12 Songs About Doing Time

Is a Jail Sentence Inevitable for the Characters of "Somethin' Bad"?

Back when country music was the artistic province of poor, uneducated white people, there were lots of songs about folks landing in jail or on chain gangs or even on Death Row. But now that country has moved to the suburbs, about the worst that can happen — vis-à-vis the law — is getting a ticket for driving your pickup too fast.

So leave it to Miranda Lambert and Carrie Underwood to have the brass to inject some starch back in country music’s spine and, in so doing, raise the specter of a serious clash with the cops.

In “Somethin’ Bad,” their new single, Lambert and Underwood pick up “a girl in a pretty white dress” and head south with her, an action that leads to this assessment: “‘Bout to tear it up down in New Orleans/Just like real life Thelma and Louise/If the cops catch up, they’re gonna call it kidnapping/Got a real good feeling something bad about to happen.”

Does jail lie ahead? It does if you keep reading this chronological list of 12 country songs about doing time.

“The Prisoner’s Song,” Vernon Dalhart (1925)
Told from the viewpoint of a man about to be incarcerated, “The Prisoner’s Song” was one of the first “country” records to be a national hit. It predates by two years the fabled Bristol Sessions that launched the careers of the the Carter Family and Jimmie Rodgers. Why the man is going to jail and for how long are matters never addressed. But the song gave us the immortal line, “Now if I had wings like an angel/Over these prison walls I would fly.” As a narrative, the song falls short, but it sparkles with vivid images.

“In the Jailhouse Now,” Jimmie Rodgers (1928)
This is a series of lighthearted vignettes about ne’er-do-wells getting locked away for gambling and over-the-top partying. In 1955, Webb Pierce‘s version of the song stayed No. 1 on the country chart for 21 weeks. Following the success of “Jailhouse,” Rodgers wrote and recorded a follow-up tune, “In the Jailhouse Now No. 2.” Alas, it did not improve on the original or vary significantly from it.

“Folsom Prison Blues,” Johnny Cash (1955)
Since this song is more popular than “Happy Birthday,” it needs neither introduction nor explanation. Still, it’s worth remembering that the prisoner in question “shot a man in Reno just to watch him die” and is now paying big time for this grotesque form of amusement. “When I hear that whistle blowin’,” he moans, “I hang my head and cry.”

“Some Old Day,” Flatt & Scruggs (1957)
“I’ve been workin’ out in the rain/Tied to the dirty old ball and chain.” So begins this story in which a convict apologizes to his mother for his cruelties and transgressions and promises her that “some old day” he’ll be free of “this dirty old calaboose.” Somehow, we’re not convinced.

“Stone Walls and Steel Bars,” the Stanley Brothers (1963)
This convict summarizes his crime succinctly: “Jealousy has took my young life/All for the love of another man’s wife.” So here he is in Alcatraz, about to take his last walk, after which, he says, there’ll be “no more stone walls and steel bars and you on my mind.” His sense of relief is palpable.

“Blackjack County Chain,” Willie Nelson (1967)
In this tale, a brutal sheriff picks up vagrants and enslaves them on his road-building gang. “All we had to eat was bread and water/Each day we had to build that road a mile and a quarter/Blacksnake whips would cut our backs when some poor fool complained/But we couldn’t fight back wearin’ 35 pounds of Blackjack County chain.” However, they do fight back when they catch the sheriff napping. And guess what they use to beat him to death with?

“Sing Me Back Home,” Merle Haggard (1967)
Only a rabid death penalty advocate can listen to these lyrics without shedding a tear. As the condemned man is walked toward the execution chamber, he asks that his “guitar playing friend” be allowed to “sing me back home with a song I used to hear/Make my old memories come alive/Take me away and turn back the years/sing me back home before I die.” There are no references to the man’s crime — just this eloquent nod to the power of music.

“A Week in a County Jail,” Tom T. Hall (1969)
Picked up for speeding, the culprit here is confined to jail until a judge comes around. In the meantime, he has to adjust his tastes to make “hot bologna, eggs and gravy” palatable and the jailer’s homely wife desirable, both of which he does before going jauntily on his way. This was Hall’s first No. 1.

“I’ll Break Out Again Tonight,” Merle Haggard (1974)
If I were on the parole board, I’d give this guy a break. As boredom presses down on him and night approaches, he can finally escape — via his imagination. “These walls and bars can’t hold a dreamin’ man/So I’ll be home to tuck the babies in/They can chain my body but not my mind/And I’ll break out again tonight.” That mention of babies just tears me up.

“11 Months and 29 Days,” Johnny Paycheck (1976)
This bozo doesn’t know exactly what got him into the “slammer,” but he’s reasonably certain he’d rather be somewhere else. And he’s damn sure he wants everyone to “keep your hands off my woman, I ain’t gonna be gone that long.” Jeez! Eleven months and 29 days! That’ll seem like a year.

“There Ain’t No Good Chain Gang,” Waylon Jennings and Johnny Cash (1978)
Here we have a sarcastically reassuring note from the jailbird to the folks back home, letting his mama and papa know he’s learning a lot in the lockup: “Things like there ain’t no good in an evil-hearted woman/And I ain’t cut out to be no Jesse James/And you don’t go writin’ hot checks down in Mississippi/And there ain’t no good chain gang.” Ah, education. It’s something they can’t away from you.

“Ol’ Red,” Blake Shelton (2002)
Being sentenced to 99 years kind of troubles your mind, especially when it’s the upshot of having found your wife in flagrante Dixie with another man. But two years in, our boy becomes a trustee and is put in charge of caring for Ol’ Red, the convict-sniffing hound from which there is no escape. Having had firsthand experience with the power of animal attraction, the trustee smuggles in a female dog — and you know the rest. As the last line of the song says, “Love got me in here, and love got me out.” Prison’s a bitch, ain’t it?