One of my favorites (though "traditional" in style only) is "Abe Carman" aka "The Robber's Song", from Peter Bellamy's folk opera The Transports. He wrote two quite different versions, both of which are terrific. The second version can be heard on the compilation "Wake the Vaulted Echoes"--don't know if it was also included in the 25th anniversary edition of Transports.

Also search on "goodnight ballads" (such as Tyne of Harrow), which were written by highwaymen. Also songs about Ned Kelly's band, such as "Streets of Forbes".

For poaching, there's "Dogs and Ferrets"/"While Gamekeepers Lie Sleeping" and "The Lincolnshire Poacher".

I assume this topic should not embrace piracy or robbing a woman's maidenhead, both of which would deserve chapters unto themselves. ;-}