When we rolled into Cadillac Jack’s on November 14th, we honestly weren’t sure how an acoustic duo would go over in a place that leans hip-hop and dance. We tuned up, crossed our fingers, and hoped our set lists would land. By the end of the night, we were grinning at each other between songs, because it was clear: they were in.
Figuring Out Cadillac Jack’s
Cadillac Jack’s in Bloomington, IL has a lot going on in one room—multiple bar areas, TVs, and a big dance floor that clearly sees a lot of late-night action. Their stage is set up so you can actually see people’s faces instead of just silhouettes, which makes a huge difference when you’re trying out slower songs or taking requests.
As we finished soundcheck, we both had the same thought: this might not be “our” crowd on paper, but we were curious to see what would happen.
The Crowd That Wasn’t Expecting an Acoustic Duo
The room filled up with a pretty mixed crowd—people who came for the DJ, people hanging at the bar, and a few who clearly just wanted to dance to whatever was loudest. Even so, they gave us a real shot. We could feel it after the first couple of songs.
At one point we slowed things way down with “Slip Slidin’ Away.” It’s not exactly a club banger, but when we hit the last chord, the applause was big and genuine. That was the moment we relaxed a bit and thought, “Okay. They’re with us.”
Requests, Surprises, and a Guest Named Yo
Once everyone realized we were taking requests, things got interesting in the best way. Here are a few of the moments that stuck with us:
- Neil Diamond fans came out of the woodwork, calling out classics from across the room. We did what we could on the spot and even found ourselves promising a Steely Dan tune for next time. Now we actually have to learn it.
- A local singer named Yo hopped up with us for “Tennessee Whiskey” and “Come Together” by The Beatles. We hadn’t planned on sharing the mic, but the crowd leaned in, phones came out, and it turned into one of the standout parts of the night.
- We wrapped the set with upbeat songs like “Stuck in the Middle With You” and “Mustang Sally,” which turned out to be the perfect handoff to the DJ’s Saturday Night Club Vibe. By the time we were packing up, the dance floor was already shifting gears.
One of the bouncers summed it up for us on our way out: “I didn’t think that kind of music would work here, but you guys won them over.” Hearing that from someone who sees every kind of night in that room meant a lot.
We also had a great conversation with Miranda, the bartender, who said she’d like to have us back. We don’t take that lightly—bartenders see and hear everything, so that kind of feedback goes straight to the top of our mental highlight reel.
Post-Show Taco Bell and Looking Back
After we loaded out, we did what any self-respecting musicians do at the end of a long show: hit Taco Bell. Over burritos and whatever we could get our hands on quickly, we replayed the night—the surprise requests, Yo jumping in, the way “Slip Slidin’ Away” somehow worked in a club setting.
We also grabbed some solid footage of Yo singing with us, and we’ll be sharing that soon. It’s the kind of thing you can’t really plan, and that’s exactly why we love it.
Come Hang With Us Next Time
Our night at Cadillac Jack’s reminded us how fun it is to walk into a room that isn’t “built” for acoustic music and win people over one song at a time. We’re looking forward to getting back there and seeing what happens on round two.
If you’re putting together an event and want live music that can roll with the unexpected—taking requests, adapting to the room, and keeping things genuine—book us for your next event.
Here’s to more nights where we plug in, read the room, and see where the songs take us.
