I know what some of you are thinking - what is a man with a big hat and shiney teeth and loads of awards from the CMA doing in this series.
The answer to that is obvious namely you clearly haven't listened to his early albums. Do yourself a favour and listen to Dwight Yoakam's first 5 albums up until 1993's This Time. As I said in my ICA over at JC's place I wouldn't bother with anything thereafter. Nothing from then on in would come remotely close to featuing here.
If this series was called Alternative Country as opposed to Americana or even New Country you could see where his early stuff fits in. Him and Steve Earle were probably mainly responsible for turning me onto country. Whereas Steve stuck to his roots Dwight became mainstream pretty quickly.
There are those who would argue that his 1986 debut album Guitars,Cadillacs, Etc.,Etc is his best I would argue that that particular honour goes to his third album Buenas Noches From a Lonely Room from 1998 on the Reprise label.
His biographer Don McLeese states the subject matter is almost relentlessly bleak, occasionally lethal and a descent into the depths of honky-tonk hell.
Thom Jurek on Allmusic points out that it goes from murderous jealousy to homicide in the first five songs. Wiki feels that Side two maintains the album's thematic grimness and melancholy.
Dwight later quipped of the song cycle, "I get moody. I kill someone. Then I get religion in the end.
Hell, if that's not Americana then I don't know what is