Flyover Comedy Festival Turns St. Louis Into a True Comedy Destination With the Sklar Brothers and Major Headliners

The Flyover Comedy Festival is back for its eighth year, and St. Louis is fully embracing its growing reputation as a destination for comedy lovers. Running November 13–16 across venues throughout the city, the 2025 edition features major names such as Aziz Ansari, Dulcé Sloan, and hometown favorites Jason and Randy Sklar, better known as the Sklar Brothers. The festival continues to expand each year, and its founders—Zach Gzehoviak and Brady McAninch, who launched it in 2017—have built it into one of the Midwest’s standout comedy events.

You can find the latest details on the official Flyover Comedy Festival website: https://www.flyovercomedyfest.com.

For the Sklar Brothers, this year’s festival represents both a professional highlight and a meaningful homecoming. The identical twins discovered their love for comedy while growing up in St. Louis, where being twins in the 1970s naturally drew attention. Jason Sklar recalls how their unique dynamic made people notice them early on, saying that the novelty of twins—and even something as simple as a double-wide stroller—made them stand out. That constant attention helped spark their fascination with making people laugh and connecting with audiences.

After leaving St. Louis in 1990 to attend the University of Michigan, the brothers further refined their comedic style. At the time, St. Louis didn’t offer the kind of opportunities the comedy industry demanded, so once college ended, they faced the classic choice between New York and Los Angeles. They opted for New York first, drawn to the city’s intense energy and dense comedy scene, and later settled full-time in Los Angeles. Even so, Jason says they still feel shaped by their Midwestern upbringing, noting that they carry a St. Louis attitude with them despite having lived in LA longer than they ever lived in Missouri.

This year, the Sklar Brothers return to headline the festival for the second time, bringing their signature fast-paced banter and what they jokingly call “twin-tuition.” They have two main performances scheduled: 9 p.m. on Friday and 7 p.m. on Sunday. Along with their stand-up sets, they’re hosting “Tag It!”, a show where comedians perform live sets while the Sklars write new tags—short joke extensions—and pitch them onstage. Jason describes it as a blend of improv and punch-up writing, giving the audience a behind-the-scenes look at joke development.

They’re also bringing their popular podcast “Dumb People Town” to the festival stage, joined by co-host Daniel Van Kirk. The show focuses on bizarre, often unbelievable real-life stories—frequently from Florida—highlighting the humor in everyday misjudgments and questionable choices. Jason calls it a “glorious romp through dumb behavior”, joking that it’s their way of pushing back against the increasing absurdity of the world.

Outside their festival duties, the brothers plan to fully enjoy their hometown. They’ll be staying at their family house, sleeping in their old beds, and revisiting local favorites like Ted Drewes, where Jason especially looks forward to his go-to pistachio concrete with extra Heath. Between shows, they intend to introduce their friends to the city’s offerings and revisit the places that shaped their early lives.

With its steadily growing lineup and national attention, the Flyover Comedy Festival continues to redefine St. Louis’ place in the comedy landscape—turning what was once considered “flyover country” into a must-visit comedy hub.