Between their list and the reader's list, they got "Concrete Angel" (first music video I ever cried to, guys, seriously watch if you've never seen it), "Whiskey Lullaby", "Travelin' Soldier", and "Christmas Shoes" (which I first heard done in country). (The other sad song I think of is "Paper Angels".)
As for the 'twist ending' ones, the two I can think of right now are "Three Wooden Crosses", "The Little Girl", and, of course, "The Greatest", which was my favorite song ever as a child.
Other country songs I've loved for a while: "Goodbye Earl" (which, when played in the cafeteria during spirit week, all the girls sung/hollered along to, and the music video has Madame Director AND Joey Penhall, and is pretty awesome anyway), "Wild One" (because the first two lines were me until about age nine), "One Voice" (which was released just over a year after Columbine, so the last verse really struck me), "How Do You Like Me Now", "Celebrity" (a hilarious song and an even more hilarious video) and "Online", and, heck, "Alcohol" and "I'm Gonna Miss Her", because Brad Paisley is kinda of the hottest funniest guy evar and I wish to marry him.
...I totally didn't realize he's the one that did "He Didn't Have to Be". I LOVE that song. I have since I first heard it