Over the past several years, the New York-based artist Drake Carr has gained a steady following for his live portrait sessions, which have been staged at galleries in New York City, Los Angeles, and Paris, and even in people’s homes. A keen observer with a love of fashion illustration, Carr renders his sitters – be they strangers or cultural luminaries such as model Pat Cleveland or actress Hari Nef – with the delicate precision of a lapidarist.

‘Doing these walk-in shows for the past 3 years has been like a boot camp,’ Carr, 33, tells me this summer when I visit his Brooklyn studio. Each session is an endurance test, a sort of psychological fast draw where Carr works quickly to distill both the physical characteristics and emotional undertones of his subjects.

This fall, he brings the same thoughtful spirit to a much longer-simmering body of work: a series of 10 painted wooden cutouts that Mariposa will show in its booth at Art Basel Paris. The project has been 2 years in the making – a pace that has allowed Carr, a self-taught artist who once cranked out 150 drawings over the course of a 2-week residency, to go deeper. ‘You just don’t usually get that amount of time,’ he says.

Each cutout begins as a piece of sanded maple plywood, just an inch or so thick, procured from the hardware store and cut with a jigsaw. Onto the wood he paints his rakish characters, each an amalgamation of people he knows or has observed in public, clippings from magazines, and himself. They are colorful and glamorous, with snatched waists and rippling quads, often posing as if they are in the middle of a dance move. They have the same fashion-illustration DNA as the live drawings, straddling the line between campy and chic, but here they are supersized and painted in such fine detail that you half expect them to leap off the wall and start voguing.

But along with the glamour, Carr has given them an air of mystery. Take the figure wearing a long navy coat with elegantly gloved hands, his hip cocked in one direction as he glances in the other. ‘He’s kind of like a heightened version of me,’ Carr says. ‘He’s not looking at you, but he is looking at someone, and he is aware that he’s being looked at.’

The dichotomy of being both the watcher and the watched is a common thread in Carr’s work – a byproduct, perhaps, of his time working in nightlife. Carr spent many years bartending at a tiki-themed gay bar in Bushwick called Happyfun Hideaway, which also served as his de facto gallery. His large drawings of people, which were stapled to the bar’s walls, are the precursors to the wooden cutouts that Mariposa will present at Art Basel. From Carr’s perch behind the register, he would see the way people oscillated between losing themselves in whatever it was they came there to do – dance, flirt, drink, let go – and the self-consciousness of both looking around and being seen. The cutouts capture that tension, particularly the plaid-shirted hunk whose face is caught between looking left and straight ahead.

The razzle-dazzle of the 1980s is often evoked when discussing Carr’s work, and indeed that era’s movies, books, and especially its music are touchpoints for the artist. You see it in the garments these cutouts wear – a blond woman’s windbreaker or the strong shoulders of a navy coat, à la Grace Jones on the cover of her iconic 1981 album Nightclubbing.

‘I am drawn to that era for a lot of reasons,’ Carr says. ‘It seems like an amazing time, but also part of why it was amazing is that it’s underscored by an incredible darkness. And I think those things together make something really poignant.’ It is that mix that people often miss when they bring up the whole 1980s thing. ‘The darkness as an undercurrent is pretty important to me,’ he says.

Carr might not have experienced the 1980s firsthand, but working in nightlife brought plenty of its own shadows. The hours could be long, people would get too drunk or high, bad behavior ensued. It is ‘that moment when the carnival music turns scary,’ Carr says. ‘The bright pink lights and the loud music’ – at first, so fun – ‘suddenly become menacing.’ In his cutouts, that moment is never too far off; something could go wrong at any minute. ‘I think that’s what makes the bright, fun part so good, because it’s so on the edge of being too much.’

But they are unmistakably beautiful, almost effortlessly so. They do not have the same hallmarks of the artist’s hand as his drawings do, nor do they bear the marks of a carved wood sculpture. One of the goals Carr has for them is that they look like they just…appeared. Carr, who grew up in a Christian household outside of Flint, Michigan, likens it to stained glass in a church. You’re not at church for the art, and you’re not thinking about the labor that went into it, though of course each panel took much time and craft and effort. You almost take the stained glass for granted, like it just…appeared.

‘I’m more inspired by the idea of people getting to experience art in a way that doesn’t feel so sterile or controlled,’ he says. That is why he loves it when his work appears in unexpected places; it becomes less about who made it or what it is for, and more about how people live among it. That has been true of his drawings in bars, the airbrushed T-shirts he has made for friends, the party flyers he illustrated when he first moved to New York from Michigan 11 years ago. And it is true of the cutouts, which are so far from the typical install for an art fair.

I tell Carr that I have been out dancing at Happyfun Hideaway; that I probably was one of those people he would see half-clocking his drawings but mostly moving about the room with the art as a backdrop. ‘I hadn’t realized they were his,’ I say sheepishly.

‘And that’s the thesis of the show,’ he says back, smiling. ‘That you don’t know.’