So, I'm listening to the playlist now and the song "Feed Jake" comes on. I know the song, but I guess I've never payed attention to the lyrics because this kind of made me say "WTF" and wonder why it's in a song about taking care of a dog...

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Now If you get an ear pierced, some will call you gay.

But if you drive a pick-up, they'll say 'No, you must be straight.'

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The music video gives a little more insight, but suffice it to say the underlying theme in the song isn't about a dog.

Don't think I've seen the video.

There's a little explanation on the wiki page...
https://en.wikipedia.org/wiki/Feed_Jake

So they should be called Butt Pirates of The Mississippi?

Their best tune was probably Dream You penned by Craig Wiseman.

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So, I'm listening to the playlist now and the song "Feed Jake" comes on. I know the song, but I guess I've never payed attention to the lyrics because this kind of made me say "WTF" and wonder why it's in a song about taking care of a dog...

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He needs someone to take care of the dog ... and everything else. Sad, sad song.

ATM2004 listed a bunch of great ones, but I think Suzy Boggus' best songs are Aces, Outbound Plane, Drive South and Someday Soon.

A great under the radar 90's country song is George Dukas' "Lipstick Promises".

Also, Shenandoah's "Two Dozen Roses" is great (it came out in '89 though).

It looks like people have put together a great list that I won't repeat.

Edit: I don't think I saw anyone mention Kathy Mattea's, "Love at the Five and Dime" and "18 wheels and a dozen roses". Never mind, it's probably because those songs came out in the 80's.

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A great under the radar 90's country song is George Dukas' "Lipstick Promises

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nice one. added it.

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A great under the radar 90's country song is George Dukas' "Lipstick Promises

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nice one. added it.

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Ditto. I had completely forgotten about that song. I have to say, I've been listening to this playlist quite a bit the past few days and have really enjoyed it. I recently set up a 90's rock/pop playlist in iTunes (don't have Spotify Premium) after starting this thread, so having a country one to go along with it takes me back to my days of walking around BBQ cookoffs with my new Sony Walkman Sport rocking my parents pager.

I'm not sure if the OP is looking for only Nashville country from the 90's, but Pat Green also put out Dancehall Dreamer and George's Bar in the 90's, which are great albums and some of his best (Carry On came out in '00 and Three Days in '01). Some good tracks from those that I listen to pretty often are:
I Like Texas
Dancehall Dreamer
Family Man
Songs about Texas
One for the Road
Southbound 35
George's Bar
John Wayne and Jesus

Roger Creager also released Having Fun All Wrong in '98, which has a lot of great songs on it (Everclear Song, Fun All Wrong, LA Freeway are the popular ones).

Whoever said Doug Stone, hit a good one. Another one of his I would add is "I'd Be Better Off...."

aTm, I like all that old PG stuff as well, but I'm keeping this playlist mainly the 90s Nashville stuff that I actually listened to back then. I didn't discover PG until late 99 when I was in college. totally with you though, those first few Pat albums are a ton of fun, before he started taking himself way too seriously.

Diamond Rio
Sawyer Brown

Ty Herndon. "livin in the Moment"great 90s country song.

Though its technically bluegrass, Alison Krauss (Union Station) was hard to beat in terms of sheer musical talent in the 90s.

What a great thread, the music of my childhood. I remember watching CMT with my grandmother, she was a huge country music fan, great memories of her.