1.

Reading Jack Kerouac’s On the Road, you get used to sudden changes in geography. Always convinced that the real party is in full swing elsewhere, Sal Paradise and Dean Moriarty are continually hopping in the car, exclaiming “Yes!” and “Phew!” as they tear off to another city, another coast. Of course, the sadness of On the Road — published in 1957, as the booming interstate highway system was beginning to pump homogeneity through its capillaries — is the characters’ slow realization that things fall apart in one place as well as another, and by the novel’s halfway point, Dean’s urgings to head to the next city inspire a certain weariness in the reader. But there’s one move that makes the reader sit up, for it signals a shift not so much in the novel’s location as in its metaphysics. It’s announced, with no warning, by the minor character Stan Shephard, who poses an innocuous question less than a hundred pages from the novel’s end: “Is it true you’re going to Mexico?”

It is true, and if this is a natural turn for Kerouac’s restless protagonists to take, it also signals that On the Road, which Louis Menand says “made America a subject for literary fiction,” is turning its back on the big, sad nation that is its raison d’être. It’s an uneasy proposition, one that leaves the reader stricken with the sort of helpless nausea felt at the crest of a roller coaster’s hump. Of course, excitement is mixed in there, too. Even if you know little more about Mexico than the drug violence and immigration debates that define it in American news cycles, its name alone connotes some promise of exotic adventure, Montezuma’s gold and so forth. And if you have an ounce of sympathy for Sal and Dean, after so much dreary wandering, you want to believe Dean when he cries, “Man, this will finally take us to IT!”, even though you know it will not. As Sal says, there’s just something different about driving to Mexico: “It was no longer east-west but magic south.”

Two other major American works of this period concurred in this assessment of Mexico’s appeal: Saul Bellow’s The Adventures of Augie March (1953) and Truman Capote’s In Cold Blood (1966). Though vastly different, these three books — the urtext of the Beat Generation, the great American picaresque, and the definitive modern True Crime account — all contain characters that believe Mexico will cure their American disease. Sal and Dean; Augie March and his lover Thea Fenchel; the murderers Dick Hickock and Perry Smith — at one point or another, they all locate the American Dream south of the border. And with each duo’s decision to leave the U.S. for Mexico, the queasiness provoked by Stan Shephard’s question arises once again. Why is this? Why don’t the Paris leanings of the Lost Generation or Pynchon’s demented spins of the globe provoke a similar response? The answer has to do with these books’ portrayals of Mexico as the last, best hope for a renewed frontier; their failure to find it marks the end of the end of American writers’ romance with the West.

2.

When Frederick Jackson Turner declared the closing of the frontier in 1893, he made no mention of Mexico, and why would he? Americans have always been less than precise in articulating Mexico’s role in their nation’s Westward Expansion. Mexico ceded an astounding half of its territory to the States in the Treaty of Guadalupe Hidalgo, which ended the Mexican-American War in 1848. Dictating terms that followed predictably from the expansionist rapacity that prompted the conflict, the United States acquired California, Nevada, and Utah — as well as most of New Mexico and Arizona and parts of Colorado and Wyoming. Even after this grab, Americans continued to take advantage of a border even more porous than today’s leaky boundary, treating Mexico as America’s exotic backyard. “The Border” came to signify less a delineation than a land where the United States shaded into Mexico, an effect seen in the lazy deployment of the term “Western,” used to describe tales that often take place to the south, in Mexico or in territory formerly belonging to it — the Alamo, Rio Bravo, and The Searchers, to name just a few.

The Mexican territories that became American states were much faster to develop than the country they once belonged to, and so to the adventurous American mind of the twentieth century, Mexico appeared as a land of contiguous exoticism, both different from America and under its thumb. In The New Yorker in 1979, the great Mexican writer Octavio Paz observed: “In general, Americans have not looked for Mexico in Mexico; they have looked for their obsessions, enthusiasms, phobias, hopes, interests — and these are what they have found.” In one sense, Paz is mistaking an American attitude towards the world in general for an American attitude toward Mexico in particular. But it is true that Americans in Mexico feel a sense of ownership not possible in Europe thanks to distance, an entrenched and “civilized” culture, and a mostly white population.

Paz’s dictum certainly applies to the characters drawn by Kerouac, Bellow, and Capote. They constantly mistake myths for truths, projecting a blend of primitive fetishizing and general touristic ignorance onto their surroundings and calling the result Mexico. Thus it is that Sal can place himself above “the Pedros and Panchos of silly civilized American lore,” despite having just presented us with a grinning border official who is that stereotype incarnate: “Welcome Mehico,” he says. “Have good time. … Everything fine. Is not hard enjoin yourself in Mehico.” The same goes for Augie March, who travels to Mexico with his new lover, Thea Fenchel, to train an eagle to hunt. Augie blithely attributes the locals’ enthusiasm for the bird (Thea thinks her endeavor will make for some lucrative National Geographic articles) to “the ancient respect” the bird enjoys “from the old religion and the great class of knights in those days of obsidian sword slaughter that Díaz del Castillo witnessed.” Augie may be better read than Sal and Dean, but he’s hardly better informed.

Where do these ideas come from? As with many twentieth-century American misconceptions, a large share of blame can be yoked to Hollywood. Consider Capote’s description of a Phillips 66 map that the dreamy Perry Smith reads in a diner:

Ink-circled names populated the map. Cozumel, an island off the coast of Yucatan, where, so (Perry) had read in a men’s magazine, you could “shed your clothes, put on a relaxed grin, live like a Rajah, and have all the women you want for $50-a-month!” … Acapulco connoted deep-sea fishing, casinos, anxious rich women; and Sierra Madre meant gold, meant Treasure of the Sierra Madre, a movie he had seen eight times.

Perry Smith was hardly the only American in those years whose image of Mexico was intertwined with Humphrey Bogart; while driving south, Dean invokes “those enormous Sierra Madre mountains we saw in the movies.”

This stuff was in the air. In the 1950s, a group of American film stars that included John Wayne, Cary Grant, and Errol Flynn bought the Hotel Los Flamingos in Acapulco, ushering in an era when Mexico changed from an exciting land of “diseases, robbery, and the dangerous population” (Augie’s words) into an exciting land of marketable adventure and saleable exoticism. “Just say the words and we’ll beat the birds/Down to Acapulco Bay,” sang Frank Sinatra, who began frequenting the resort with the Rat Pack. In the years to come, Acapulco played host to Howard Hughes’ last days, Liz Taylor’s third wedding, and JFK and Jackie’s honeymoon. “I didn’t realize right away how many visitors from the cool and cold were paying their good dough to be here,” says Augie March.

The movies and tabloids lent commercial legitimacy and glamorous appeal to the entitlement and avarice that hadn’t changed since the days of Jimmy Polk. Even if you couldn’t afford to join the party, you could still find a good time in your own price range (like Sal and Dean, who run up a thirty-six dollar tab in a whorehouse) or plan to strike it rich quick like Dick and Perry, whose moneymaking schemes include diving for sunken treasure, deep-sea fishing, and chauffeuring stolen cars. For a time, it works. “This is finally it. The way it ought to be,” sighs Perry, fishing from a boat hired by a wealthy German who takes the fugitives into his patronage.

“Still,” Capote writes, in the language that wields the ethically dubious power of inspiring sympathy for two killers, “he knew that it couldn’t continue — that it was, in fact, destined to stop that very day.”

3.

“For a moment, at the frontier, the bonds of custom are broken and unrestraint is triumphant,” wrote Frederick Jackson Turner in his Frontier Thesis. In other words, a frontier’s time as a frontier is limited. What these characters think they seek in Mexico is what the theologian Belden Lane in his book Landscapes of the Sacred calls chora (borrowing Plato’s term for “space”) meaning a place of unique power, often of a spiritual character. But, as Paz said, Americans don’t really look for Mexico in Mexico — they look for a more perfect America, at once free of materialism and more conducive to it. This is an untenable quest, and soon, by engaging in the same mad dash for money and luxury as they did in the U.S., Mexico becomes to these characters what Lane calls topos, a space like any other, just a spot on the map. Boredom and disappointment ensue.

4.

“It was one fiesta after another meantime,” says Augie March:

The band plunged in the zócalo, clashed, drummed, and brayed; the fireworks bristled and ran off in strings, the processions swayed around with images. A woman died of a heart attack at a five-day drunk party, and there were scandals. Two young men, lovers, had an argument about a dog and one of them took an overdose of sleeping pills.

In this impassive retelling, you can detect the weariness of settlement, novelty passing from this latter-day frontier like heat from a corpse. At one point, Augie tellingly describes the writers, financiers, and layabouts he encounters in Mexico as “the American colony.” The myths that these Americans sought in Mexico — Augie’s obsidian sword slaughter and Perry’s buried treasure and Sal’s “great, grave Indians” — have been crowded out by the single great truth of gain. “I saw anew how great a subject money is in itself,” Augie says, reconsidering his reasons for coming south.

It’s money that drives Dick and Perry north, back into the jurisdiction of the laws that will ultimately put them to death; they simply run out of it. It’s Augie’s eager libido that destroys the armature of his stay in Mexico, his relationship with Thea, which comes crumbling down with excruciating inevitability. Augie hangs around Mexico, and sees the exiled Trotsky. (In his younger years, Bellow traveled to Mexico specifically to meet Trotsky. His timing was spectacularly bad, arriving the day after an assassin sank an ice pick into Trotsky’s skull.) Augie perpetrates the most vividly-described breakup bender in any novel, before nonchalantly returning home: “Anyhow, I felt now that there was something about the effect of Mexico on me, that I couldn’t hold my own against it any more and had better get back to the States.” This dissembling is typical of Augie; it’s his own desires that are having an effect on him, of course. Mexico represents the buoyant Augie’s lowest point. Though he recovers much more nicely than Sal and Dean or Dick and Perry, it’s no accident that Bellow situates his convalescence in Chicago, the beating heart of Augie’s America; only there can he reorder his priorities and resume his quest for a metaphysical frontier.

And what of Sal and Dean, the wayward pair with whom we began? Their appetites get the better of them, too, as Sal fulfills Emerson’s grim prediction that “Mexico will poison us”: “Then I got fever and became delirious and unconscious. Dysentery.” The restless Dean leaves Sal while he’s laid up, back to New York for (what else?) a woman. “All that again?” asks a crestfallen Sal. “All that again, good buddy,” says Dean.

In these ragged retreats from Mexico lies the fullest answer to the question of why Stan Shephard’s question is so unnerving even before any borders are crossed. These Mexican ventures inspire both fear and hope — the fear of discovering that America is both Death Valley and Gopher Prairie, simultaneously too large and not large enough for our insisting dreams, and the hope that there are more frontiers to discover. Their departures both surrender and reaffirm the American promise that we all want to believe in, even as we deny it; their empty-handed returns only confirm the folly of keeping the faith. In these sad dispatches from Mexico, Kerouac, Bellow, and Capote anticipated the post-Vietnam pessimism about Mexico that artists like Sergio Leone and Cormac McCarthy would make de rigueur. They were the first to spot the evening redness in the south.

Image: Cam Villay/Flickr