my politics. But I surely will sign off on every piece of music he’s ever written. You’ll see me pitch a semiarticulate fit that’s got some laughs in it, I expect."

He said this weekend’s shows felt "like a vacation" compared to writing for a four-hour daily radio program and working on an Air America book. "It’s hitting a real sweet spot for me. Unfortunately, the better things are for me, the worse tings are for a lot of people," Crimmins said. The Bush administration’s $100 rebate proposal to combat sticker shock at the gas pumps was just the most recent example. "Wow! A hundred dollars," he said. "They’d give us all a hundred just so we could fill up our tank once. But just to be fair, they’d give the oil companies Alaska! They just keep filling my fish barrel every day."

How did you think Stephen Colbert did handling the White House press dinner speech? "I thought Colbert did a helluva job. In the best spirit of Mark Twain, he proved that no authority can outstand the power of ridicule," he said. "It’s at the point now (Bush) won’t show up to another one of these things unless they hold it in Branson (Mo.)." Crimmins said the press corps hasn’t always done its job. "I loved watching that daily (White House) press briefing every day, because it was getting better. They were asking better questions. As for the dinner…that’s always been phony. Truth makes good humor. I’m pretty sure that now that they’ve called Colbert, they won’t be calling me next year." (Note: The following year, impersonator Rich Little handled the White House press banquet speech)

How do you look back on the Ding Ho now and your role in elevating the Boston comedy scene? "I probably don’t idealize it as much as a lot of people do, because I had to do a lot of the work. The Ding was a great place, it was a wonderful moment," Crimmins said. "We really put Boston comedy on the map. But we also created a lot of innovations. We booked people in advance. We at least let them know how much they could make…if not more…they could live and survive and become professionals. Being a comedian is a great job, but it’s a stupid hobby. It’s a horrible hobby. Especially for the comedians who have to hang around the hobbyists."

"Boston is still a great place for comedy. The Walsh boys have proven that," he said. "It’s a great way to make my way through this world. And I’m completely appreciative of being allowed to do it. I do what I want to do. I’m encouraged there’s some great young acts around town right now. There’s sparks all over the place. The Walsh Brothers, especially, it’s encouraging to see what they’ve done. Bill (Morrissey) will do the same thing with me, scouting out the young musicians. It’s fun to first have a sense of that history, then to begin to become wound up in it, get to work with people…so many musicians have been great to me and introduce me to their audiences. So I don’t have to work Yukheads and do one-nighters and sleep in the condo. It’s tremendous and it continues to be tremendous."

Crimmins said he tries to inform people in a way that encourages them to participate in the civic process as much as they do the cultural process. It’s not all just about American Idol. How can people grade the arts, he wondered. "Rembrandt gets three stars and Gauguin gets four stars…Gauguin wins! And I thought Rembrandt was going to win!"

Crimmins and Morrissey aren’t looking for grades or votes, just laughs. "I haven’t seen him in years," Crimmins said. "And his lawyer girlfriend will be in town, too. I haven’t met her. But it’s always good to have one lawyer on the premises, so we can post bail."