Another year, another list declaring Black Star's lamb shank and red wine pie the best pie in Sydney. Well, almost: while we certainly hold a special place in our hearts for pastry man Christopher Thé's most famous savoury offering, his beef brisket and Young Henry's pie has now come along and put up a serious challenge. Yep, Young Henry's, the Newtown brewers taking over taps everywhere in Sydney are now taking over our pies. And thank God: this is an amazingly rich thing to eat. So tender. If you're a neat freak, though, you need not apply. The pastry is soft (the filling moves around every time you touch it, like a water bed) and it's super flaky, too. The whole thing will fall apart quickly, coating your fingers in pastry shavings and braised meat on its way down. We're not fussed. Sitting in a gutter on Australia Street, mess in our hands and flakes on our faces, we couldn't be happier.
These guys know how to handle their beef brisket. In this simple pie it's stewed until all soft – but not mushy – and complimented perfectly with a few slivers of mushroom. We'll take two. And if you don't like your meat so fatty, there's a regular, slightly cheaper beef option. We love that burnt crunch you get on Bourke Street's savoury treats, and you'll find plenty of crunch around the tops of their dark, golden pies. Pair it with a pork and fennel sausage roll – this is, of course, a must on any visit – and hit one of the nearby parks with a bottle of their super-tangy lemonade. The brisket pie here is a good deal cheaper than some of the other pies on this list ($5.30 to Black Star's $7.80) and – bonus – small enough to manageably eat at a footy game, if you're passing through on your way to the SFS.
You know those Edgells cans of mushrooms in butter sauce you might have had on toast as a kid? (What, we were the only ones?) Well, the big, golden steak and mushroom pie at this Darlo bakery brought back some strong memories of those – in a good way. The pastry is firm, and brown; the lid flaky and crunchy. But it's what's on the inside that counts. Here, hunks of super tender beef compete with dark hunks of mushroom in a thick braise. It's a bold flavour, all mushrooms and pepper and good times. We love it. If you're not feeling the mushrooms, there's a regular mince beef number and a damn good quiche Lorraine with a full, hard-fried egg buried inside. And their pain au chocolates are worth a look, too.
Sydney's most la-di-da pie shop has a lot to recommend it – who doesn't love eating your pie in a loft-like space with a glass of wine or a craft beer? And if you like your fillings experimental, you've come to the right place. Behind the glass display case up front you'll find pies like mountain venison, spicy Nepalese lamb curry and chicken carbonara. We break our 'simple beef pie only' rule for a pie filled with roasted duck, mushrooms, carrots and spinach in a very sweet maple syrup and Cointreau liqueur sauce. Let's just say some rules are not meant to be broken. And when the Pie Tin's simple chunky steak and stout pie is this good, why would you? It's a deep thing with firm pastry, crumbs on top and a beery beef casserole inside – tender chunks, stewed onions and a pub-pie vibe. Careful though, this thing is damn hot: proceed with caution if you value the roof of your mouth.
The Northern Beaches' favourite little mom-and-pop pie store has a big upper hand in Sydney's pie wars: Collaroy Beach. Once you pick your pie from the small shopfront with the large line out front, cross Pittwater Road and march down Anzac Avenue and enjoy it by the seaside. It's one of the prettiest spots in Sydney. But the pies here would be worth the trip even if you had to eat them in an alley, really. There's enormous range, and some adventurous flavours – a chicken, avocado and brie number is surprisingly good – and their signature beef and Burgundy is grand stuff. The beef chunks could be tenderer, but that thick Burgundy sauce they're swimming in is winey perfection. Bonus points for manageability, too: the pie is small enough to hold and the no-fuss, crisp, not-too-flaky shell makes for quick, easy, beach eating.