In the United States, there is no shortage of legendary songs that talk about whiskey. Sometimes whiskey mentions are by brand, often in metaphor, and occasionally both. Country artists especially have been singing about drowning their sorrows in the stuff for as long as their music’s been around. And like country music, which evokes images of the “real people” living in flyover country, there is something very “everyman” about whiskey. 

Sure, it’s popular in specialty wedding cocktails or sipped neat out of crystal rocks glasses. But all over America, at any given time, whiskey finds its way into our lives via shot glasses, straight from a bottle, and mixed with soda in a plastic cup. Rest assured; there are whiskey songs for every kind of whiskey drinker.

Here are ten legendary songs about whiskey that span just over 75 years of American music history.

1. ‘Cigarettes, Whiskey, and Wild, Wild Women’

“Cigarettes, whiskey, and wild, wild women” and  “they’ll drive you crazy, they’ll drive you insane.” 

We’ll start with the oldest song on the list, “Cigarettes, Whiskey, and Wild, Wild Women,” which was written by future Nashville Songwriters Hall of Famer Tim Spencer. The song has been covered by others dozens of times, and it was even translated into French for a 1959 film of the same name. However, it was first recorded in 1947 by the Sons of the Pioneers, a group that happens to be one of the very earliest Western vocal groups in the United States. 

The group, then called the Pioneers Trio, was co-founded in 1933 by Spencer, Bob Nolan, and Len Slye. Ninety years later, the Sons of the Pioneers continue their legacy of country Western harmonies. And with an extensive song catalog, they perform with their current members to sold-out crowds. 

2. ‘Whiskey, If You Were a Woman’

“Oh whiskey… if you were a woman, I’d fight you,” and as the song goes on, “I’d win (Lord knows I would).”

This 1987 track from country band Highway 101 is the first of a few examples that uses figurative language to communicate the significance of whiskey in a man’s life. In this case, Paulette Carlson’s rich, smoky voice carries an irregular kind of jealousy. Instead of being concerned about her love being unfaithful with another woman, she suggests that she would prefer that to the truth. He spends his nights out drinking whiskey. Another woman, the song says, at least has the ability to feel sympathy (though, perhaps not after the fight mentioned above).

Like plenty of country songs before it, “Whiskey, If You Were a Woman” is musically more upbeat than its attached defeatist message. This one delivers tight three-part harmonies, honky tonk piano, and pedal steel for a big, traditional country sound. Carlson’s distinct vocal style, paired with the guitar hits on the chorus, make it nearly impossible not to get sucked in and sing along. 

3. ‘Tennessee Whiskey’

“You’re as smooth as Tennessee whiskey;” and, of course, “you’re as sweet as strawberry wine.”

It seems we’ve come to the only song on the list in which “whiskey” has a positive connotation. Though it saw new popularity with this version by Chris Stapleton, “Tennessee Whiskey,” originally recorded in 1981 by artist David Allan Coe and again by George Jones in 1983, is another legendary song about the popular spirit. Chris Stapleton’s version appeared on his debut solo album Traveller, released in 2015 to much acclaim. This gruff southern rock ballad shows clear influences from blues and soul music, breaking away from the cheesy country crooning of earlier versions.

After Stapleton performed “Tennessee Whiskey” with Justin Timberlake at the CMAs, the song’s popularity skyrocketed. Two days later, it reached number 1 on the Hot Country Songs chart. And the following week it peaked at 20 on the Billboard Hot 100. As of now, the record went platinum thirteen times, selling over thirteen million copies!

4. ‘Whiskey’n Mama’

“I should’ve known better than to fool with a whiskey’n mama.”

“Whiskey’n Mama” was released in 1972 as a track on the ZZ Top album Rio Grande Mud. Unlike #2 on this list, this blues rock song flips the gender roles of an otherwise familiar trope. That is to say, a woman waiting at home for her man to come back from the bar. In “Whiskey’n Mama,” singer Billy Gibbons laments getting involved with a woman who is always out drinking. And, he implies, she’s cheating on him. 

The charm of “Whiskey’n Mama,” especially on a list full of sad and pining country songs, is in its irresistible hard rock groove.  

5. ‘One Bourbon, One Scotch, One Beer’

“I wanna get drunk, get off of my mind,” he proclaims. And it’s “one bourbon, one scotch, and one beer” that gets the job done.

While such words about drinking to forget could easily come from a country tune, this one is blues through and through. “One Scotch, One Bourbon, One Beer” was first recorded by Amos Milburn in 1953, one of three in his series of popular drinking songs released as singles.

In 1966, however, it was reimagined by John Lee Hooker, who changed a lot from the original song. His variation rearranged the words of the title. The “Hookerized” version, as his biographer would coin it, was lyrically much simpler and gave the artist room to infuse his own style into the song’s basic concept.

“One Bourbon, One Scotch, One Beer” found new life in its third decade as well, appearing on the 1977 self-titled debut album from George Thorogood and the Destroyers. Thorogood paired it with another John Lee Hooker song called “House Rent Boogie.” The medley, which Thorogood used as a vehicle for storytelling, was apparently given an “Okay, go ahead” by Hooker himself when Thorogood presented the idea. 

6. ‘Whiskey Lullaby’

“And we buried him beneath the willow,” the song melodically chants, “the angels sang a whiskey lullaby.”

This duet between country star Brad Paisley and bluegrass musician Alison Krauss won the CMA Song of the Year Award in 2005. “Whiskey Lullaby” takes the common theme of drinking to forget to the furthest possible conclusion, describing a man who drinks himself to death due to a breakup. The second verse, sung by the incomparable Krauss, talks about the man’s ex-lover feeling so much guilt over his death that she, too, eventually “put that bottle to her head” and subsequently “pulled the trigger.”

“Whiskey Lullaby” has a complicated relationship with reality, as both deaths show signs of suicide while also detailing a history of drinking whiskey to cope with their pain. We, as listeners, don’t get to know if these deaths were actually due to alcoholism, alcohol poisoning, or a broken heart — or whether they were truly intentional deaths. What we can know for certain is that no matter the answer, the song is tragic. It is easily the saddest song on the list, even as others deal with similar subjects. That said, it is lauded and beloved by many in spite of its emotional tone. The vocal stylings of two legendary country singers make the song impossible not to include on this list.

7. ‘Poison Whiskey’ 

“He drank ole poison whiskey ‘til it killed him dead.”

In contrast with the aforementioned saddest song, both emotionally and musically, is the 1973 Lynyrd Skynyrd rock jam “Poison Whiskey.” The subject of the song, which appeared on the legendary band’s debut album, is a seemingly absent father who had a drinking problem. It is presented as legend, something the singer has only heard in stories. The man’s doctor warned him that he would drink himself to death. And that is exactly what happened.

The song is ironic given the band’s proclivity to perform drunk, but “Poison Whiskey” is less about the story than it is about rock. Immediately the bass, drums, and rhythm guitar establish a groove with hits of wailing organ, quickly revealing impressively technical ensemble musicianship.

8. ‘Whiskey Under the Bridge’ 

“Oh, it ain’t no big deal; it’s just whiskey under the bridge.”

“Whiskey Under the Bridge” is a song written and released by country duo Brooks & Dunn in 1995. While the subject matter is familiar to readers of this list, the song is actually pretty hopeful. As its title suggests. “Whiskey Under the Bridge” is sung from the point of view of a man who is mostly beyond his heartbreak. Although, it’s certainly possible that he is trying to appear more “over it” than he actually is. After all, the song seems to attempt to convince his dance partner, if not himself, that there’s no heartbreak. And it’s “a brand new love can’t fix.”

The cheerful two-step evokes images of cowboy hats, boots, beer drinking, and line dancing in a honky-tonk. It might just be enough fun to keep the broken heart at bay. 

9. ‘Whiskey River’ 

“Whiskey river, take my mind. Don’t let her memory torture me.”

Prolific songwriter and whiskey drinker Willie Nelson apparently still opens every show with “Whiskey River,” which he released in 1973. Yes, that’s right, the 90-year-old outlaw country icon is still touring! Beyond writing his own songs, Nelson has written titles for big stars — most notably Patsy Cline’s hit “Crazy.” 

Interestingly, “Whiskey River,” which continues to be Nelson’s signature song, was actually written and originally recorded by his good friend Johnny Bush. Thirty years later, Nelson would have the honor of inducting his lifelong buddy into the Texas Country Music Hall of Fame.

The beauty of this one is in simple, soaring harmonies and a touch of old-timey country charm.

10. ‘Tennessee’ 

“It’s beefsteak when I’m working, whiskey when I’m dry, and sweet heaven when I die.”

Gillian Welch is a singularly gifted songwriter. But she is perhaps best known for her contribution to the widely popular O Brother Where Art Thou soundtrack. Also featuring “Whiskey Lullaby” vocalist Alison Kraus, the soundtrack received the coveted Grammy Award for Album of the Year back in 2002. The very first year, there was a Grammy Award for Best Folk Album. And Gillian Welch’s album The Harrow and the Harvest lost the award to the debut album from a folk duo called The Civil Wars.

The critically acclaimed 2011 record has no bad songs, but “Tennessee” is arguably the best on the album. The song is a slow, confessional midpoint on an album that represents “ten different kinds of sad,” according to Welch’s creative (and romantic) partner Dave Rawlings. The sadness of “Tennessee” is bittersweet and nostalgic.  

Maybe that doesn’t qualify it as the saddest song on this list, but one line from the song stands out as particularly suitable to describe the list’s overall theme: “Of all the little ways I’ve found to hurt myself, well, you might be my favorite one of all.” 

Whether the line is directed to a man, a woman, or whiskey herself, it’s a sentiment that many of the whiskey drinkers on this list always seem to say. 

The next time you listen to your favorite tunes, see if you can spot references to whiskey. It’s a perfect ingredient and inspiration for some of the music world’s more legendary songs.