He's not wrong often, but he's wrong here. See, the list of which he speaks actually really, really sucks. I kind of had a feeling it would, when I saw that number fifteen is "Angry All the Time" (that song sucks completely independently of Tim McGraw's version).
With the possible exception of number nine (and maybe 14; I'm not at all familiar with James McMurtry), only number two is the best song from any given artist.
Now, almost none of the songs are bad, not by any means, but there are others that are better. Sometimes a lot better. I mean, I do love "Down the Road Tonight", but that's not even close to Hayes Carll's best song. Even "Drunken Poet's Dream" is better, and he's done far better songs than that.
Equally baffling is the choice of "Somewhere Down in Texas" to represent Jason Boland and the Stragglers. Now, these guys should rightfully be the Red Dirt gateway drug. There is simply no one in country music today with a better voice than Jason Boland. He's up there with George Jones as far as pure sound goes. And "Somewhere Down in Texas" is a great song. But you can stack up almost anything from Comal County Blue against it, and it would lose. The title track off that album is, as far as I'm concerned, his absolute best song, but that same album gives us "Bottle By My Bed", which is ranks right up there with George Strait's "Poison" or, well, any regretful drunk song.
Erik did cover the issues with the number one song, so I'll leave that alone here. (I'd have gone with "Levelland" personally, but "Shades of Gray" is also acceptable.) Instead, I'll bitch about a couple of other points.
For one, the inexplicable pick of "The Weary Kind" rather than "Bread and Water" from Ryan Bingham makes me strongly suspect they never heard of the man before Crazy Heart came out. I know the latter song isn't exactly high tone, but the guitar work alone far surpasses the admittedly-wonderful song that's actually on the list. And it's that which makes me think the folks who compiled the thing were trying to come across as critics rather than people who actually listen to the music.
And the last thing...there are some absolutely baffling exclusions. No Roger Creager is bad enough (ignore if you must the silly goodness of "The Everclear Song"; this is the same man who did "Having Fun All Wrong"), but these hacks totally ignored Ray Wylie Hubbard. Which really tells you all you need to know, but it would have been a short blog post if I'd led off with that.