Esquire October/November 2022

THE ONLY TIME I HELD A HANDGUN WAS AROUND MIDNIGHT ON September 5, 2004. A day earlier, one of my best friends, Brett Harman, had been murdered—shot dead by two brothers in a parking lot alongside another dear friend, Kevin McCann, at a tailgate in North Carolina. There was a disagreement, and the brothers returned armed and killed them. I spent the ensuing twenty-four hours with family and friends. But by Sunday night, I was alone at the bar across the street from my apartment in Chicago, closing it down with the bartender, Leo, a friend and an unofficial counselor to my roommates and me. He let me stay after closing, lights off and music low, for a nightcap. I’d confessed much to Leo over the years, but I didn’t tell…

I WAS STARTLED WHEN THE GUY WHIZZED past me in his matte-black BMW i8. He was gunning it down my street, all but leaving smoldering tire tracks like in Back to the Future and, perhaps most damningly, making the pavement vibrate to the new Drake album. My dander got all the way up, and I shouted it before I had time to think. Not “Hey!” Not “Slow down, asshole!” Not “Hey, this is a residential neighborhood full of kids and dogs and at least one family with a giant tortoise as a pet, but that’s a story for another time—slow down, asshole!” No. What came up from the depths of my soul was one perfect syllable, a single word that I yelled at a volume that startled me yet again and…

WHEN THE DREADLOCKED, FACE-TATTED ARTIST WITH THE RASPY voice and penchant for good-natured trolling broke big in 2017, many wrote Trippie Redd off as another big-talking quick hit in the mercurial world of young rap. Five years later—after a string of top-five albums, armfuls of platinum singles, and collaborations with giants including Drake, Lil Wayne, and his late friends the generational avatars XXXTentacion and Juice WRLD—Redd’s doubters have been silenced. At 23, he is a Gen Z music essential. Now he’s going back to the series that started it all: A Love Letter to You 5 is expected to drop in October. The anticipated final installment in his signature collection is not about one person but is instead “to everyone who opens it and listens,” Redd says, finishing up his first…

IT WAS AS BOXY AS A METAL TOOLBOX, YET INSIDE IT SMELLED LIKE leather and thick carpet. I didn’t know it then as a second grader, but I was experiencing a revolution in America. The SUV as status symbol had arrived in the form of the British-made Range Rover. One of my dad’s closest friends had purchased one when it first became available in the States, in 1987. It reminded me a bit of a Grand Wagoneer but sturdier, posher. Range Rover families still went camping, but you imagined that they cut the crusts off their sandwiches. You could get used to that kind of life. By the early ’90s, the car was a veritable sign of class among fancy folk with good taste. I loved that Griffn Mill, the Hollywood producer…

ESQ: Our political climate is so polarized these days. How do you think about political fiction now? GS: A story is a place where politics takes off its stiff clothing and puts on some pajamas. You suddenly see that politics always shows up in people’s lives. Fiction gives those people room to move around. But this is where the skill comes in, because if it’s just overt propaganda, fiction is very snobby about that. Even if the writer has strong political beliefs, it forces you to personify and particularize them. In that process, I’ve always found my political beliefs not exactly softening, but becoming more intelligent. They’re more empathetic and a little more patient. Reading a story that has an ostensibly political basis does the same thing. ESQ: Does setting up a…

THE SAN FRANCISCO BAY AREA IS THE LAND OF ALLBIRDS sneakers, venture capital, work that feels like play—and a 16thcentury-style inn with leaded windows and a menu featuring liver and onions. Nonlocals would be forgiven for expecting sun and bikinis on a visit to Muir Beach, California, population 304, but meteorologically speaking it’s more like England than Santa Monica. Hence the genius of the Pelican Inn. The tavern is nestled in a foggy valley in the Golden Gate National Recreation Area, just down the road from craggy Muir Beach and a short drive from Muir Woods, with its centuries-old redwood trees. Try this: Explore the forest, hit the beach (fleece required), then retire to the Pelican Inn for a game of darts, a British ale, and a plate of fish-and-chips…