He was the first one I thought of.
Van Lear Mine and She Wore Red Dresses – dying at work and killing your ex – not the stuff of mainstream country radio! 
These guys
Lonestar 92.5 (Dallas/Fort Worth, Texas)
play a lot of outlaw country with a fair amount of Southern rock & blues.
(my favorite station!)
Some artists that are my favorite. I don’t know if they would fit into whatever country faction you’re trying to define here, but. . .
Dwight Yoakum
Lucinda Williams
Steve Earle
Ray Wylie Hubbard
Ryan Bingham
Wayne Hancock for an old honky-tonker in the Hank style.
Live at The Old Quarter may be the best Townes album. His earlier stuff is over-produced to modern ears, even though the songs are great. And some questionable stuff has come on the market after his death, thanks to those who tried to help his career, those who tried to harm it, & his last ex-wife.
Steve Earle (a Townes devotee) is a fine songwriter who has worked in several musical styles–folk, bluegrass, Irish, honky tonk & blistering rock. Lyle Lovett’s Step Inside This House is a tribute to Texas songwriters (including Townes). A bit folky–but you’ll see the influences.
“Outlaw Country” was a marketing term. But don’t blame the artists thus labeled. Honky Tonk Heroes, in which Waylon Jennings sings the tunes of Billy Joe Shaver, may be the very best of that genre.
Do explore other works of the artists you’ve listed. Merle did a fine tribute to Bob Wills–historical research that you can dance to. (Wow–it’s a bit pricey. How about this tribute from Asleep At The Wheel?)
Eventually you’ll be ready for the hard stuff. Buck Owens & The Buckaroos (ask Dwight Yoakum!) George Jones. Lefty Frizzell.
Yee-haw!
Train wrecks, mine disasters & faithless lovers are old, traditional topics in country music. But you won’t hear those tunes on mainstream country radio.
Well, the Dixie Chicks recorded “Good Bye Earl.” But some country stations still consider them unAmerican.
And Ry Cooder recorded “That’s the Way The Girls are From Texas”–definitely a cautionary tune for those contemplating stepping out on Texas women. But he’s hung out with those Cuban Commies!
(Yes, mainstream country music radio sucks. See Murder On Music Row.)
Don’t forget to check out Jerry Jeff Walker!
Originally seen as a folkie at Houston’s Sand Mountain Coffee House. Just before he left town to join a folk-rock band, he sang “Mr Bojangles” to the audience. But he came back to Texas in time for The Great Progressive Country Scare of the 1970’s.
See also alt.country, country rock, etc.
OP, I’m hoping you’ve heard Johnny Cash’s “Live at Folsom Prison” album, if not get it, get it ASAP. Cocaine Blues rules.
Hank III rocks too, especially his "Straight to Hell"and “Risin’ Outlaw” albums.
Check out the Loretta Lynn and Jack White collaboration, “Van Lear Rose.”
And if you’re into the whole Rockabilly thing, you can branch out into stuff like The Meteors and Southern Culture on the Skids, and even into punk bands like The Misfits and Social Distortion.
I tried him, but about all I liked is: Up Against the Wall Redneck Mother (little bit NSFW, Confederate Flag, bikinis and thongs, no nudity.)
Well, alot of those guys were doing their thing probably before your parents were even born, so that may be one reason.
-FrL-
Try this.
Yes. Also- and I may get some groans for this, you should check out Dolly Parton. She’s no oulaw, but there’s a darn good reason that Tom T. Hall was “wishin’ he had a Dolly Parton Tape” in Spokane Motel Blues.
Her voice is just magical, and for music you can “feel,” she can’t be beat. I think of her as the antithesis to the wavery/quavery Celine Dion/Barbra Steisand/American Idol style of vocals. Checkout any of her early stuff- I like “Hello, I’m Dolly” a lot. Jolene is the song that really did it for me- listening to it a few times on a “best of” compilation LP that I bought just because I liked the sleeve picture (here) took her from punchline to goddess in my eyes. I say punchline because as a child of the 80s with parents who didn’t care about “Country” in any way, I only knew of her as some singing chick with big boobs who had her own theme park. I think what gets me about her voice is that she never seems to be straining- it’s like she just opens her mouth and the heart pours out. Also she seems to have a great sense of humor, even in some of the weepier songs.
ETA- here she is on Porter Wagoner- what a little cutie! youtube
Then you’ll love this live performance. The monologue before the song is classic 
Robbie Fulks
The Blacks
Johnny Dowd