Jam Sessions

Every week, The Speakeasy transforms into the Upper West Side’s home for live, spontaneous jam sessions.

The Westside Sessions

Every Wednesday night, The Speakeasy becomes the Upper West Side’s home for improvisation and discovery. The Westside Sessions are led by Grammy-winning saxophonist Peter Brainin, whose storied career spans collaborations with jazz legends and performances on international stages. His energy, sensitivity, and commanding presence set the tone for an evening rooted in jazz tradition but never limited by it.

Regularly joining Brainin are two powerhouse musicians: Luques Curtis on upright bass and Gary Versace on piano. Curtis brings world-class groove and modern fire, anchoring the room with impeccable time and an unmistakable voice on his instrument. Versace adds exhilarating harmonic depth and fearless spontaneity, driving musical conversations that keep both the band and audience leaning in. Each week also welcomes surprise guests from New York’s thriving jazz community—rising stars, seasoned pros, and touring artists in town for one night only.

The result is a session that feels intimate, electric, and unmistakably New York. Whether you’re a musician ready to jump in or a listener craving the thrill of live jazz at its most alive, The Westside Jam Sessions invite you to be part of the moment. Come early, grab a drink, and let the music lead the way.

Vibe Check

A weekly Thursday session at The Speakeasy, the hidden room beneath Gin Mill on the Upper West Side. Neo-soul, hip-hop, and jazz — fully live, no cover. A curated night: a resident band plus invited guests, three sets, vocalists and MCs welcome. Hosted by David Engelhard (keys/sax) with Amira B (vocals), Aleksi Glick (guitar), Jon Toscano (bass), Stephanie Young (trombone), and Dan Fernandez (drums).