How Jolene’s is changing the tune in Sydney’s live music scene

What began as a small bar with big ambitions has grown into one of Sydney’s most reputable live music venues. In just three years, Jolene’s has carved out a loyal following and a distinct identity – not just for its expansive collection of American whiskey, but for the calibre of artists it attracts week after week.

For those who haven’t experienced it yet, co-founder Simon Rose-Hopkins describes Jolene’s as a Nashville bar in Sydney – the home of cocktails and country.

“Right now we’re Sydney’s only dedicated modern country music bar, and one of I think 10 in the country. We definitely call ourselves a grassroots venue – in 10-15 years’ time we have no doubt we will see some of our current acts doing some big things and be able to say that they got their start at our venues.”

Jolene’s finds its voice

What now feels like an established hub for country music in Sydney began as a leap of faith. It was built from scratch by Simon and co-founder Lucille Rose-Hopkins, with a deep belief in live music and a vision of what it could bring to the city.

“Ahhhh, it was very much a ‘if you build it, they will come’ situation,” Simon recalls, and in the three years since opening that belief has proven true. These days, you’ll see the venue hosts meet-and-greets for the likes of major international artists such as Jordan Davis and Wyatt Flores.

“Having Wyatt Flores perform for the first time in Australia on our little stage was a huge moment for us, that was a huge pinch me moment. I think I actually did have a couple ‘holy shit’ happy tears during the event,” Simon recalls.

“He sang five songs and then hung around to talk to every single fan that wanted a photo, then three days later he played at CMC rocks in front of 23,000 fans.”

Having now caught the attention of major record labels, Jolene’s has also hosted record launches for Troy Cassar-Daley, Brad Cox and Sara Berki.

“Lucille and I both coming from the brand ambassador world before opening the venues means we understand the importance of these events and take them seriously to ensure it’s always executed at the highest standard,” says Simon.

Running a country music powerhouse

Running live music four nights a week – from Thursday through to Sunday – is no small feat. It takes serious planning and a deep understanding of what works for both the artist and the venue.

When Jolene’s first opened, bookings were managed by an external agency, but it quickly became clear that no one would care more about the music than the team themselves, and just three months in Simon took over the programming.

“Having the right artist on the right night of the week can make or break our week. We now have a very strict screening process to make sure that the acts we book always hit the mark,” he told Bars & Cocktails.

But it’s not without its challenges.

“Instead of worrying about a bartender wanting a Saturday night off, I’m worrying about whether that artist is going to pick up a support spot on a tour, or whether they’re going to get sick two days out and not be able to sing.

“Our whole ethos is to treat our artists like we treat our staff. What I mean by that is sometimes things happen, sometimes they may get sick, or they may have an amazing chance to further their career. We are always supportive of our artists on our regular roster, we have their backs like we have our staff backs. It’s down to me to always ensure we have a deep enough pool of talent that we can fill last minute holes, but also ensure we have a solid amount of spots that it’s more than just a once a month gig.

“Something Lucy and I are also really big on is paying them on time, and quickly. Our staff wouldn’t wait up to 4 weeks to be paid, so why should our artists?”

At Jolene’s, programming isn’t just about filling dates. It’s a careful curation of artists that reflect the venue’s roots in country, and a balance of commercial elements with cultural and community value.

“It’s all about balance and understanding an artist’s needs,” Simon explains. “A lot of the artist fee is because they have to bring a lot of equipment to gigs, it’s something we realised before we even opened the venue due to my experience running venues like Surly’s American Tavern and a brief stint at the Lansdowne.

“We have full production capabilities at the venue – have a look at the stage right now, everything on the stage is ours, the drum kit, microphones and stands, guitar and bass amps, everything, this makes it super easy for the artists to play at the venue.”

Big names and a bigger vision

The recent run of high-profile bookings has elevated Jolene’s reputation far beyond Sydney’s country scene. It’s been a game changer for the venue, and with that success has come a broader recognition that Jolene’s is no longer just a local bar, but a serious player on the national live music map.

“People always come up to Lucille and I say they are from interstate or some super regional town and that they have wanted to visit the venue for a long time and that they have been following us for ages.

“We even launched our online merch store because we sell out of our merch so quickly… It’s pretty bloody cool to see where some of the merch is going, never in my life would I think we would get an order from a tiny little town in Northern Territory. Or Texas either!”

And as much as big name country stars turn heads, Simon remains equally committed to supporting emerging and local talent.

“Sure it’s amazing hosting huge names, but we want to look back in 10-15 years and say that we gave the next Brad Cox or Luke Combs one of their first gigs on our humble little stage. We’re not just a gig venue for them, our space is always available outside trade if they want a rehearsal space or if they need a film clip or somewhere for a photo shoot, it’s always available free of charge. If venues don’t support emerging artists, what’s the point?”

Nonetheless, with Jolene’s hitting its stride, that momentum paved the way for Lucille’s – a chance for Simon and Lucille to take their vision to a more intimate space just around the corner.

“If Jolene’s is all about country and western, Lucille’s is all about rock and blues. It’s our homage to some of our favourite Texas dive bars,” says Simon.

“Whilst Jolene’s is more of a cocktail bar, Lucille’s is definitely more of a laid-back dive bar. We have a dance floor that goes off every weekend, cheap beers, and friendly, no-nonsense southern hospitality. Being in such close proximity to Jolene’s, it’s great for guests to spend an entire night in our corner of the CBD, starting with cocktails and live music at Jolene’s, and ending with a beer and a boogie at Lucille’s.”

And the vision doesn’t stop there. “We have some big things planned over the next few years,” Simon tells us. “Bigger! We need bigger! We’re looking to move both concepts into bigger venues. We would also love to host some pop-ups in regional areas,” he concludes.