I like a lot of folk music, so Woody Guthrie, Utah Phillips, Phil Ochs, David Rovics and Sarah Ogen Dunning. Old folk music was the most lefty American genre. Leadbelly had a lot of left wing songs too, I understand he was skeptical of white socialists but he was very popular among the movement. He's also like one of the greatest musicians of all time. Oh and if you've never listened to Victor Jara, absolutely just stop what you're doing.
A little more country, but John Prine is absolutely essential listening, unrivaled in the songwriting category. Kris Kristofferson was a lefty, and for a more modern take, Sturgill Simpson is a really unique artist with good social messages. Earl Scruggs also has a lot of pro union/pro worker/pro working class songs, and is one of the greatest living country/Americana musicians.
Gang of Four is really good and underrated, one of my all time favorites. I used to.really think the clash were lefty, and they certainly had left/anarcho sympathies, but Joe Strummer almost always wrote a final cringe verse into his political songs, like Washington Bullets. I'll always dig his sympathy for homeless and outlaws, but geopolitics he was kinda moderate. Over time I've come to appreciate Mick Jones's poppier less political stuff. But Gang of Four never drops the ball, and I've come to favorite their first two records, Entertainment and Solid Gold. While we are listening to punk music, I'd throw in The Minutemen as honorable mentions. Less explicitly left-wing political, but D. Boon was such a prolific and intensely thoughtful writer, that I think he was a comrade.
Another super underrated pick is The Refused, the Shape of Punk to Come. This record is undeniably a work of situationist Marxist theory, this is my favorite pick of the bunch. Napalm Death is another heavy selection, many of their songs are about solidarity and anti imperialism.