Jaime De Leon says community organizing inadvertently prepared him to do stand-up comedy. He already had a sense of humor and a bright voice to go along with it, but he learned to speak to large groups of people comfortably by doing advocacy work, like giving citizenship classes, merging block parties and sports through a youth program called B-Ball on the Block, and helping to rally for a new high school in his neighborhood of Little Village.
Jaime was part of the effort that, almost twenty-five years ago, pressured the city to build an entire campus, Little Village Lawndale High School, after a nineteen-day parent-led hunger strike. He describes his role as canvassing and holding planning meetings for community members to participate in designing the four schools that would serve all of Lawndale.
As the Latinx comedy scene in the city continues to develop, Jaime has been instrumental in carving out a space for a brand of Mexican American humor that was relatable, accessible, collaborative, and Chicagoan. “I didn’t know anything about stand-up,” he said, but he had this urge to share funny stories that he had experienced or witnessed personally.
He and his friends had been frequenting Martin’s Corner bar in Heart of Chicago when he decided it was time to get up on stage. “One day I see they’re having an improv comedy sketch group,” he said, and he wasn’t amused. “It was a total of like ten people, like these friends performing and their friends watching… Had never seen them before, they were all white, though. I told myself, if they’re gonna let these guys perform, they gotta let me do some stand-up.”
I remember reluctantly going to Martin’s around 2012 for the first time after hearing there was a benefit event for DACA recipients. It was one of Jaime’s first stand-ups. What brought me back to his shows, aside from the themes of his comedy routine, was that he performed in local venues that were overlooked or, in some cases, stigmatized at the time. I particularly remember going to a performance at Casino Tropical, an aging salón de baile or Mexican nightclub on 26th Street, right before it was demolished.
Jaime would link up with Mike Oquendo, a Puerto Rican comedian based on the North Side who did shows at Joe’s. Jaime considers his “first real show”—with a host, a program, nice seating, and promotion—to have been at Watra Night Club via the Mikey O Show. There, he talked about growing up in Little Village and “living with my mom and being a single dad of a daughter at the time.”
Because it was the right audience, he also poked fun at the Mexican experience, and that has come to characterize his style. One of his jokes is about taking his kid to a company party and being mindblown when they start to hit a piñata with a pool noodle so that everyone gets a turn. He also pushes boundaries with jokes about immigrants having sex that he calls “immigrant porn.”
The fifty-two-year-old comedian has faced challenges in his personal life with the same candor that he does stand-up. He’s a two-time cancer survivor. In January of 2024, he completed chemo and has been in recovery since. His health, on top of COVID, affected his ability to do standup as frequently. He’s also a married father of two boys that keep him busy.
Social media has helped diversify the people and opportunities in the Latinx comedy scene in Chicago, with venues such as Zanies, the Laugh Factory, and the Comedy Bar in River North having more regular Latinx performers and even Spanish-language shows.
He sees promise in the growth of the comedy scene, but also talked about the setbacks of the internet: “So many comics getting booked at comedy clubs… have done very, very little stage time, but they have a massive social media presence and that’s why they get booked. Writing material, performing it, testing it out, and open mics, calling bookers, going on the road, you don’t have to do it anymore.”
Jaime continues to produce shows by having a line-up of guest comedians from all over the city at Simone’s Bar, where he also performs. Called Pilsen Stand Up, he hosts the show every third Wednesday of the month. In June, they celebrated Pilsen Stand Up’s 10th anniversary with co-host Abi Sanchez, followed by a karaoke set with DJ Pablo Serrano.
Pilsen Stand Up, Simone’s Bar, 960 West 18th Street. Every third Wednesday of the month, 8-11pm. $5 cover.