OutPastMidnight (Jay Post & Jimmi Gordon) is a Southside Chicago hip hop duo known for their powerful storytelling, genre-blending sound, and emotionally charged live performances. Their music merges rap with elements of spoken word, soul, funk, and alternative influences, creating an immersive and socially resonant listening experience.

 

Since forming in 2019, OutPastMidnight has become a rising force in Chicago’s music scene and beyond. They’ve performed at prominent venues such as Reggies Rock Club and Gman Tavern, collaborated with organizations including Social Works and the John Walt Foundation, and appeared at major festivals including Lollapalooza (2022 & 2023), Riot Fest 2025, and From the Go Fest 2025, where they opened for Chicago legend Twista.

 

Their growing impact is reflected in an expanding audience of over 17,000 listeners on Spotify, as well as notable sync placements. Most recently, their single “Ear 2 the Streets” was featured in Tyler Perry’s film Duplicity, marking a significant milestone in their artistic and commercial reach.

 

In 2026, OutPastMidnight continues to gain recognition, earning a 312 Music Awards nomination for Best Duo of the Year. As part of the OPM collective, they are committed to amplifying underrepresented voices and creating music that speaks honestly to lived experiences—bridging art, culture, and community.