John Prine's 10 Best Songs: Critic's Picks

There is a definite warmth to the music of John Prine. As a songwriter, he has notched hits from the likes of Country Music Hall of Fame members such as George Strait and Don Williams, but he's just as effective – even more so – when he's recording his own words.

The gritty realism of what Prine brings to the table sometimes requires a second listen to be able to fully comprehend the message of the song – and sometimes, even then, it might be cloudy.  But, at the very least you will smile and nod your head in agreement. And, you just might be the better for hearing one of his classic songs – just like Bonnie Raitt was in 1974. More on that one later! Here are ten John Prine song moments that stand with his best!

Best Songs: Alabama | Alan Jackson | Alison Krauss | Billy Currington | Blake Shelton | Brad Paisley | Brett Eldredge | Brett Young | Brooks & DunnCarrie Underwood | Chris Stapleton | Clint Black | Conway Twitty | Cole Swindell | Darius Rucker | David Allen CoeDierks Bentley | Dixie Chicks | Dolly Parton | Dwight Yoakam | Eric Church | Faith Hill | Garth Brooks | Gary AllanGeorge Jones | George Strait | Glen Campbell | Hank Williams Jr. | Jason Aldean | Johnny Cash | John Denver | Justin Moore | Keith Urban | Keith Whitley | Kelsea Ballerini | Kenny Chesney | Kenny Rogers | Lady Antebellum | Little Big TownMartina McBride | Merle Haggard | Miranda Lambert | Patsy Cline | Randy Travis | Rascal Flatts | Reba McEntire | Sam Hunt | Shania Twain | Sheryl Crow | Thomas Rhett | Tim McGraw | Toby Keith | Travis Tritt | Vince Gill | Waylon Jennings | Willie Nelson | Zac Brown Band

10. John Prine – “Please Don’t Bury Me”

Only John Prine - with his laid-back style and personality - could made this timeless evergreen about a man’s final moments - and his last instructions - sound in any way like a beautiful or funny way to go. But, alas, that is the magic of John Prine. He can make you think, as well as smile all in the same lane.

9. John Prine – “ Six O’Clock News”

In interviews over the years, Prine said he penned this song about a kid who lived in the neighborhood close to him growing up, and stayed in quite a bit of trouble. As it turns out, his fate was sealed from conception, as the vague lyrics seem to reveal. Interpretation is up to the listener wiht this chilling John Prine song, but the moral of the story is that life isn’t always beautiful, to quote the Country hit from Gary Allan.

8. John Prine –“Illegal Smile”

The consensus among Prine’s devoted fan following is that this song is about drugs. In interviews, Prine has acknowledged those thoughts, but said that to him it was totally representative of the fact that he found humor in what other people sometimes didn’t. Whether fans bought his explanation, the composition remains a favorite in his extensive catalog.

7. John Prine – “Grandpa Was A Carpenter”

This track from his 1973 Sweet Revenge album ranks among the most sentimental of his career. He evokes a time gone by when he speaks of his grandfather with reverence and love. Prine later covered the song with the Nitty Gritty Dirt Band on the 1989 collection Will The Circle Be Unbroken, Volume 2.

6. John Prine – “That’s The Way The World Goes ‘Round” 

Prine recorded this song originally in 1978 for his excellent Bruised Orange disc. One fan who was touched by the song’s lyrics wasn’t even born yet. Her name is Miranda Lambert, who recorded a rockin’ version of the song in 2009 for her award-winning Revolution album.

5. John Prine – “Your Flag Decal Won’t Get You Into Heaven Anymore”

This track from his 1971 debut album still evokes much passion on both sides of the political coin nearly five decades after its’ original release. His more conservative fan base will sometimes walk out of performances when he does this Vietnam protest number, while many have cheered in agreement over the years. The song certainly took on new meaning in the 2000s, with the war in Iraq. Whether you stand with the right or the left, if the true mark of a writer is to pen a song that touches a nerve - he did just that with this essential entry into the John Prine song catalog.

4. John Prine – “Sam Stone”

This song follows the tragic story of what happens to a soldier once he makes it home to American soil. Originally titled “Great Society Conflict Veteran’s Blues,” this song never mentions the Vietnam war by name, but the timing of this 1971 recording was right in line with the height of the War. Many who survived the battle still found themselves scarred when they returned to American soil, and some turned to various means to get through the moment. Some survived....others didn’t.

3. John Prine – “Speed Of The Sound Of Loneliness”

One of the most-recorded songs in the John Prine universe is this moody track, which was originally cut on his 1986 album German Afternoons. In 1993, Nanci Griffith recorded a version for her Other Voices, Other Rooms disc that included Prine as a guest vocalist, and the song was also recorded by Kim Carnes. Still, many times, the original is sometimes the best - and that is very true here.

2. John Prine – “Angel From Montgomery”

A friend suggested that Prine write a song about the elderly. The singer-songwriter felt he had covered that base quite well in his “Hello In There.” However, as Prine worked through the creative process, he began to become drawn to this story about a woman who wanted to escape it all. Carly Simon cut the song immediately following Prine’s 1971 version, and John Denver cut the track on his 1973 disc Farewell Andromeda album. The next year, Bonnie Raitt would lift this John Prine song into the national stream of consciousness with a performance that became one for the ages.


1.John Prine – “Paradise”

Perhaps one of the greatest pieces of advice that one can give a songwriter is to write about what you know. As the lyrics of the song attest, Prine would sometimes visit the area in Kentucky where his parents were from, and would see the devastation around the Green River in Eastern Kentucky due to strip mining. Prine once remarked to Jasper Rees of that nobody was more surprised the song has become a standard in the Bluegrass community because - in his words - “I wasn't even going to record it because I didn't think anybody would be able to pronounce Muhlenberg."