Reggae, reggae, and reggae. Reggae (especially white boy american reggae) is by far the most quasi-libertarian music genre you’ll ever find. Jamaican reggae is often weird and anti-capitalist. But here in the states, reggae is extremely anti-big brother, occasionally anti-capitalist (but can be interpreted as state-capitalism and corporatism), but thats rare. When the songs are politically-motivated, they usually deal with subjects of being anti-war, anti-drug war, anti-tax, pro-independence, and pro-freedom and liberty for all, etc…
Here are some of my favorite Reggae bands
Arden Park Roots, B foundation, Ballyhoo!, Can’t Hang, Cipes and the People, Close Enough, Daniel Wesley, Dirty Heads, Dispatch, Doug Means Project, Echo Movement, Freeflow, G. Love, Indofin, Live@subs, Long Beach Dub Allstars, Long Beach Short Bus, Mike Pinto, OPM, P-Nuckle, Passafire, Pepper, Ribsy’s Nickel, Roots of Creation, Scotty Don’t, Starving Millionaires, State Radio, Sublime, Three legged Fox, Tomorrows Bad Seeds, Trolls Cottage, 3rd Alley, and 311. (Some are more or less politically-motivated, and some are more or less libertarian.)