Vagabond Buddies

"Well, that's another nice mess you've gotten me into!"

Two funny guys who travel around the world (often in the Hollywood Atlas version), and though often at odds with each other are ultimately inseparable. They take on various odd jobs, Short Cons and capers, often to pay off their debts. They can go flat broke even quicker.

They often will have to compete for the affections of one local girl who assists them in their escapades.

Examples of Vagabond Buddies include:

Anime and Manga

Ran and Meow from Kazemakase Tsukikage Ran are female versions of this.

Film

The Road To movies with Bob Hope and Bing Crosby (and Dorothy Lamour as the love interest) are the Trope Codifier.
The Laurel and Hardy films.
Though they were actually brothers, Garth and Hub were this in their younger days in Secondhand Lions.

Literature

George and Lenny from Of Mice and Men.
Flaubert gave us Bouvard et Pécuchet who are more or less this.

Live Action TV

Troy and Abed from Community
Sam and Dean from Supernatural

Theatre

"Con" Kidder and "Kid" Conner in The Red Mill.
Vladimir and Estragon in Waiting for Godot.

Web Comics

Griffen and Molly from the webcomic Dicebox are a prime example of this trope.

Western Animation

Naturally, given that it's styled after the Road To movies listed above, The Road to El Dorado had Miguel and Tulio.
George and Junior from Tex Avery's MGM shorts are this, though with a lot more animosity, chiefly from George to Junior.