Leather booths, live music and late-night cheeseburgers? Martinis, oysters and fancy fish fingers. You might well say, “Sounds fun, but haven’t we seen all this in Sydney before?” And indeed, yes. But not like this. Head down Caterpillar Club’s stairs just near Martin Place, and you’ll find one of the most exciting basements and bars to grace the city in some time.

What’s the big deal?

It’s the second opening this year from the team at Swillhouse, the hospitality group setting trends since it opened Darlinghurst’s Shady Pines Saloon in 2011, and later Restaurant Hubert, Alberto’s Lounge, The Baxter Inn and Le Foote. Caterpillar Club feels like all those places rolled into one – a bit glamorous, a bit grungy, and very much anything-can-happen.

It also feels like the spiritual successor to Frankie’s, Swillhouse’s perennially packed rock-n-roll den that closed on Hunter Street last year to make way for the Metro West rail line. It’s a lot less beer- and sweat-drenched than Frankie’s, but there will be live music and late closing times seven nights a week. A house collection of 10,000 records, more or less, is waiting for a spin, too.

Why “Caterpillar Club”?

Because the 200-punter capacity venue (formerly Men’s Gallery strip club) curves around like a caterpillar, and “Caterpillar Club” is an excellent name. The plush leather and timber-forward fit-out is partly inspired by classic Hollywood martini haunts such as The Tower Bar and Musso & Grill.

“I think it also feels uniquely Sydney,” says Swillhouse chief executive Anton Forte. “I don’t know anywhere else that has this kind of long bar and super-late liquor licence with great food and live entertainment. There will be a huge range of music, including funk, soul, world and jazz.”

Meanwhile, Sydney artist Allie Webb has contributed vibrant strong-lined murals for just about every bit of wall. It’s a very, very nice place to eat onion rings ($10).

What else are we eating?

Chef Isobel Whelan-Little leads the kitchen and has put together a sharp menu channelling American supper clubs from a time when Clark Gable was the hottest thing since sliced pineapple. Oysters Caterpillar (four for $28) are a nod to oysters Kilpatrick, and “fish fingers” ($24) means two Mars Bar-sized tranches of crumbed blue-eye with yoghurt tartare. Nice one.

The cheeseburger ($32) is one of the meatiest-tasting in town, and it’s always nice to see the tuna melt ($22) make an appearance, along with chips fried in beef fat ($14) and steamed date pudding ($20). For something lighter, there’s a savoury-sweet spanner crab cocktail with avocado in a lettuce cup (two for $26) and Berkshire leg ham with pickled onions ($22).

How much is a negroni?

You’ll pay $25 for the Italian classic (which isn’t cheap, but still less than similar bars in New York or London). Bartender Lello Arzedi’s cocktail list teems with plenty of other delicious things, though, such as a Pina Colada with salted coconut ($28), a banana-enhanced Sherry Cobbler ($24), and a Zombie Highball fizzing with eucalyptus soda ($25).

Where’s the best seat?

That depends on who you’re with and what you’re after. The long (very long) bar is best for solo martini missions, while a row of two-person booths seems engineered for first dates. Larger tables near the small stage suit groups keen for a longer innings.

If we had to pick just one spot to sit, though, it would be the tiki-style Bamboo Room, Caterpillar Club’s semi-hidden bar-within-bar. It looks like somewhere Elvis might drink a hundred daiquiris if he was more into rum and surf rock.

Can you book?

Er, no. Walk-in guests only. Arrive early (or very late) if you want one of those booths.

Open Sun-Thu 5pm-3am, Fri-Sat 5pm-4am.

92 Pitt Street, Sydney, swillhouse.com