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A few years ago, American author John Koenig invented a word to describe the sense of nostalgia for a time or place you’ve never known: anemoia. I’m sure we all suffer from anemoia in some form or another. The history buff who daydreams about hanging out with Marc Antony at the Forum; that Francophile mate who’s never travelled further than Toowoomba but keeps banging on about Provence.

I have anemoia in spades for mid-century New York supper clubs. God, they look like a bloody fun time. Martini-drenched basements where you would come for a prawn cocktail and stay for George and Ira Gershwin. There was prime-rib, Old Fashioneds, crudites and crushed velvet. Oysters. Cocktail forks. A lot of iceberg lettuce.

I’ve also got a fair whack of nostalgia for Hollywood grills, so when Swillhouse (the team behind Restaurant Hubert and Le Foote in the CBD) announced plans for a live-music venue inspired by supper clubs and Los Angeles steakhouse Musso & Frank, it was cause for some excitement.

Isobel Whelan-Little – a talented chef last seen draping figs in cured pork loin at Chippendale’s LP’s Quality Meats – would be leading the kitchen. Happy days.

Caterpillar Club opened in a low-lit basement near Martin Place in December, curving underground like the letter “C” (or, you know, a caterpillar). The 200-seat lounge was previously a strip joint and, where there was once smoke and ceiling mirrors, there are now frilly light shades and red leather booths. There are 10,000 records for DJs to choose from, and the long (very long) bar rarely has a free seat.

Sydney artist Allie Webb has painted bold murals that would be at home in a 1970s Spanish nightclub, but it still all feels very Sydney. A distillation of the city’s glamour and grunge.

Frustratingly, you can’t book and, on Friday and Saturday evenings, there’ll almost certainly be a queue. If you’re in a group and want a booth, aim to arrive at 4pm when the doors open. Couples are best served by two-seater high-tables, or a drink in the Bamboo Lounge, a secret-ish tiki bar towards the back of the room. With fewer people vying for the bartender’s attention, the cocktail quality here is usually a step up from the main bar.

Unlike the white-napkin supper clubs of my niggling anemoia, there’s no silver service and you have to order at the bar, but caviar and waffles ($175) are available until 3am, plus $950 bottles of 2013 Dom Perignon (much cheaper sparklings are offered).

North America’s most American salad, the Waldorf, makes an appearance with red velvet lettuce, candied walnuts, pickled celery, dill and a restrained use of anchovies ($18).

It’s nice to have to cut through a weapons-grade, smoked cheeseburger ($32) loaded with dry-aged beef, cheddar and soft, sweet onions. On one visit, I wondered if it’s the best burger in Sydney. On another, it was so over-seasoned we couldn’t finish it.

Flank steak with peppercorn sauce and beef-fat chips ($45) was a salty old slog, too.

Whelan-Little recently took over the pans at Swillhouse’s Alberto’s Lounge, and Caterpillar Club’s consistency may have suffered while she runs between kitchens. But when the food’s good, it’s very good indeed, such as those long-flavoured chips, and a cheesy, sharp, tuna-melt sandwich ($22) with satisfying crunch.

Little spanner crab, avocado and lettuce cocktail boats (two for $26) with pickled daikon are wonderfully savoury; empanada-style mozzarella, feta and spinach hand pies (two for $18) are suitably golden and flaky.

Oysters Kilpatrick gets a nod by way of four Sydney rocks ($28) roasted with bacon and smoked bonito vinegar – delicious with a Zombie Highball of apricot brandy, rum, pineapple and eucalyptus soda.

Most house cocktails are pre-batched and cost $25, as does a standard-serve negroni. This has attracted some online criticism. But god knows what the bar line would be like if some drinks weren’t made earlier in the day.

There’s no door charge for the live music; I’d pay a bit extra per drink if it comes with Afrobeat, jazz, funk and soul.

Caterpillar Club is far from the dinner-and-a-show supper clubs of Jackie Kennedy’s New York, but this isn’t a bad thing. Nostalgia is a dangerous beast when it’s overfed.

Better that Sydney has a singular new bar where you might find yourself eating steamed toffee pudding ($20) at midnight and watching experimental disco or a new-wave percussionist.

Arrive early. Stay late. Have a dance. Enjoy your sandwich.

This review was originally published in Good Weekend magazine