I didn’t always like country music, in fact – growing up, I couldn’t stand twangy country music. The song that turned me around was Travis Tritt’s Its a Great Day to Be Alive but not until probably 8-10 years after its original 2000 release.
I heard this mash-up song for the first time today (it was from the CMA’s 2016). So yeah – I’m a bit behind the curve here. But I could name almost all of these, only questionable on about 2 or 3.
Here’s an article about it also for more info and list of names.
Side note, my Dad’s mom, who we called Grandma Chick-Chick loved the guy at 1:52-1:57 ish.