In the threadbare upstairs room that passes for an owner's office at the Lakeshore Theater, original LPs from 1960s comedy giants Dick Gregory and Mort Sahl lean against a window.

Chris Ritter, the club's owner, had bought the records in order to have Gregory and Sahl sign them this week, when they were to play his art house comedy club in a converted movie theater on Chicago's North Side.

Instead, along with the broken and plastic-bag-covered urinal in the men's room, they stand as a symbol of what went wrong at the Lakeshore, which hosted some of comedy's most cutting-edge acts and had Robin Williams show up on its stage more than once, but could never live any better than hand to mouth.

Already reeling from a big loss on a Sandra Bernhard show in February, and faced with more five-figure losses in the weeklong stand by Sahl and Gregory that wasn't selling well, Ritter pulled the plug on the Lakeshore on April Fools' Day.

"Stupid, three-legged dog," he says, comparing the 330-seat theater at Broadway and Belmont to "a pet you have to put down that is deformed in some way, has some sort of terminal illness. But she just looks at you with those eyes."

Ritter, 42, was a theatrical producer who fell into comedy not out of some master plan, but because that, he says, is what worked in the room he has held together "with paper clips and rubber bands" for eight years, the last three as a comedy house.

Letting it go, clearly, is difficult. We are talking in the theater, the afternoon before a raucous farewell show featuring many of the local comics the Lakeshore has nurtured. The seats, he points out, need replacing. The running lights along the aisle went out not long ago, a fire code violation.

"There's just so many mixed feelings," Ritter says, then blinks hard and looks away, down toward the stage where national stars including Jim Jefferies, Demetri Martin, Mike Birbiglia, Maria Bamford, Doug Benson and more found a Chicago home.

Upstairs is the small apartment where Ritter, his wife, Jessica, and son, Joey, now 10, lived for six years. The family hasn't had health insurance for at least three years, and a few months ago, he says, Jessica was found to have breast cancer.

"It really gave me a personal jolt: OK, you've got an artistic mission and you're really dedicated to the place, but what are you really doing with your life?"

He adds: "I know in the core of my heart I'm doing the right thing, for myself and for my family. And I'm utterly convinced that in a month, six months, a year from now, I will have this incredible sense of relief in my life, where I'm not running around, panicked about how I'm gonna cover payroll next week, or whether the plumbing's about to explode.

"What I really want to do is work with artists and do shows. I know that that is going to be my endpoint, so there's a certain comfort in that. But the, uh" — another long pause, another look into the emptiness of a theater in the afternoon — "it's hard."

He repeats the phrase: "Stupid, three-legged dog."

•••

There were final shows Friday and Saturday from Jefferies, the budding Australian superstar whose career arc exemplified Lakeshore's strategy of building an audience for cutting-edge artists. His first show at the theater did $198 in box office in November 2007, and a lot of tickets were given away; his last ones sold out, four shows, some $6,000 per show.

But before Jefferies, on Thursday night, there is "Closing Acts," a hybrid open-mic night/Irish wake/jazz funeral.

For 61/2 hours, two dozen stand-ups take turns eulogizing the Lakeshore, roasting Ritter, taking potshots at the much more conventional Zanies comedy clubs, bemoaning Chicago's busy but undernourished comedy scene and, mostly, because there was a microphone and stage time, doing their own acts.

"Welcome to the end of any hope you ever had," says James Fritz, the night's first emcee, speaking to an audience of mostly comedy insiders.

"I'd be less upset if my parents got a divorce. Honestly, this place means more to me than my blood."

Fritz also suggests that Bert Haas, the executive vice president of Chicago's Zanies outposts, is "dancing a jig" over the closing, the first (and least derogatory) of several mentions of Haas by name.

(Haas, reached by phone, gives it right back. "It's just another venue," he says of the Lakeshore, one whose closing "means there will be other places popping up… I've been with Zanies since 1980. In those 30 years I have seen at least 60 different establishments open, try stand-up comedy and close.")

"Chris Ritter tried to be an artist on top of being a businessman," says Dan Telfer, who runs Chicago Underground Comedy, one of the alternative options that will pick up some Lakeshore slack with local acts. "This place filled a void that the country was lacking, not just Chicago."

At some point the national anthem is sung. After most everyone remaining at 1:30 a.m. gets onstage to sing it again, Roseanne Barr is officially forgiven.

"I called Ritter a couple of weeks ago about opening up for Nick Thune," says the comic Prescott Tolk. "He said, ‘Yes. Do you know anyone who has $200,000?'"

•••

The numbers, actually, were moving in the right direction, Ritter says, bearing out, he believes, the validity of the idea that he and comic Paul Provenza, an adviser, hatched in early 2007: Showcase comedy as an art form (and stop the financial bleeding).

In 2007, the first year as a comedy-only venue, he and his partners lost $404,000, according to Ritter. In 2008, the venue lost $268,000. And last year, as attendance continued to grow and Ritter cut payroll by 55 percent, it actually made a profit, of about $65,000.

But his salary kept shrinking; he took home $30,000 last year, he says. And it seemed there would never be enough to pay down the $200,000 in debt remaining (after his partners covered the bulk of the losses) or give the building the more than $150,000 in repairs he says it needs.

Since the closing announcement, Ritter has been gratified by the support and has come to believe people understood the club's mission in a way he wasn't sure they did while it was running.