Last May local comedy impresario Mike Oquendo got an unexpected phone call. “You know you’re doing the work of the devil,” the caller said. Oquendo realized the man was protesting Proud to Laugh, a gay comedy showcase he’d organized as a fund-raiser for this year’s Gay Games, and laughed.

“We’ll see if you laugh in hell,” the man said.

“If I do go to hell,” Oquendo replied, “I’m gonna open one hell of a comedy club.”

Since 2001 Oquendo has become one of Chicago’s most successful independent stand-up comedy producers–and he’s done it by presenting shows that cater to diverse comedians and audiences. In addition to Proud to Laugh, the 40-year-old has produced shows with titles like Risas y Ritmo, Paisano Comedy Jam, Fajitas and Greens, and Those Funny Irish. Last year he organized 35 shows and he expects to do 60 this year, including open-mike nights and his monthly Cultural Madness Comedy Jam, which manages to pack in crowds at its home venue, Joe’s Bar on Weed Street, even in the middle of the week.

Oquendo, who bears a passing resemblance to Ozzie Guillen, grew up in Wrigleyville. “Back then it was all black and Puerto Rican,” he says. His parents were born in Puerto Rico and moved to Chicago in the 50s, where his father worked as a grocer and his mother as a factory worker. When he was 12 Oquendo’s older sister brought home the Freddie Prinze stand-up album Looking Good. Listening to it and relating to Prinze’s Latino experiences changed his life, he says. “We were poor, so I’d just sit in the living room and replay that album over and over.”

Inspired by the energy of the audience on that record, Oquendo decided at 16 to put together his first public event. He brought together four north-side high school DJs for a competition at Roscoe’s Death Trap, a nightclub at Roscoe and Clark. They all pitched in to cover the $50 rental fee, and 90 kids showed up. Oquendo did it again the next year in a larger space, handing out a thousand flyers he’d designed himself. Five hundred people attended. “Here I was at 17 with $3,000 in cash in my pocket and no clue what I was doing,” he says. “My mother was convinced the money was stolen or ‘misappropriated.'”

After high school Oquendo spent three years in Georgia and Texas as a medic in the army. “I was known as the entertainer,” Oquendo says, “joking around with the troops, getting singing groups together.” He returned to Chicago and eventually landed a job at the city’s 911 call center, where he still works four days a week. (He also produces the office Christmas party, Fire Alarm Follies.) He watched a lot of stand-up and eventually started performing at open mikes in Chicago, but he says the lineups discouraged him. “I saw few African-Americans and no Latinos,” he says. “Those shows just felt out of reach.”

As a promoter Oquendo was faring better. In 1999, after he’d spent several years organizing occasional small-scale entertainment and charity events, a police officer he knew asked for help producing Luna Cabana, a summer music show he was doing at Adler Planetarium. “I did everything from coat check to sound check,” Oquendo says. That experience led to a job as the gala event coordinator for the 2000 Chicago Latino Film Festival. “That’s where I got the bulk of my experience,” he says. “I would sweep and mop the venue floors in the morning, show up in a suit in the evening to host, then take off the suit and sweep and mop again before leaving.”

In the summer of 2000 Oquendo had another epiphany. “I went to a Marc Anthony concert at Allstate Arena and saw a guy named Freddy Soto, a Mexican comic, open for him,” he says. “I remember thinking, this is insane–he’s rockin’ the crowd. This guy has 15,000 Latinos here. I just need 150.” A few months later he started Mikey O Comedy Productions with the goal of presenting multiethnic comedy showcases in a “neutral” location–somewhere downtown or on the near-north side. He immediately got in touch with Alex Ortiz, an old army buddy who’d been dabbling in stand-up, to get him involved. “I expected it to tank like most people’s rooms,” Ortiz says. “Most people don’t have the energy to sustain something like that.”

In 2001 he was asked to serve on the advisory board for the Latin Grammys and host Chicago receptions for local artists and industry big wigs. Though the work raised his profile, Oquendo was still struggling to find a home for his show. He says one owner told him, “We’re happy with our blond-hair, blue-eyed people seven days a week.” Finally, in February 2002, Ed Warm, the owner of Joe’s, showed some interest. Oquendo liked the venue’s midsize capacity and its Goose Island location, but he had very specific expectations. “My goal was always to make comedy affordable,” he says. He insisted on no cover charge, no drink minimum, and wanted the freedom to experiment with new themes and formats. Warm said OK.

The first show, a two-night all-female revue called Girls Nite Out, took place in an outdoor tent the weekend after Valentine’s Day. “I was hoping for 100 each night,” Oquendo says, “but it was completely out of control–300 both nights, and we had to turn away people at the door.” One of the three acts wound up canceling, but Ortiz lent a hand. “So Alex shows up and does a routine as a ghetto transvestite,” Oquendo says. “And he kills!”

After more than a dozen successful shows Oquendo introduced the Cultural Madness Comedy Jam, the showcase he’d always wanted to do, in February 2003. “We used one of Joe’s smaller-function rooms with no stage, no lighting, no budget,” says Phyllis Murphy, the promotions manager at Joe’s. “We literally plugged a mike into a portable system and flew by the seat of our pants.” Around 80 people turned out–better than expected for a Tuesday.

Cultural Madness is now a monthly event and Oquendo’s signature show. Last month’s installment drew 240 people–mostly Latinos, blacks, and South Asians. On the bill were a “100% Irish-Catholic”; an African-American south-sider; a “lesbian born in Bombay and raised in Indiana”; a Sox-loving Chicano from Bridgeport; an Italian-American sporting an Italia track jacket, a gold chain, and a Kangol; and a Pakistani-American who says his first name, Kumail, keeps getting changed to camel in spell-check. A white guy from Cleveland opened.

Oquendo, who almost always hosts his shows so he can do his own comedy–observational humor about family and growing up Puerto Rican in Chicago–brought up audience members for birthday serenades and prize drawings and stayed long after the show to shake hands and talk.

Oquendo advises his comics to “stay away from abortion, rape, domestic abuse, and the word pussy, because those things get you in trouble,” but they appreciate that he doesn’t censor them or ask them to emphasize their race, ethnicity, or sexual orientation. “I think our show is more about commonalities than ‘otherness,'” says Sapna Kumar, who has performed at Cultural Madness since the beginning. “All of the comics have unique experiences that ring some grain of truth on a universal level. That’s why people laugh.”

This weekend marks the return of two Mikey O shows. The fourth annual Cinco de Mayo Comedy Fiesta features two Latino stand-ups and a grito contest. And after the strong turnout at last year’s Proud to Laugh show–which Oquendo says got a lot of support from the local gay community after news of the harassment–he’s bringing the event back as Proud & Loud. Oquendo’s comedy shows have even attracted attention outside of Chicago: last month he set up shows for SYSCO and at Michigan State University. He’s also actively involved in organizing fund-raising and charity events, which he says comprise about 20 percent of his productions.

Leading up to this weekend, Oquendo got another unexpected call–this one from a representative of Brothers and Sisters United for Christ. He worried that Proud & Loud had attracted more homophobia, but it turned out the man was wondering if Oquendo would be interested in producing a Christian comedy show. Oquendo met with members of the organization and was up front about the work he does. “But the bottom line,” he told them, “is that I’m an entertainer. I’m in the business of funny.” He’s since booked three local minority Christian stand-ups for his Comedy for Christ show in August.

“Once I cover that,” Oquendo says, “I will have covered everything.”

Proud & Loud

When: Sun 5/7, 7 PM

Where: Rumba, 351 W. Hubbard

Price: $10

Info: 312-222-1226

Cultural Madness Comedy Jam

When: Sat 5/20, 7:30 PM

Where: Joe’s Bar, 940 W. Weed

Price: $10

Info: 312-337-3486

Art accompanying story in printed newspaper (not available in this archive): photo/Joeff Davis.