Harry Edwards, by most reports, was a pretty dodgy bloke. The kind of bloke who allegedly sold ground-up rubber as loam soil to rich families. A bloke whose boxing skills earned him the nickname "Tiger" while serving in World War II. A bloke with a sister-in-law who described him as a "real villain" to the Herald in 2014.

Edwards is also the bloke who opened Harry's Cafe in 1945 near the Garden Island naval dockyard and provided Woolloomooloo sailors, wharfies, drunks, socialites, theatre-goers, night-clubbers, cabbies and cops with late-night pies and cups of tea.

The "de Wheels" part of the name came about when the council said street vendors couldn't remain permanently in one spot. Edwards did some investigating and discovered he only had to shuffle the pie caravan 30 centimetres every day. The former fruit-truck driver dutifully set about moving the cafe to the left one day and to the right the next.

Edwards died in 1979, aged 67. However, an Austrian engineer and Port Kembla steelworker named Alex Kuronya had owned Harry's from 1970. Kuronya sold it to Vietnam veteran Michael Hannah in 1988, who franchised the business to open more than a dozen new stores in NSW (and one in Shenzhen, China) before selling to Tino Dees in August. Dees has received numerous awards for his sausage-making skills as the owner of Bexley North's German Butchery.

Not all of the Harry's stores that have opened in recent years are a benefit to the brand's status. Many feel soulless and slapped together – like Hungry Jack's with pies. The Woodbine outpost has a drive-through, for instance. Who wants to eat mushy peas behind the wheel? Thankfully the 'Loo branch still has charm.

Salt spray rusted the first Harry's caravan, donated to the Powerhouse Museum in 1985. The current version does a decent job replicating the original with neon lights and 1950s-style signage advertising pies, peas and Schweppes. On a recent Wednesday night visit it was patronised by tourists and two old boys in singlets hovering around the condiment station salt shakers like moths to a flame.

Let's talk Tiger ($7.80), the cafe's signature creation of a meat pie topped with perfectly serviceable mashed potato, mushy peas and a big whack of gravy. The pie is made by Harry's own bakery, Hannah's, in Ultimo and it's a thick-cased, fist-sized puck of diced topside you can eat one-handed without spillage. The seasoning is en pointe and black pepper provides a backbeat of heat. Are there better pies in town? Sure. But Harry's still does a damn fine job and the Tiger is Aussie street food for all time. It's even better sharpened with a dash of Worcestershire.

I was expecting great things from the Hot Dog de Wheels ($8.10) given Dees' wurst prowess, but the sausage recipe has so far remained unchanged from the Hannah years: a good-enough frankfurt-style snag existing to bear chilli con carne, peas, garlic onions and cheese sauce. The dog is a heavy hound and, while I don't regret finishing it, I can't see myself ordering another one without seven schooners at the East Sydney beforehand.

The menu also lists chips ($3.50/$4.50), a pulled pork roll ($9.80) and apple turnover ($5.90), but unless you're cursed with a pea allergy, I see no reason to bypass the Tiger. There are other places to eat pulled pork in Sydney.

Dees says he wants to continue Harry's expansion by launching in other states, and all power to him. If it's done with care and consideration to the brand's heritage, Woolloomooloo's great unifier can provide the old "dog's eye with dead horse" for many generations to come. What's that old jingle? "We love football, Harry's pies, kangaroos and Holden cars"? Something like that, anyway.

Est. 1945

Signature dishes Harry's Tiger ($7.80); pie 'n' peas ($6.40); curry beef pie ($5.40); Hot Dog de Wheels ($8.10).

Famous diners Sir Elton John, Frank Sinatra, Colonel Sanders, Prince Harry, Kerry Packer, Brooke Shields, Robert Mitchum, Judy Garland, Shirley MacLaine, Arthur Beetson, Clive James, Anthony Bourdain, Billy Crystal, Jerry Lewis, Marlene Dietrich, Eric Idle. Mandawuy Yunupingu, Norman May.