Too easy. Especially if you dive into the Folk tradition: not only are there many songs based on historical events, but many were actually written at the time so are even better.

For example, one of my favourite artists at the moment is the Australian "Bush" band the Bushwackers. Their album "Faces in the Street" includes two fantastic songs about the 1891 Shearer's Strikes: "The Ballad of 1891" a unionist piece from the 1950s and Henry Lawson's poem (set to music) "Freedom on the Wallaby" which is contemporary with the events. Not to mention the title track, another one of Lawson's fantastic verses urging for a communist revolution. Fortunately somebody has actually uploaded this one to youtube: a lot of the band's material is out of print and can be hard to track down (legally or not).

Woody Guthrie, Pete Seeger, Phil Ochs, Redgum (another great Aussie act), The Weavers, Almanac Singers, U. Utah Phillips, Tom Paxton, Cisco Houston... hell just take a quick look through Folkways Records back catalogue and take your pick. All great stuff.

If you're looking to do that, make sure you also include an examination of any bias the piece may have. For example, Johnny Cope does give the outline of what happened at Prestonpans and could be a good jumping-off point, but it's also basically a piece of character assassination against the titular general, making charges he was cleared of under court martial. The Haughs of Cromdale is another good example of this, where the first half (approximately) is pretty accurate, and then followed by essentially wishful thinking (when the Jacobites come back and win it).

Off the top of my head, other songs include Sink the Bismark by Johnny Horton, The Battle of Otterbourne/Lammas Tide which is Child Ballad 161 goes into dull detail about the battle and is now usually shortened. If you want more, I've likely got some, but won't be able to look them up until later today.