Roscoe's Presents: Chicago Entertainer of the Year 2026

Shake off the Monday blues with Danny hosting a night of 90s and 00s music videos, cheap drinks ($5 call it), and the kind of crowd that actually gets it. It's the reset you didn't know you needed — log off and let go from 5pm to 2am.

A regular gathering for people exploring or questioning their gender identity and expression — a space to connect with others who get it, share experiences, and find community with people on similar journeys. Whether you're early in your exploration or further along, this group at Center on Halsted offers the kind of judgment-free connection that matters.

Monday nights at Center on Halsted belong to recreational volleyball players who know the basics and want to keep improving. A welcoming, skill-appropriate environment where you'll actually get good touches and learn the game without the pressure of competitive play. Show up, get a workout, find your people.

A space to explore what it means to be a queer man — processing experiences, redefining identity, and reflecting on the things that shape how you move through the world. This is the kind of honest conversation that happens when you're in a room with people who actually get it.

Monday nights at 2Bears belong to the trivia regulars who show up for free games, cheap drinks, and the kind of banter that makes the whole room laugh. It's unpretentious neighborhood bar trivia at its best—the kind of thing that keeps people coming back week after week.

Musical Monday Show Tunes night takes on a special anniversary glow as Sidetrack celebrates three decades of Jonathan Larson's revolutionary musical. Expect the songs that defined a generation, a room full of people who know every word, and the kind of communal sing-along energy that only happens when a show means this much to this community.