#10 “Cheap Whiskey”- Martina McBride
The only thing whiskey pairs with better than Coke is regret — at least that’s how it goes in country songs. McBride’s “Cheap Whiskey” is a story about a heartbroken man who chose whiskey over love … and now, all he’s left with is the whiskey. “Now the things that will haunt him until the day that he dies,” she sings, “Is the smell of cheap whiskey and the sound of goodbye.” This song deserves a place on this list because of its warning that, at the very least, if you’re going to throw your life away for whiskey, at least make it top shelf.
#9 “Whiskey and You” -Darius Rucker
From the first quiet strums of “Whiskey and You,” it’s clear that listeners have entered sad song territory. While plenty of whiskey songs are sad, few are as quietly plaintive as this one. Rucker’s voice is equal parts powerful and sorrowful as he sings a broken love song: “Whiskey and you / Ain’t nothing I can do / But come crawling back to / Whiskey and you.”
In a good whiskey love song, it’s not always clear if the narrator is talking about a woman or about whiskey. So when Kristofferson sings, “She’s a part of my heart and a whole lot of my pain,” we can only guess which he means until he launches into the chorus: “Whiskey, whiskey, my old friend / I’ve come to talk with you again / Milk of mercy, please be kind / And drive this feeling from my mind.” “Whiskey, Whiskey” is a slow, deliberately paced heartbreak song about drowning your sorrows in a glass of whiskey — in other words, a perfect whiskey song.
A whiskey song can be about pretty much anything; in the case of “Drowns the Whiskey,” it’s about wanting to write a letter of complaint to the Jack Daniel’s company. Aldean and Miranda Lambert at least make complaining to a manager sound pretty; their boozy harmonies sell the song. “Whiskey’s supposed to drown the memory / I’ve gone from one to one too many / But the thing that really gets me,” they sing, “Is how your memory drowns the whiskey.”
What do you get when you add together Tritt, Marty Stuart and whiskey? A good-old-fashioned honky-tonk tune about heartbreak and heavy drinking. Probably the best song on this list for a slow square-dance, “The Whiskey Ain’t Workin’” is a straight-down-the-middle drinking song. Tritt and Stuart’s voices blend as well as whiskey and heartache when they sing lines including, “I need one good honky-tonk angel / To turn my life around / That’s reason enough for me to lay this ol’ bottle down / A woman warm and willin’ / That’s what I’m looking for / ‘Cause the whiskey ain’t workin’ anymore.”
“Daddy always said he was wrong for me / And in the end, he’d only bring me misery,” Lambert sings against guitar strums in the opening lines of “Jack Daniels.” She takes another verse of teasing the real subject of her song: He was “born and raised in Lynchburg, Tennessee,” and she says that “when I’m with him, I get meaner.” The song builds and builds in pace and volume until Lambert admits what she’s really talking about when she sings “I fell in love with Jack Daniel’s again.” It’s a deeply playful song, and hard to listen to only once.
#4 “Whiskey’s Gone” – Zac Brown Band
So many whiskey songs are downers: They’re about heartbreak, drowning your sorrows in a glass or (usually) both. That’s why the dizzyingly fast, quick-witted “Whiskey’s Gone” from the Zac Brown Band is such a nice break. Sure, if you read the lyrics, it’s still a song about turning to whiskey after a heartbreak, but the mood is definitely more upbeat. The song climaxes in a solo fight between guitars and fiddles before the vocals rip through a high-speed ode to whiskey: “Kentucky, Tennessee, you better find whiskey / Not leaving, that’s a fact / Small batch, sour mash / Red nose, red face, gonna wreck the whole place.” You might not be sad at the end of this song, but you’ll probably be out of breath.
Every list of good whiskey song needs one really heavy downer, and for this list, it’s “Whiskey Lullaby.” While the sorrow in most whiskey songs comes from a breakup, the pain in this one runs much deeper: It’s about whiskey, yes, but also self-destruction. Paisley and Alison Krauss trade haunting verses about characters tortured by love and alcohol and pain that doesn’t go away after one bad night of binge-drinking. It’s a hard listen, but in some ways, an important addition to any good drinking songs list. And, just as importantly, Paisley and Krauss are so, so good on it.
“Whiskey River” is one of Nelson’s best, and an early classic in the “whiskey songs” oeuvre. In true Nelson style, it’s pure Texas country: nothing flashy, just simple acoustic instrumentation, and Nelson returning again and again to his central plea of “Whiskey river, take my mind / Don’t let her memory torture me / Whiskey river, don’t run dry / You’re all I’ve got, take care of me.” Classic Nelson, classic country, classic drinking song; if “Whiskey River” were a drink, it’d be a whiskey, straight up.
#1 – “Tennessee Whiskey” – Chris Stapleton
“Tennessee Whiskey” has been around since 1981, when David Allan Coe released his version of the Dean Dillon- and Linda Hargrove-penned song. But in some ways, it didn’t really exist until Stapleton recorded his version for his 2015 debut, Traveller; from then on, the song’s belonged to Stapleton. There’s just no way to exaggerate how good his version of this song is, so the best thing to do is to listen to it (or, for an extra treat, watch him sing it with Justin Timberlake at the 2015 CMA Awards, a performance so incredible that it helped the song reach platinum status). There’s a lot of sadness in whiskey songs, so it’s nice to top this list with a love song.
