With its brewing (and drinking) tradition as well as its railroad-hub history, the city of Milwaukee has served as inspiration for many country songwriters over the years. A few of those songs have become honky-tonk hits by some of the biggest names in country music history. Others are little-played B-sides by Nashville nobodies. We poured a few beers, pooled our favorites together, and ranked them 1 through 20 in this definitive (pre-’90s) Milwaukee-themed country music playlist.

20. Sharon Whitbread – “The Married Ladies of Milwaukee” (Pye Records, 1975)

Background: Is this a country song? Maybe not. But it has a Bobbie Gentry country-soul-jazz-pop vibe to it, and we needed a 20th song to round out the list. Plus it’s weird as hell! We must have listened to this song 25 times and we still can’t quite figure out what Sharon Whitbread is trying to say about the married ladies of Milwaukee. Regardless, it’s a fascinating track by the English singer (by way of Singapore).

Sample Lyric: “Susan is learning all about acupuncture / Jane is still talking to her plants / And now Joanne’s occupying all her mornings by trying the most revealing yoga stance / Elaine has learned the art of kung fu / She had to think of something to do / The married ladies of Milwaukee pass the time of day in a very extraordinary way”

19. Jerry Berens “J.B.” – “Save The Milwaukee” (Mill Town, 1984)

Background: Jerry Berens, of South Dakota, was campaigning to save the fledgling Milwaukee Road railroad line with this song. Sadly, his efforts failed. By 1986, the Milwaukee Road was completely defunct, with the tracks mostly being absorbed by other lines.

Sample Lyric: “From Butte in Montana and east to St. Paul / That lonesome midnight whistle will not be heard at all / So all of us who are concerned must rally, can’t you see? / To keep our lives productive, we must keep the Milwaukee!”

18. Uncle Smoky – “The Milwaukee Boys” (RCA Records, 1982)

Background: This isn’t exactly a song about Milwaukee. It’s a song about Milwaukeeans—specifically, a group of Milwaukeeans who drive up to Ontario for a week every summer to go fishing (and drinking and singing).

Sample Lyric: “They come runnin’ up here for a week every year / Runnin’ from their jobs and their wives so dear / They come a long way, and they have a lot of fun / Drink until 3 and then risin’ with the sun / Oh, yeah”

17. Ray Griff – “Drinkin’ Old Milwaukee Dry” (RCA Records, 1983)

Background: This makes two Canadians in a row, and it’s the first of a handful of artists on this list intent on attempting to drink Milwaukee dry. The song came out in 1983, and it definitely sounds like it.

Sample Lyric: “I was sittin’ with my lady in a smoky bar in Wisconsin / I’d been laid off at the factory, so I thought I’d take a vacation / It was well into the evening and the feeling that we had was high / On our way to Canada, we were drinking old Milwaukee dry”

16. Larry Lee Phillipson – “First Night Back In Milwaukee” (Phillipson Records, 1971)

Background: Larry Lee Phillipson, a Rockabilly Hall of Famer, was a Milwaukee native. This track is about trying to make it in Nashville as a songwriter only to find that his wife was cheating on him while he was away. This isn’t the last time Phillipson appears on this list.

Sample Lyric: “Now I know why she never wrote me / As I peer through the smoke-dimmed light / By the bar, she sits with her lover / I’ve gotta do some forgetting tonight / Hey, waitress, set me up another / When it’s gone, fill the glass up again / It’s my first night back in Milwaukee / And it calls for a celebration”

15. The Lost Marble Band – “Brewers Have It All” (Lost Marble Records, 1982)

Background: How can you not love a bluegrass song about the 1982 Milwaukee Brewers?

Sample Lyric: “Baltimore was going great, but our guys didn’t care / They left Jimmy Palmer standing in his underwear / And then the Angels came to town / They already took a pair / But when they met old Harvey’s boys, they didn’t have a prayer”

14. Larry Phillipson (The Swamp Jumper) – “The Milwaukee Road” (Phillipson Records, 1972)

Background: Larry Lee Phillpson, who dropped his middle name on this release, delivers a catchy rockabilly song about traveling via train along the Milwaukee Road to get back to his lady in Cream City.

Sample Lyric: “I’m gonna rock / I’m gonna ride / I’m gonna roll / On the old Milwaukee Road / You’ve heard a lot of stories about the trains in this great land / About the trains from Tennessee down toward Alabam / Here’s a story about a train that’s one you all can see / Traveling through the northland on the way to Milwaukee”

13. Charlie Poole and the North Carolina Ramblers – “Milwaukee Blues” (Colombia Records, 1931)

Background: This ode to hobos, hitching trains and the Milwaukee Road railroad system has become a classic folk tune and has been covered by dozens of performers, including great renditions by Don Flemons and the New Lost City Ramblers.

Sample Lyric: “I left Atlanta one morning before day / The brakeman said, ‘You’ll have to pay’ / Got no money, but I’ll pawn my shoes / I want to go west, I got the Milwaukee blues / Got the Milwaukee blues, got the Milwaukee blues / I want to go west, I got the Milwaukee blues”

12. Lee Hazlewood & Ann-Kristin Hedmark – “Old Milwaukee” (RCA Records, 1975)

Background: The vocals make this song. Lee Hazelwood, who originally rose to prominence for his work with Duane Eddy and Nancy Sinatra, over-pronounces his words and occasionally falls behind the beat, almost as if he’s as drunk as the character he plays in this booze-soaked tune. Swedish singer Ann-Kristin Hedmark counters with a sultry smooth delivery. This 45 has become collectable, fetching an average of over $70 per sale on Discogs.com.

Sample Lyric: “Old Milwaukee has a brewery / Where they’re brewing kegs of beer / Pull the tapper / Fill it / Drink it all up / Fill it / Gulp down one more / Fill it / Head for the door / Make it halfway to the table / Falling headlong out here / Love these Milwaukee brews”

11. Terry Smith – “Something Brewing in Milwaukee” (Rhinestone Rooster, 1987)

Background: This straight-forward country cheating song sounds like it should’ve been released in 1970, not ’87. Terry suspects his gal is seeing someone else while she’s in Milwaukee. And he’s almost definitely right because she’s not answering his calls, not calling him, and not replying to his letters. Plus her mom sounds weird when Smith talks with her. Take a hint, Terry!

Sample Lyric: “I’ve tried to call, but there’s no answer, and it’s 3 a.m. / It’s been that way for three nights in a row / And she hasn’t called a time for me in almost 20 days / Sometimes I’m not too smart, but now I know / There’s something brewing in Milwaukee”

10. Kitty Wells – “Old Milwaukee’s Talking” (Ruboca Records, 1980)

Background: With one of her final singles, the original Queen of Country Music warned that Old Milwaukee will make you say “things that you’ll regret with the coming of daylight.” It’s far from her most memorable work, but it’s good enough—kind of like a can of Old Milwaukee.

Sample Lyric: “I’ve heard it all my life / And I guess this time I’ve bought / The sayings of a drunk man is a sober man’s thoughts / It takes alcohol to make you say what’s on your mind / And Old Milwaukee’s doing a bang-up job this time”

9. Willie Gregg – “The Girls in Milwaukee” (Stop Records, 1972)

Background: There’s a good chance this one would be higher on the list if we could find a cleaner copy of the 45. Unfortunately, we haven’t tracked any down online or in the wild. In fact, we can barely find any info at all about this quirky lament to the fate of Milwaukee women. That just makes us like it a little more.

Sample Lyric: “Oh, the girls in Milwaukee are walking the streets / But not for the reasons you think / They’re searching the taverns for the men in their lives who are hooked on the hometown drink”

8. Wilburn Brothers – “Milwaukee, You’re In Trouble” (MCA Records, 1975)

Background: One of the final singles in the Wilburn Brothers’ storied country music career, “Milwaukee, You’re in Trouble” flipped the script on the Milwaukee drinking song. Instead of turning to Milwaukee’s beer and bars after losing a love, the main character in this song gives up the nightlife in favor of the “sweet love” of his newfound woman.

Sample Lyric: “Now, Milwaukee, you’re in trouble / Cause she offers more than you can / Yes, Milwaukee, it’s all over / Her sweet love replaced that old bottle in my hand”

7. Larry Cheshier – “They’ve Got Millions In Milwaukee” (Warner Bros. Records, 1976)

Background: There’s an old trope in country music that “once George Jones sings a song, it’s been sung.” But even though The Possum’s version, which came out a year after the original, is a very solid effort, especially during an era in which Jones was badly losing his battles with alcoholism, drug abuse and mental illness, we give a slight edge to the Cheshier cut. But, don’t worry, you’ll see Jones a little later on this list.

Sample Lyric: “They ought to put my picture on the beer can / So that woman of mine can see / They’ve got millions in Milwaukee / Thanks to guys like me”

6. Jerry Moore & The Drifters Four – “Drink to Milwaukee” (Illini Records, 1973)

Background: This 45 was put out on Illini Records, of Springfield, Illinois, but evidently, lead singer Jerry Moore, who wrote the song, had roots in Milwaukee—”that old town of mine.” He penned a good old drinkin’ tune with loads of charm.

Sample Lyric: “You thought when you left me that I’d cry the whole night through / That I’d sit at home and wait for you / But I found another friend who never lets me down / That’s why I love Milwaukee like I do”

5. Billy Walker – “Till I Drink Milwaukee Dry” (First Generation Records, 1981)

Background: When we saw Joshua Ray Walker play a few weeks ago, he lifted the “sit right here in Dallas till I drink Milwaukee dry” line from this song and dropped it into his song “Bronco Billy’s.” We instantly morphed into the pointing Leonardo DiCaprio meme. That subtle hat tip from a current Texas country artist to this 1981 “Tall Texan” track was the cherry on top of a great set.

Sample Lyric: “I’ve got a heartache from being much to lonely / Oh, but a cowboy just ain’t supposed to cry / I came in here to get rid of a hurt condition / And I’ll sit right here in Dallas till I drink Milwaukee dry”

4. Charlie Walker – “Gonna Drink Milwaukee Dry” (RCA Victor, 1973)

Background: Texas’ Charlie Walker was a master of the honky tonk drinkin’ song, and this classic track appeared on one of his best albums—Honky Tonkin’ With Charlie Walker.

Sample Lyric: “Play me songs, make ’em blue / Bartender, bring me barrels of brew / Call the man where they make it at / And tell him to send every can he can / And keep ’em working overtime / Cause tonight I’m gonna try / To drink Milwaukee dry”

3. Don Acuff – “Miss Milwaukee Brew” (KD Records, 1985)

Background: Private label gems like this are exactly why we love digging through dollar bins. The song is solid, and the musicians are great, but the stars of the show are clearly Don Acuff’s untamed vocals and the priceless lyrics. If we are to believe the internet, Don may be a cousin of famous country trailblazer Roy Acuff. But since Don was almost certainly born many decades after Roy, the cousin claim seems almost as tenuous as the song’s rhyming structure, which includes the absolutely audacious rhyme of “fun” and “mon.” Yes, that’s “mon,” as in the first half of “money.” We love this song.

Sample Lyric: “She never locks the door / Or keeps me up til 4 / But she sits with me while I watch football on TV / She never complains / Or calls me by the wrong name / Let me introduce you to Miss Milwaukee Brew”

2. Jerry Lee Lewis – “What’s Made Milwaukee Famous (Has Made A Loser Out Of Me)” (Smash Records, 1968)

Background: This country staple, which Jerry Lee Lewis popularized, is a tip of the cap to Schlitz’s memorable slogan: “The beer that made Milwaukee famous.” And The Killer rode it to a top 10 Billboard country hit.

Sample Lyric: “Baby’s begged me not to go / So many times before / She says love and happiness / Can’t live behind those swinging doors / Now she’s gone and I’m to blame / Too late I finally see / What’s made Milwaukee famous / Has made a loser out of me”

1. George Jones & Brenda Carter – “Milwaukee, Here I Come” (Musicor Records, 1968)

Background: Jones, a country music superstar, and Carter, a 17-year-old newcomer, played a Milwaukee couple in this 1968 duet about returning back to Wisconsin from Music City. The classic tune topped out at No. 13 on the Billboard country singles chart and has been recorded by dozens of other artists, including Porter Wagoner and Dolly Parton, Jimmy Martin, John Prine and Melba Montgomery, and Milwaukee’s own .357 String Band.

Sample Lyric: “Milwaukee is a-where we were before we came here / workin’ in a brewery, making the finest beer / You come to me on payday night said, ‘Let’s go to Tennessee’ / So we came down to Nashville to the Grand Ole Opry.”

Here’s a link to the full playlist 1-20…

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