Cowboy Karaoke and Late-Night Sets in Downtown San Antonio: What's on at Howdy, Sore Loser This May

TL;DR

•      Howdy, Sore Loser runs karaoke with DJ Ed Perez five nights a week: Monday, Tuesday, Thursday, and Sunday downstairs from 9:00 PM.

•      Thursday is Cowboy Karaoke -- the signature HSL night with a Texas country-focused setlist.

•      Fridays and Saturdays: DJs spinning both upstairs and downstairs starting at 9:00 PM.

•      Private and corporate bookings available for May -- reach out at 210-823-7748.

•      Located at 302 E Commerce St, Downtown San Antonio.

May in Downtown San Antonio means longer nights, warmer air, and a reason to be out late. At Howdy, Sore Loser, we keep things straightforward: good music, a great crowd, and a vibe that never takes itself too seriously. Whether you are a regular who knows every word to every George Strait song, or you are just rolling through town for the weekend and looking for somewhere to land, HSL is the place.

Here is what May looks like at 302 E Commerce St. Come as you are.

Monday, Tuesday, and Sunday: Karaoke Downstairs with DJ Ed Perez

We run karaoke downstairs most nights of the week with DJ Ed Perez behind the board, and we are not apologizing for it. Karaoke at HSL goes from 9:00 PM to 2:00 AM on Mondays, Tuesdays, and Sundays. That's right, even Sunday.

Monday and Tuesday nights have developed a loyal following, particularly among the local service industry crowd who are finally off the clock and ready to unwind. If you want a microphone and a room full of people who are genuinely there for a good time, this is your spot.

Thursday Night: Cowboy Karaoke (The Main Event)

Thursday at HSL is the night that defines us. Starting at 9:00 PM, DJ Ed Perez hosts Cowboy Karaoke downstairs with a setlist built around the songs that built this region: George Strait, Waylon Jennings, Willie Nelson, and the modern Texas country artists that are making new fans every day.

It is loud, it is proud, and it is 100% San Antonio. First-timers always leave talking about it. Regulars never miss it. Come on a Thursday and see what the fuss is about.

Friday and Saturday: Two-Floor DJ Sets All Night

When the weekend kicks in, HSL goes full vertical. Every Friday and Saturday at 9:00 PM, we have DJs spinning both upstairs and downstairs. Two floors, two distinct energy levels, one very fun problem of deciding where to be.

The downstairs floor is where it gets rowdy. Upstairs gives you a slightly elevated view of the night with room to breathe and a great angle on the crowd below. Most people end up bouncing between the two, which is exactly the point. May weekends here fill up, so come early if you want a spot to settle into.

Bring Your Team: Corporate Events and Private Bookings

Skip the hotel ballroom. Howdy, Sore Loser is built for groups who actually want to have a good time together, not just stand around in a conference room with a cheese plate. We are seeing a strong push for corporate bookings in May, and our layout makes it easy to host everything from a casual department happy hour to a full private takeover.

1.    Private Downstairs Karaoke: Reserve the downstairs stage for your own private Cowboy Karaoke tournament or custom-themed karaoke night.

2.    Upstairs VIP Mixer: Keep your group together in an elevated setting while staying connected to the downtown energy below.

3.    Full Venue Buyout: Take over all of HSL for your event, both floors, full bar service, and a team that knows how to run a high-energy night.

We are right in the heart of the downtown district at 302 E Commerce St, which makes us a natural fit for any team coming down from the San Antonio or Austin corridor looking for a night that is actually memorable.

Reach out to lock in your May date before things fill up: 210-823-7748. No pressure, just come hang.

Howdy, Sore Loser | 302 E Commerce St, San Antonio, TX | 210-823-7748