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 major hit album with The Tree of Forgiveness in 2018, a mere 47 years after his first. The album debuted at number five on the Billboard 200, the highest chart position of his career. John Prine was beloved by many. He even had his own label, Oh Boy Records. Prine died on April 7, 2020, at the age of 73 from complications of COVID-19. His career ultimately brought him four Grammy Awards, including two posthumous wins for “I Remember Everything.” Do your ears and your 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 landed on countless lists 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 the line about a bowl of oatmeal staring him down and winning. 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 really 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 often wrote about older people with an unusual amount of empathy for a songwriter who was still young himself. “Grandpa Was a Carpenter” turns a collection of odd little details into a vivid portrait of a man’s life. Grandpa voted for Eisenhower because Lincoln won the war, and there are hearing aids in every pew at church. Those details are exactly what make the song feel so alive. It originally appeared on the 1973 album Sweet Revenge and was rerecorded for Prine’s 2000 album Souvenirs.

#8 – Fish and Whistle

This almost chipper song has a lively melody and a wry look at life and the afterlife. Prine seems to talk to God and the listener about forgiveness while casually wandering through the everyday absurdities of life. He sings about getting a job scrubbing parking lots at only fifty cents an hour. To echo the title, a recorder or tin whistle does cartwheels around the melody and lyrics. The song 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 who see 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 an important mentor and friend to Iris DeMent. The song was written after Billy Bob Thornton and Marty Stuart asked Prine for a song for the film Daddy and Them. It first appeared on Prine’s 1999 album In Spite of Ourselves, before the film reached audiences.

#6 – When I Get to Heaven

This song was written for John Prine’s final studio album, The Tree of Forgiveness (2018). Producer Dave Cobb recalled that Prine suggested adding kazoos, helping complete the song with exactly the kind of oddball touch that made people laugh. The recording also includes the sounds of family and laughter in the background. It is about the only song you’ll ever hear with the phrase “syphilitic parasitics.” It makes you hope that this was the heaven John Prine found, complete with a vodka and ginger ale and a cigarette nine miles long.

#5 – Hello in There

Many John Prine songs are about old people. Songs 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 sits staring through the back door screen. In this song, old trees grow stronger and old rivers grow wilder, but old people grow lonely. It became one of Prine’s signature compositions and was another song he rerecorded 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 Prine seems 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 American 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

Miranda Lambert covered this song 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. Prine described wanting to move away from easy cynicism and find a simpler point of view. Somehow, it still seems uniquely John Prine, especially since the song touches on domestic misery and nearly freezing to death in a bathtub while somehow remaining funny. 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 devastating song about a fictional Vietnam veteran. Prine explained that Sam Stone was built from observations of veterans he knew. He noticed that many anti-war songs did not really talk about what happened to the soldiers who came home, so he wanted to write about that side of the story. And he did. “Sam Stone” originally appeared on John Prine’s eponymous 1971 debut album, and 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.