Ladies Love Outlaws according to Tom Rush and the song's writer, Lee Clayton, but a lot of guys do too, in a manly way, of course. :-) So:

Marty Robbins was one of the best singers Country (and Western) has ever known and he wrote some brilliant songs as well. His Big Iron is a cinematic experience (as is the much more famous El Paso, both are from his monumental Gunfighter Ballads and Trail Songs LP), a near-complete Western movie in just four minutes. The only things missing are the voluptuous saloon keeper with a heart of gold and the virtuous maiden to embrace him [SPOILER ALERT] after he vanquishes the villainous Texas Red. With Grady Martin grabbing some gutsy gut-string guitar fills (try saying that 3 times fast). Martin also does the wonderful guitar work on El Paso.
Big Iron

A bunch of folkies, including Joni Mitchell and John Denver, covered John Phillips' western epic, Me and My Uncle but for me the Grateful Dead did the definitive version on their Skull and Roses LP. Jerry Garcia's alternatively stinging and fluid, lead guitar licks heighten the tension and Bill Kreutzmann does a beautiful job of drumming to the song. I think the Dead were peaking in 70-72 (not in a psychedelic way, although...). Me and My Uncle

Pretty Boy Floyd, Woody Guthrie's Robin Hoodesque portrayal of an outlaw from his home state contains the memorable line "As through this world I ramble I meet a lot of funny men, Some rob you with a six gun and some with a fountain pen." Sung by the inimitable Roger McGuinn off of the Byrd's highly influential Sweetheart of the Rodeo album it features American musical giant John Hartford playing some very crispy banjo. Pretty Boy Floyd

A few more quickies:

Ry Cooder, Billy the Kid- From "Into the Purple Valley" which was my intro to Cooder and is still one of my favorite LPs.Billy the Kid

Pharis and Jason Romero, Wild Bill Jones- In addition to being a fine performing duo this pair from British Columbia also make some of the most beautiful and sought after banjos on the planet. Wild Bill Jones

Richard Thompson's 1952 Vincent Black Lightning is a modern classic. Inspired by a true story RT sings this to one of the greatest solo guitar accompaniments I've ever heard with a cajun-like fiddle tune on the top strings and an alternating bass on the bottom strings played in Malagasy tuning, GCDGBE. Interestingly, that's probably a Vincent Rapide pictured in the video as Lightnings (and Black Shadows) had black-painted casings. 1952 Vincent Black Lightning

Jimmy Cliff, The Harder They Come- From the film of the same name, a very cool flick with performances from many of the first generation Reggae stars. Mr. Cliff passed on recently. The Harder They Come   

Whoa,those quickies weren't quite as quick as I intended.