The plan is to leave Chicago by 7:30 or 8am but the car’s late. It’s not delivered till almost 9 so I’m behind before starting out. I’m annoyed but figure to get to the motel in New Jersey by 10 or 11pm rather than 8 or 9. No big deal.

I queue up Sarah Weinman’s Scoundrel and start east. I listen to her wild story about William F. Buckley and the deathrow psychopath who hoodwinked Buckley into financing the year’s long court and publicity battle that sprang him from jail. I think back to that one night I slept on Weinman’s couch during a book-tour stop in New York City. It’s not a great surprise she’s devoted her literary career to researching criminality and mental illness considering her home situation back then. It’s good to know she was able to rise above it and make a success, albeit due to very dark material. Her book keeps me company through Indiana and Ohio and into Pennsylvania.

The rain and sleet start somewhere around Youngstown and keep a steady clip as I roll past the 18-wheelers. I stop for dinner around 5pm at some truck stop that loudly advertises the world’s worst apple pie. Soon after getting back on the road traffic is at a standstill. At the highest elevation on I-80—about ten miles ahead—several trucks have smashed up on the ice. We barely move the next three hours.

As I sit there listening about Edgar Smith’s last days—he died in another prison for trying to kill a different woman, long forgotten by the country’s foremost conservative and his lackeys—I think back to the first time I was stuck on this road this way. It was the winter of 1994 and I was driving my white ’72 Skylark with a U-Haul hitch attached back to Boston after quitting grad school in Indiana. I’d planned to do the drive in one go but had to check into a motel after traffic started moving again. I’d cursed that road then, vowing never to travel it again, just as I curse it now 28 years later.

But from Chicago to New York City, I-80 is a straight shot and hard to avoid. I think about stopping at some other motel, then driving the extra few hours in the morning but just keep going.

I pull into the Quality Inn lot in Ledgewood just after 2am.

I park on 44th Street a block east of the theater, then walk south to the Whitney. It’s sunny, in the 50s, and the city looks good. I note like I do every time I come hear how oblivious New Yorkers are to anyone and anything on the sidewalk other than themselves and their own route. It’s like they willfully pretend no one else is there, just obstacles in their path. I laugh while doing my best to get out of their way.

The Edward Hopper show is spectacular. The New York he painted is the iconic city of myth, memory, and American culture. The current iteration feels like an overbuilt theme park in comparison. But the sideways light creeping past rows of city blocks in his canvases is still there as I walk back north. I text John for dinner recommendations in the theater district and he points me toward Jimmy’s Corner. There’s no food there but Beam on the rocks is $4 a go. I’d paid more for coffee earlier in the day. Drinking there makes me feel like I’m in a New York from long ago.

The timewarp feel is enhanced by the bartender’s voice. It’s a dead ringer for Nicky, who died from hard living almost a decade ago. My current apartment is downstairs from the last place Nicky lived.

People filter in from the afternoon show across the street. The guy who sits down in the barstool says I’m in for a treat. it’s his second time seeing the show. He’s retired and flies into the city a couple times a year just to see the shows. We talk about Ralph Fiennes as Robert Moses and he tells me tickets are going for 5K on Stubhub. He loves theater but not that much.

I’m excited to see Bunk from The Wire play Willy Loman but it’s Sharon D. Clarke who steals the show as Linda. Everything she says is like a knife in the heart. Then Willy’s eulogy with the capper about his having the wrong dreams. It’s like an epitaph for this whole country.

I put on Jimmy Giuffre’s Western Suite and drive to Boston.

—Listen to my talk with Mallory Smart, then tune back in Wednesday for one with John Hodgman.