Dallas Penn

The Dallas Penn I knew was always figuring out new ways to use the internet, blogging and vlogging (about Ghetto Big Macs, bodegas, baseball stadiums, sneakers) before blogging or vlogging were much of a thing, and co-hosting a pioneering hip-hop podcast, the Combat Jack Show. He’d come a long way from his stomping grounds but never forgot them or left them behind.

‘I got mixed up in a youth collective back in the 1980s called the Decepticons,’ he once wrote,

so I didn’t graduate from Brooklyn Tech and ended up at the City-As-School on Carmine Street in the Village. This school was kids who were too smart to sit inside of a classroom and still too dumb not to know they didn’t know shit. You worked a job as an intern during the week and Friday morning you went to a two-hour session to talk about your experience and had the rest of the day to yourself. I was into stealing cars by this time, and I actually would drive a stolen car to the school sometimes. Real talk. I was a dumbass.

Penn never stopped playing the fool, and was so funny and self-effacing it was easy to overlook how smart and pointed he was. ‘As a poor person in America, I still want to contribute to the economy,’ he says in ‘Checkmate’, a vlog about economic instability, check-cashing places and banks. ‘I still want to stay in debt. And I still want to enjoy things … One thing I’ve learned about being in debt? If I die today, I win.’

Penn vlogged and blogged about urban planning, too, and nutrition, the military – all the ways capital sloshed around the neighbourhoods he highlighted and knew. But he also liked to talk about Timberlands – ‘The Boot God’ was one of his many handles. The Decepticons loved Ralph Lauren – the Lo-Lifes, another ‘youth collective’ Penn had been involved with, took their name from Lauren’s Polo brand – and, more often than not, Penn was decked out in Ralph Lauren. (Friends and followers still remember ‘Pologate’, the day he leaked a 65 per cent employee discount code and caused an online stampede.) Among other things, he was a semiotician of streetwear.

But for all the times he went viral, Penn never really cashed in. He mostly worked in construction, volunteering at Ground Zero in the wake of 9/11. Tens of thousands of people who did the same went on to develop cancer of one sort or another, and, a few weeks ago, Penn registered for the CDC’s World Trade Center Health Program. This would have covered some of his medical expenses but by then it was too late. He died last week, at the age of 53.