XL Fest was founded by Troy Pryor, as an extension of Creative Cypher’s live event series and XL Content Lab in 2023 to help emerging filmmakers gain access to long-term career opportunities beyond traditional film festival exposure. Pryor believed creators needed more than screenings, they needed a sustainable pathway connecting development, industry access, distribution, and cultural visibility. To help build that vision, Pryor partnered with Michelle Kennedy, whose Chicago South Side Film Festival was absorbed into Creative Cypher, helping form the foundation for XL Fest. Kennedy remained on as Interim Executive Director during the inaugural year, helping secure early funding and operational support.

From the beginning, XL Fest positioned itself as more than a traditional film festival. Designed as a launchpad for creators, brands, and institutions, the festival became the public-facing platform for talent emerging from XL Content Lab while creating opportunities for collaboration, entrepreneurship, and industry connection. The inaugural festival featured legendary filmmaker Robert Townsend alongside Louis Carr, President of BET, as keynote speakers, signaling the festival’s national ambitions from day one.

The following year, acclaimed actors and producers Larenz Tate, Lahmard Tate, and Larron Tate headlined the festival, further elevating its national profile. Following their involvement, the Tate brothers joined the XL leadership ecosystem to help expand the festival’s reach, industry relationships, and star power. As Creative Cypher expanded, Pryor continued scaling XL Fest through year-round programming, strategic partnerships, and cultural activations including the Robert Townsend Experience and collaborative programming with Soho House.

Today, XL Fest has grown into one of Chicago’s emerging signature cultural festivals with national reach, supporting tourism, workforce development, and Chicago’s creative economy while positioning the city as a hub for storytelling, innovation, and creator-driven collaboration. What began as a platform to showcase filmmakers has evolved into a growing cultural ecosystem designed to create long-term opportunities for the next generation of creators.