‘Doom Mexico’ he was calling it by the end, but when he first came here, Jack Kerouac was enthralled. William Burroughs had skipped bail and settled in Mexico City the previous year, and Kerouac and Neal Cassady drove down to stay with him, their journey across ‘the magic land’ breathlessly recounted in On The Road. Both Burroughs and Kerouac saw Mexico as a blank canvas, a naïve cultural wilderness on which to project their orientalist fantasies. According to Burroughs, Mexico is “basically an oriental culture… where everyone has mastered the art of minding his own business”; Kerouac was less cynical, although no less naïve, in 1952 writing Allen Ginsberg that “the Mexican is great, straight, simple and perfect”.

Kerouac and Cassady stayed with the Burroughses at 37, Cerrada de Medellín (today José Alvarado), a residential street in La Roma, the neighborhood at the heart of contemporary Mexico City’s scenester scene (Kerouac’s poem Cerrada de Medellin Blues was written there). Then, towards the middle of 1951, Burroughs moved round the corner to an apartment in the block at 210-215, calle Orizaba, and it was here that he accidentally-on-purpose shot and killed his wife, cementing his reputation as one of literature’s great misogynists.

After the death of Joan Burroughs, inevitably, the Beat Generation’s love affair with Mexico turned sour. Burroughs remained trapped in Mexico City, checking in every Monday morning with the authorities, and eight months after the shooting Kerouac returned to stay with him. Both were short of cash and patience. Burroughs in particular was suffocating in Mexico, and he had the serious addict’s disdain for Kerouac’s marijuana habit. They fought, and when Kerouac returned once again to the city in December of that year, he rented a small, abode-walled room on the flat rooftop of Burroughs’ building.

Mexico City’s flat rooftops were a space of experimentation and liberty.

‘I took a little dobe block up on Bill’s roof, 2 rooms, lots of sun and old Indian women doing the wash… perfect place to write, blast, think, fresh air, sun, moon, stars, the Roof of the City.’ The rooftop itself was made of thick glass, so when it rained it got slippery. Kids from the building played too close to the edge and it made him nervous. No electricity, of course: ‘Candlelight in a lonely room, and writing about the world’, he intones in Desolation Angels, parts of which he wrote during this episode, as well as the entirety of Mexico City Blues, his most celebrated collection of poems.

The rooftop on which Kerouac lived when he wrote Mexico City Blues is a central presence within and behind the collection. It represented an urban hermitage, an artificial paradise, a retreat backwards in time (he refers to it as both a hovel and a cell, in his Mexican novel Tristessa referencing ‘the Blakean adobe rooftops’). In this, Kerouac all unconsciously pertained to a distinguished literary tradition of Mexico City: el cuarto de azotea.

As with the French chambre de bonne or the English garret, the cuarto de azotea was the room where the maid or porter lived. After the Revolution, however, this dynamic had shifted, and, like the chambres de bonne, the cuartos de azotea acquired a bohemian air. Novelist Valeria Luiselli has documented how, for writers and artists early last century, the city’s flat rooftops were a space of experimentation and liberty, where they were able to construct “a kind of modernist utopia in which gender restrictions were challenged, sexual norms transgressed, moral codes broken, aesthetic principles overturned, and intellectual affiliations reinvented”. Alfonso Reyes lived and worked on an azotea on Avenida Isabel la Católica in 1908, while in the 1920s a range of distinguished intellectuals partook of azotea life: Tina Modotti and Edward Weston, the painters Dr. Atl and Joaquín Clausell, and the poets Xavier Villaurrutia and Salvador Novo, huge names in the history of Mexican literature.

The rooftops were to remain a haunt of artists – in Tristessa Kerouac tells how he ‘sketched a little bearded Mexican artist in his roof hut…We drank tequila in the morning and drew each other—of me he drew a kind of tourist sketch showing how young and handsome and American I am’. But things changed fast as the century progressed. As Carlos Fuentes put it, “Mexico City found in the late ’40s and ’50s its baroque essence, a breaking down of barriers, an overflow”. The figures are dizzying: in the ’20s, the city’s population was about 600,000, while by 1950 it was 3.2 million.

Cultural theorist Carlos Monsiváis describes how this massive immigration from the countryside turned the azoteas of Mexico City into a continuation of rural life: “chickens and goats, shouts aimed at the helicopters because they scare the cows and the laborers milking them, clothes hung out to dry like ripe corn…” The tiny rooftop rooms, Monsiváis continues, accommodate families which reproduce and reproduce as children and grandchildren come and go and family members install themselves for a few months, and the cuarto grows until it contains the entire village from which the first inhabitant emigrated – the cuarto de azotea as a symbol of how life teems in a finite space, a microcosm of the city.

In the decades following Kerouac’s various sojourns, the dynamic of the azotea changed again. In his essay ‘Avenida Álvaro Obregon’, journalist José Joaquín Blanco deplored the decline of La Roma from a decorous, ‘aristocratic’ neighborhood to a run-down, bohemian district. He described how the masonry of the rooftops had cracked and the broken-windowed cuartos been sub-let to ‘solteros pobres, estudiantes y prostitutas’—poor, single men, students and prostitutes—and, to top it all, how the rooftops had been crowned with monumental advertisements, ‘a todo color’, of women in bikinis.

Both Burroughs and Kerouac saw Mexico as a blank canvas, a naïve cultural wilderness on which to project their orientalist fantasies.

Twenty years after Kerouac and Burroughs did, Roberto Bolaño and his cronies ­­- ‘solteros pobres, estudiantes y prostitutas’, all – swarmed in the streets of la Roma and downtown Mexico City. The narrator of his Amuleto rents a cuarto de azotea on calle Tabasco, and in The Savage Detectives, Juan García Madero describes a visit to the set of rooms the poet Pancho Rodriguez shares with his mother and brothers on a calle Tepeji rooftop, amid ‘a vibrant profusion of flowerpots and flowers’. Ulises Lima also lived in a cuarto de azotea, on calle Anáhuac, in Roma Sur: there are books everywhere, García Madero notes, and a miniscule table occupied in its entirety by a typewriter.

Kerouac’s ‘little dobe block’ was an important symbol for the young Roberto Bolaño. In a notebook from the late ’70s, when he still lived in the city, Bolaño noted that ‘[I]n 1955, in a cuarto de azotea of Mexico City… Kerouac wrote the majority of the more than two hundred poems that make up Mexico City Blues. I wasn’t even two at this point.’ He even translated some. In the same notebook, Bolaño admires, autobiographically, the way that Kerouac, another foreigner, ‘opens his body and his movement to the tender bewitchment of Mexico City, and suddenly it is the city (that Mexican madness) which starts to circulate inside him’.

The Catalan critic Josep Massot has argued that Roberto Bolaño’s own literary movement, Infrarealism, constituted a homage to the Beat Generation. He is right when he says that Bolaño’s success in the States is partly due to the fact that his publishers sold him as a Latin American Jack Kerouac. But Massot’s argument that Bolaño was Kerouac’s disciple is based on a few generic similarities, inevitable correspondences of taste and lifestyle. In fact, Bolaño saw Kerouac as a near-contemporary, a fellow-traveller, certainly not worthy of the intense devotion he reserved for the true godfathers, for Borges and the French.

But more than overlaps of style or perspective, what connects Kerouac and Bolaño is their experience of Mexico City. At different points they both sat in their cuartos de azotea, only a few blocks apart the one from the other, hunched over very similar-looking typewriters, smoking very similar strains of weed. And at one point both of them upped and left the city they mythologized, never to return; but that is another story.