A gaucho was a roaming cowboy of the Argentine and Uruguayan pampas (the vast grasslands of South America) during the 18th and 19th centuries. More than any other Spanish figure, the gaucho is a symbol of romanticism because of their free and natural lifestyle. They have a strong cultural identity and used to be common figures in Spanish literature due to their exciting, but ultimately tragic, history. Gaucho history, unfortunately, is being forgotten more every year.
The Gaucho is one of the last true figures of anti-establishment in American history. They opposed the rapid settlement and industrialization that was so common during their time period. The solitude of the outdoors was a necessity, as living free to them meant living in the plains. Because of their inherent need for freedom, Gauchos made a living by breeding cattle. They would take their cattle herds, which were normally about 20 cattle large, and wander the pampas freely, since most South American land was not inhabited at the time.
One could easily distinguish a guacho because of the way he dressed. They would constantly wear their large sombreros, which they would often ever wear to sleep. Over their shoulders they would wear heavy ponchos, made out of wool or similar fabrics. The gauchos were a people of few possessions. However, every gaucho carried three essential items: his water bottle, guitar, and knife. The water bottle, obviously, was in order to live. The guitar was a gaucho's most prized possession. Because of their extreme shyness, the gaucho's only companions were the cattle and his guitar, which he wore slung over his back. Although they rarely played in towns, many poems and songs have been written about the beauty and emotion with which a gaucho would play his guitar.
Knives were also an essential item. Although normally reticent and reserved, gauchos were known to get into fights constantly. Foolish farmers, drunken barflies, and other gauchos would all often provoke a gaucho into brawls. Unless it was a gaucho versus gaucho match, the fights were over soon; no one in South American was more skilled in the art of combat than a hardened gaucho. The mirror matches, however, were intense. In order to challenge a person to a fight, a guacho would throw his poncho over his head and wrap it around his arm. The thick poncho served as a shield. With their knives out (knives were the accepted weapon of duels) the combatants would circle each other, going in periodically for quick swipes. If both opponents were skilled, the fight could easily last for an hour. Many ears, fingers, and noses were lost as a result of these battles.
During the tumultuous times of the early 1800's, gauchos became an oppressed people. With the government leaders changing almost annually, they began to be forced into military service for the next dictator. The most notable instance of gaucho military influence was during the overthrow of Juan Martín de Pueyrredón. The caudillos, ambitious landowners that sought to take control of South American states, were the guiltiest of oppression. The restriction of military service was often too much for the gauchos, who would sometimes become depressed and serve as an easy target during battle. Gauchos who refused to fight were promptly shot, often going out playing their beloved guitars.
Guachos began to disappear around the 1850's, when South American governments started selling cheap land to Europeans. This influx of people, along with the development of better technology, soon picked away at the lifestyle of the gaucho. In a very short period of time, the pampas disappeared, leaving no room for free roaming or grazing. Rather than conforming to the idea of owning land, most let the lifestyle die. The last guachos were often seen leaning against building sides with their sombreros pulled over their faces, waiting for nothing. By 1900, the guacho was extinct.
In 1872, Argentine Jose Hernandez wrote the remarkable epic poem Martin Fierro, which is now regarded as the best piece of guacho literature ever written and one of greatest Spanish poems. It is dramatic, glorious, and, in the end, heartbreaking. Don Segundo Sombra, written in 1926 by Argentine Ricardo Guiraldes, is the quintessential gaucho novel. These pieces of literature, although not as well known to in English as others like Don Quixote, are both remarkable and well worth reading. Also notable is the 1927 silent movie The Gaucho, starring Douglas Fairbanks.
Sources:
Senora Barrera, my Spanish teacher
www.tangolibre.com
Also, if there's enough interest, I may work on translating the entire poem of Martin Fierro since I don't believe there are any English translations of it online. I could also just be lazy, but if you are interested in the subject, let me know. | 
