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Picaresque

Picaresque is a genre of usually satiric prose fiction originating in Spain and depicting in realistic, often humorous detail the adventures of a roguish hero of low social degree living by his or her wits in a corrupt society.

A traditional picaresque is often a Shaggy Dog Story and/or has a Random Events Plot. Elements of the picaresque frequently show up in Cyberpunk stories.

Examples:

Film

All of the Dollars Trilogy, especially The Good, the Bad and the Ugly.

Literature

El Lazarillo de Tormes is generally considered the first of this genre.
Don Quixote has some elements of this genre.
The Adventures of Huckleberry Finn
Moll Flanders
Candide
A Confederacy of Dunces
The Dying Earth series by Jack Vance
Book of the New Sun by Gene Wolfe
The Gentleman Bastard series
Simplicius Simplicissimus (the English title of Der Abenteuerliche Simplicissimus), one of the earliest true novels in the German language.
The Unfortunate Traveller: or, the Life of Jack Wilton (1594) by Thomas Nashe.
Cloud Atlas: Somni describes 'The Ghastly Ordeal of Timothy Cavendish' as such.
Life of Pi
Middlesex
Baudolino
The Satyricon

Music

The Code Geass OST song Picaresque (which could double as an ImageSong for Lelouch) is probably named for this genre, considering the kind of world that Lelouch lives in, and his own way of fighting it.
The The Decemberists' album Picaresque.

Theatre

Mother Courage and Her Children by Bertolt Brecht, set in the Thirty Years' War with various allusions to Simplicissimus.

Web Original

The Lay of Paul Twister mixes elements of this genre in with High Fantasy and Trapped in Another World.

Western Animation

The Simpsons has many elements of the picaresque genre: Both Homer and Bart are notorious underperformers who avoid hard work and shirk their duties whenever possible, are generally irresponsible, treat their fellow men shabbily and take refuge to lies when it suits them, all the while being not especially bright. Yet they somehow always manage to avoid all serious consequences of their foolishness or egoism and are likable characters despite their many flaws.