Top 10 John Prine Songs

Photo: Yellowstone National Park, YPF/Matt Ludin, Public domain, via Wikimedia Commons

John Prine spent decades writing unusual songs with a lot of humor, a dash of pain, and a whole heaping helping of insight into human nature. He collaborated with many musicians, including Phil Spector, Steve Goodman, Roger Cook, and Iris Dement, but mainly wrote his own songs. Some of his songs became hits for other artists. Ain’t that always the way?

He did manage to get a hit album with The Tree of Forgiveness in 2018, a mere 47 years after his first. John Prine was beloved by many. He even had his own label, Oh Boy Records. COVID-19 claimed millions of victims. One of those was the acclaimed Grammy Award-winning genre-crossing singer and songwriter John Prine, who died at the age of 73. Do your ears (and heart) a favor by listening to these top 10 John Prine songs.

#10 – Illegal Smile

This is the first song on John Prine’s first album, 1971’s John Prine. The album would only peak at 154 on the charts, but it later got on almost everyone’s list of albums you need to hear before you die. Listen to this if you don’t have time for the whole album. “Illegal Smile” shows that John Prine was a different kind of songwriter with “Bowl of oatmeal tried to stare me down, and won.” Not only could he write a catchy tune, but he had a sense of humor. There are some delightful rhymes at the end. John Prine would later insist that the song was not about marijuana use but about how he could find something to smile about that no one else could smile about.

#9 – Grandpa Was a Carpenter

John Prine has said that even as a child, he always liked old people. This might be because of his grandfather. His grandfather was a musician, while his father was a tool-and-dye maker. Whether the song is about his grandfather is not the point. The point is that it’s a vivid portrait in song of the strange little details that make up a person’s life. For example, Grandpa “voted for Eisenhower ‘cause Lincoln won the War.” There are stranger reasons why people vote the way they do. There’s also a telling detail of the church, with “hearing aids in every pew.” This song originally appeared in the 1973 album Sweet Revenge and was rerecorded for his 2000 album Souvenirs.

#8 – Fish and Whistle

This almost chipper song has a lively melody and a wry look at life and the afterlife. He seems to talk to God and the listener, saying, “You forgive us, and we’ll forgive You/ We’ll forgive each other until we both turn blue.” He sings about getting a job scrubbing parking lots at only fifty cents an hour. To echo the title, there is a recorder or tin whistle doing cartwheels around the melody and lyrics. This came out in 1978 on Bruised Orange and was rerecorded for Souvenirs.

#7 – In Spite of Ourselves

This duet with Iris Dement is a funny look at a couple that sees the best and worst of each other. This is perhaps one of the only songs you’ll hear that mentions somebody sniffing underwear. It has touches of sweetness without becoming saccharine. John Prine was Iris Dement’s mentor. She called him one of the best songwriters ever because he could find nobility in each person. Oscar-winning actor Billy Bob Thornton commissioned the song for the critically acclaimed 2001 movie Daddy and Them. John Prine even had a role in the film as brother to Billy Bob Thornton’s character. This can be found on the 1999 album of the same title.

#6 – When I Get to Heaven

This song was written for John Prine’s last album, The Tree of Forgiveness (2018), which would be the name of the club he wanted to open up in Heaven. Producer John Cobb recalled that John Prine suggested adding kazoos, which would complete the song and make people laugh. And it did. The song also features laughter from his grandson. It is about the only song you’ll ever hear with the phrase “syphilitic parasitics.” It makes you hope that this was the heaven that John Prine is in now, smoking a cigarette “nine miles long.”

#5 – Hello in There

Many John Prine songs are about old people. Songs about them, like this one, appeared even on his 1971 debut album. This is a poignant, touching, and, at times, painful look at an elderly man telling you about his current life. “The news just repeats itself,” and his wife just stares out the back door screen.” John Prine explained that the song’s echo was inspired by the Beatles’ “Across the Universe.” In this song, old trees grow stronger, old rivers grow wild, but old people? Well, they grow lonely. This was yet another song John Prine re-recorded for his 2000 album Souvenirs.

#4 – Some Humans Ain’t Human

The title tells what this country folk-flavored song is about. It’s gentle and sad with a simple, elegant arrangement. Although he does seem to heave a metaphorical sigh at the cruelty of people, he hasn’t entirely given up. He tries to shed light on the darkness of people (and one President in particular) to effect change. The song does feature his usual quirky sense of humor, such as describing cruel people as “ice cubes with hair.” Released on the 2005 album Fair & Square, it sadly sounds like it will be pertinent for centuries to come.

#3 – That’s the Way That the World Goes Round

This song was covered by Miranda Lambert in 2009, but arguably John Prine’s original was better. This version features recorders, which are not common enough in country or even folk music. John Prine would say of this song that he was “fed up” with cynicism and wanted to write it from a child’s point of view. Somehow, it seems more unique to John Prine’s point of view than that of a child, especially since the song mentions domestic abuse and nearly freezing to death in a bathtub. Either that or John Prine’s childhood was one of a kind. This appears on the 1978 album Bruised Orange.

#2 – Sam Stone

Many of the songs on this list are funny. That’s not to say that John Prine only wrote funny songs. It’s just that funny songs are much harder to write than sad ones. This is a bittersweet song about a fictional ex-Vietnam vet. John Prine would explain that Sam Stone was a compilation of many Vietnam vets he knew. He noticed that all of the anti-war songs he heard didn’t talk about the soldiers, so he wanted to fix that. And did. The song gives a series of gut-punches, emphasizing, “Jesus Christ died for nothing, I suppose.” “Sam Stone” originally appeared on John Prine’s eponymous 1971 debut album, but he rerecorded it for his 2000 album Souvenirs.

#1 – Dear Abby

John Prine gives a lot of advice in his songs. So, it’s only natural that he would write a song about the Queen of Advice, Dear Abby. (If you have no idea who Dear Abby was, do a quick Google search now. We’ll wait — okay. Welcome back.) Writing anything more about the song will give the joke away. Just click the link and listen, and then you’ll know why it made the top of our list of best John Prine songs. The original version appeared on the 1973 album Sweet Revenge.