Sometime soon after college I bought Across the Borderline by Willie Nelson, specifically because I hated country music and figured I oughtta give it a shot. It became my favorite album, up until I bought Teatro. Some of Nelson’s other stuff strikes me as kind of saccharine, but I love these two albums, and they moved me on to Johnny Cash and a few other country singers.
Apparently, you’re me.
CMT had videos, the other “music” stations had moved on. I started listening to pop-country. I listen to less now than I did then because it’s now all the same song. I still will stop on country songs when I’m scanning through channels in the car radio.
None. In my case, it was a program which was on Radio 3 every Sunday afternoon, back when I was a teenager (still is). At such times, every station except Radio 3 and Los 40 would be soccer, soccer, soccer, soccer or soccer; I started listening to Toma Uno simply because they were different from Los 40 (which played the Top 40 all week round), but I soon realized that in most cases I could understand the lyrics quite well and then I started actually paying attention. Queen had already taught me that in English you can write things down the way you say them (The Works has 3 or 4 different versions of “because”); Dolly, Kenny and “the man with the braids” improved my vocabulary.
So, it started as a way to avoid the soccer and the single hits chart available to me at the time, and continued as a way to improve my English. Eventually I grew to find artists I liked and others I don’t, but I can’t say that it was an individual artist unless you let me count the DJ 
My sister-in-law turned me on to Uncle Tupelo and Drive By Truckers. Uncle Tupelo led me to Son Volt, Jay Farrar’s country band. I don’t listen to Son Volt much anymore, but it was a bridge to other artists.
Drive By Truckers led me to Jason Isbell, former DBT member and god of Americana.
Meanwhile, my friend turned me on to John Prine, which led me to Prine superfan Kacey Musgraves, and through her the Texas/Oklahoma country scene: Sunny Sweeney, The Trishas, Turnpike Troubadours, Jason Boland and the Stragglers, Whiskey Myers, John Moreland, and so on.
Lastly, an interest in the music of my native Kentucky led me to a number of artists: Sturgill Simpson, Chris Stapleton, Kelsey Waldon, Angaleena Presley, Chris Knight.
Damn straight.
I’m obviously a later convert than most of the above posters. For me, the conversion came via Trisha Yearwood. I had a woman I was dating in 1997 who liked some country, especially Trisha. I got hooked on one of her Greatest Hits compilations that came out that year, as I recall. That led me to listening to other similar artists. The thing I found about country was that the artists were more willing to sing about non-love things (pop-rock gets so depressingly identical with its themes). In the years since, I’ve continued to winnow the junk country in order to find the very enjoyable kernels.
Example: Chely Wright’s “Emma Jean’s Guitar”. What a wonderful song. Reminds me of music from the 60s and early 70s, when so many different genres were able to get play time, and songs were about all sorts of different things. 
The ink is still wet on my conversion papers. Maybe the last year or so at most.
You just get tired of rock/pop/self-indulgent juvenalia, the more so when the juveniles are older than you are. A real grownup singing well-crafted lyrics about real adult feelings and actions makes all but the very best pop singers sound so… juvenile and narcissistic. You have to wonder about a 60yo who’s been married for decades writing chick-chasing songs.
Just around my last year of high school, Canadian cable launched the “New Country Network”, which eventually switched to CMT Canada. I started checking it out and ended up getting hooked.
The one song I remember liking very much first of all was by Canadian singer Lisa Brokop: “Take That.” This was in 1994-1995
And you are me! I have moved on too because of the sameness, but I still enjoy the 90s stuff. Alan Jackson had some timeless ones – I still wonder that someone wrote something as perfect as Remember When.
I am at work and checked out the lyrics. I gotta listen to that song when I get home.
I had no interest in country music when I moved to Nashville about 17 years ago. Of course here, everything is kind of steeped in it. My first step was listening to a ‘best of’ Johnny Cash compilation, and realizing I kind of liked it (and I liked that he sang in such a low register that I could sing along with). It was also around the time that the movie O Brother Where Art Thou came out, and I started listening to that soundtrack, which opened me up to Allison Krause, Ralph Stanley, and others.
I was hooked when I started listening to Old Crow Medicine Show, and then a few years ago I started learning to play both the fiddle and mandolin. I’m deep in, now.
Mandolins. Jeez, you need an intervention ASAP. 
Not to turn this into a favorites list, but I think anyone reading this thread, pro or con, would enjoy this Guy Clark piece. I think there’s even a mandolin in there somewhere.
You might know this already, but Crazy was written by Willie Nelson, well before he became a star in his own right. He’s written many brilliant songs, if you’ve not listened to much of his stuff.
Oh yeah, I thought about name-checking Willie in that post, but didn’t. Learning about him and his music was part of realizing there is a lot I like about Country music.
One of the few radio stations we could get clearly at UIUC was WMAQ from Chicago. All country. We listened to that, I dated a guy who was into country, and the rest was history. I really liked country up until the late 90s when it went pop/country. But give me Waylon, Hank, Patsy, and I’m happy. Hell, I even like the Statler Brothers.
In 1987 I read a review of the Randy Travis album “Always and Forever”. It might have been in the Wall Street Journal or the New Yorker. Definitely a publication not associated with country music. The reviewer was raving about the album, and I decided to check it out. That led to many, many years of always having the radio tuned to country, and watching all of the country music awards shows, and becoming familiar with much of the country music catalogue. Eventually the local country radio stations I listened to switched to something else, and country music kind of passed me by – I don’t like much of the current stuff. But I can definitely date my interest back to that specific album.
I started listening late 90s. I sing. I started as a child and I’m pretty good. Anyhoo, it’s fun to sing with. I also like the fact that some of it has a real sense of humor, about itself or about life. It isn’t always so serious.
Alan Jackson’s cover of “Mercury Blues.” Specifically the first slide guitar solo.
Beck. Sissyneck. “I got a stolen wife, and a rhinestone life, and some good old boys. I’m writing my will on a three dollar bill, in the evening time”. Beck made country music “cool” to thirteen year old alterna-geek me in the 90s. He did the same thing with rap/hip-hop.
Though Wilco had a big part to play, considering I found alt-country and Americana before moving into “plain-old” country.
I still don’t like the Luke Bryans and FGLs of the world and the bland pop shit they play on the radio. So if that’s what you mean by “country music”, count me out. But at this point, most country music fans agree with me. Even Taylor Swift realized she couldn’t keep lying to her fans about what kind of music she played anymore. Now we got Sturgill Simpson and Jason Isbell getting nominated for Grammys, so I feel like “real” country music is poised for a comeback.
When I finally got a car with a radio, I used to listen to oldies stations. I’d alternate between two which were close together on the dial. One day, I accidentally got a nearby country music instead. Two songs which played back to back that got me started on listening to country music were “She’s Somebody’s Hero” by Jamie O’Neal and " “Something to Be Proud Of”. by Montgomery Gentry. I still hear the latter occasionally.
So I talked to Sturgill for about five minutes, mostly about his good friend and mentor John Prine, and finally had to admit that I didn’t listen to much country. He patted my arm and said, with all sincerity, “Neither do I.”
Incredibly nice guy and I think we’ll see him on the outlaw list when it’s updated.