- Written directed by John Sayles.
Joe Kenehan 
- You think this man is the enemy? Huh? This is a worker! Any union keeps this man out ain't a union, it's a goddam club! They got you fightin' white against colored, native against foreign, hollow against hollow, when you know there ain't but two sides in this world - them that work and them that don't. You work, they don't. That's all you got to know about the enemy.
- Fellas, we’re in a hole full of coal gas here. The tiniest spark at the wrong time is going to be the end of us. So we got to pick away at this situation, slow and careful. We got to organize and build support. We got to work together. Together! Till they can’t get their coal out of the ground without us cause we’re a union! Cause we’re the workers damn it and we take care of each other!
Sid Hatfield 
- I take care of my people. You bring 'em trouble, and you're a dead man. Sleep tight, Kenehan.
- I've met Mr. Felts. I wouldn't piss on him if his heart was on fire.
Few Clothes Johnson 
- I've been called nigger, and I can't help that's the way white folks is, but I ain't never been called no scab!
Danny Radnor 
- [Narrating] It were 19 and 20 in the southwest fields and things was tough. The miners was trying to bring the union to West Virginia and the coal operators and their gun thugs was set on keeping them out.
- We done it mama! We're gonna have the union!
- [Narrating] All we got is our misery, Joe Kenehan used to say, and the least we could do is share it.
- 'Round here, there's the Missionary folks. They's the hardshell Baptists. Then there's the Freewill folks, which is your softshell Baptists. Right now, I preach for both.
- Cold Mountain representitive:These picks and shovels are to be considered a loan from the Stone Mountain coal company; their cost will be deducted from your first month’s pay. Tool sharpening, provided by the company, is 25 cents a month. Use of the wash house is 75 cents a month. Medical doctor, provided by the company is 2 dollars a month, special procedures extra. Your train ride here, provided by the company, will be deducted from your first month’s pay. Your pay will be issued as company script, redeemable for all goods and services at the company store. Purchases of any items available at the company store from outside merchants will result in firing without pay… Powder, fuses, lamps, head gear, all appropriate clothing will be available at the company store, and Stone Mountain will generously advance you a month’s supply of these items, payment to be deducted... Rentals will be for one room, 2.50 a month. Company rule, no more than two people in one room, children included. Electricity, where that is feasible, will be one dollar a month...
- Sephus: [Opening lines of film] Shootin' coal! Shootin' coal!
- Hardshell preacher: The Prince of Darkness is upon the land. Now in the Bible his name is Beezlebub, Lord of the Flies. Right now on Earth today his name is Bolshevist! Socialist! Communist! Union man! Lord of untruth, sower of evil seed, enemy of all that is good and pure and this creature walks among us. What are we going to do about it?
- Foothill man 1: This your machine? [Indicates the Model T Ford.] Heard it last night, too. It's an offense to the ear.
- Foothill man 1: You folks try and keep the noise down you'll do fine. Help yourself to the bird and the rabbit. But if you see any hogs, they's probably ours. We'd appreciate it if you leave them be.
- Hill man: Grab his ankles missus, and mind your dress. He's a bleedin' like a stuck pig.
- Mrs. Knightes: T'ain't no guns allowed at t'dinner table!
- Joe Kenehan: When do we get to Matewan?
- Train conductor: You don't want to go there, mister. Ain't nothing but crazy people.
- Griggs: [Asking a foothill man about his rifle] Where'd you get that piece? Spanish War?
- Foothill man 2: Nope. War Between the States.
- C. E. Lively: Who wrote The Iron Heel?
- Joe Kenehan: Jack London.
- Sephus: Where's Joe Hill buried at?
- Joe Kenehan: All over the world. They scattered his ashes.
- C. E. Lively: Which eye is Big Bill Haywood missing?
- Joe Kenehan: His right one.
- C. E. Lively: How'd Frank Little die?
- Joe Kenehan: Butte, Montana ... they hung him from a railroad trestle.
- Older Baldwin-Felts man: Ever hear of the Hatfields and McCoys, son?
- Young Baldwin-Felts man: Heh. Sure I have have.
- Older Baldwin-Felts man: This here Matewan's their stompin' ground. They'll put a bullet in brain just as soon as look at you.
- It takes more than guns to kill a man.
- At the coal company they use you until you wear out.
- Chris Cooper — Joe Kenehan
- James Earl Jones — "Few Clothes" Johnson
- Mary McDonnell — Elma Radnor
- Will Oldham — Danny Radnor
- David Strathairn — Sid Hatfield
- Ken Jenkins — Sephus Purcell
- Gordon Clapp — Griggs
- Kevin Tighe — Hickey
- John Sayles — Hardshell Preacher
- Bob Gunton — C.E. Lively
- Josh Mostel — Cabell Testerman
- Nancy Mette — Bridey Mae Tolliver