When playing Monopoly, my father was always determined to acquire Old Kent Road and Whitechapel, and to build on them as soon as possible. It's the most modest portfolio on the board. "You might laugh," my father would tell us in baleful tones, "but everybody always lands on Old Kent Road."

I'm interested in the OKR as a sort of social counterweight to Hampstead, but my friend David, a south London partisan, is genuinely keen on it, and gave me a guided tour this week.

"When the evening sun's like this," he said cheerfully, as we skirted a sofa that had been thoughtfully set out on the pavement, "it's got a sort of I'm-in-a-scary-part-of-LA charm." We were walking past the OKR's array of cosmopolitan food shops, beauty parlours, international cash-transfer places, evangelical ministries and van-washing businesses. As the cars screamed by, David would stop every now and again to photograph lowering clouds over some light industrial unit or brutalist block of flats. He seemed particularly taken with the flyover at the southern end of the road. "A friend of mine owns a flat that looks right on to that," he said enviously.

I looked at a price list outside one of the pubs: it advertised a cocktail called a Slippery Nipple, consisting of sambuca, Baileys and grenadine. You could have a jug of Slippery Nipple for £12.50. Another sign forbade entry to anybody wearing a hat. You knew there was some insight into human behaviour behind this, and that it had been won the hard way.

"If Dickens were alive today he'd be down here all the time," said David as a car came crawling noisily down the OKR with only two of its tyres inflated. David then attempted, with windmilling arms, to direct the dazed-looking driver to a sprawling nearby depot called Madhouse Tyres. As he did so, I reflected that the OKR does have the look of suburban Los Angeles or Chicago - that rangy wildness - and it occurred to me that this is what happens to British streetscapes when middle-class vigilance is reduced and planning controls relaxed: they begin to look American.

David pointed out East Street, which runs off the OKR. Its market features in the opening credits of Only Fools and Horses, the sitcom in which Rodney and Del Boy inhabit a tower block inevitably called Nelson Mandela House. David took me to Mandela Way, which intersects with OKR, and where there is a small patch of green space occupied by a tank that has been painted pink and decorated repeatedly with the stencilled word "scab".

"If this was north London," I marvelled, "there would be letters in the Hampstead and Highgate Express every week until it was taken away." "Really?" said David, snapping away. "It's been here for years."

In the streets off OKR, you never know what you'll find: a battered-looking semi-detached with an ice-cream van parked in the front drive and a lone security camera staring at it; a tiny house with a sign saying, "This property is protected by guard dogs" - that's dogs, plural; sudden bomb-sites with rampant buddleia, the scars of the Second World War seemingly still fresh. There are also surprising runs of pristine Georgian and Victorian houses with obviously middle-class occupants.

You could argue that OKR is going upmarket. The famous old Dun Cow pub is now the Dun Cow Surgery, and the Thomas a Becket, the even more famous boxing pub, built on one of the many sites where the Canterbury pilgrims took liquid refreshment, is now an estate agency.

"You'd think there'd be a plaque acknowledging what it used to be," I said to David. But he frowned and shook his head. "That's one of the great things about the OKR," he said as we trudged on - "a profound lack of sentimentality."