The country landscape doesn't change as often as pop, so you can start in a lot of different places. Her early duo stuff with Porter Wagoner is middling, in my opinion. If I were you, I'd go straight into the Jolene album or the 9 To 5 And Odd Jobs album. If you enjoy modern country (Miranda and Carrie, especially) then her newer stuff like Blue Smoke and Backwoods Barbie might appeal to you. Better Day, too, but it's a bit more gospel-y than the others.
My personal, all-time favorite song of hers, though, is a soundtrack single she did for the film Transamerican. The song is called Travelin' Thru, and it's ridiculously inspirational. Some of the best songwriting I've ever listened to.
This is SO HELPFUL! Thank you!
I prefer old country (I grew up on Loretta Lynn and even got to see her live a few years ago ) to new country by a long-shot, so I'm going to start with those and slowly make my way up. Everything I've heard up to this point has been amazing and completely sold me on giving her albums a fair chance. She has such a unique voice.
I'm so embarrassed listening to "Save The Last Dance For Me" right now; the amount of times I've listened to Michael's rendition and never even bothered to listen to the original. I never realized Dolly had so many undeniable classics to her name!
After I finish Cupid's suggestions I'll listen to "Travelin' Thru" and then 9 to 5.
Remalicious definition make them flops go loco
They want my eggo, want my trix, and now they want my coco (puffs)
You can quote me, but you can't drag me
I ain't taken, but you can't have me
I got reasons why I report 'em
Uglees just come and go like seasons
Remalicious definition make them flops go loco
They want my eggo, want my trix, and now they want my coco (puffs)
You can quote me, but you can't drag me
I ain't taken, but you can't have me
I got reasons why I report 'em
Uglees just come and go like seasons
) to new country by a long-shot, so I'm going to start with those and slowly make my way up. Everything I've heard up to this point has been amazing and completely sold me on giving her albums a fair chance. She has such a unique voice. 
I never realized Dolly had so many undeniable classics to her name!
Lord, you weren't exaggerating, Citrus.
