John Prine

The Best John Prine Songs

December 2, 2021 2:00 pm GMT
Last Edited June 16, 2023 9:26 am GMT

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When John Prine died in 2020, it seemed like the whole world burst into tears. The news of his passing triggered an outpouring of love and respect that was in equal parts heartfelt and phenomenal.

His music had touched the souls of all who heard it – transcending the borders of the generations and the genres.

He told the truth as he saw it with tender wisdom - combining honesty, compassion, empathy and homespun humour. He was incredibly endearing and totally unique.

Here are some songs that have helped see me though the past 50 years:

Atlantic Records | 1972

Illegal Smile

The release of his first album ‘John Prine’ in 1971 coincided approximately with my debut as presenter of the TV music show ‘Old Grey Whistle Test’, and we featured his music on the show many times. It’s incredible to think that the album wasn't a commercial success when it first came out, despite the wealth of material on board.

This is the opening track and the first song of John’s I ever heard. He told me that it wasn’t about smoking dope, more about his childhood tendency to smile at things the rest of the world couldn’t see. Either way, the lyrics still make me chuckle.

Oh Boy | 2018

When I GetTo Heaven

The release of ‘The Tree of Forgiveness’ in 2018 ensured that John’s career would end on an all-time high. Produced at the historic RCA Studio A in Nashville by Dave Cobb, It proved to be the fastest selling album of his entire career, winning three Grammy nominations and Album of the Year at the Americana Music Association Awards.

The lyrics of this song ("Check into a swell hotel, ain’t the afterlife grand") couldn't have been more apt, because John’s wife Fiona had booked him long-stay into the Omni Hotel in Nashville so that he could concentrate on bringing the lyrics of the record to life.

"She knows that after so many years on the road, I function better in a hotel", he said when the album was released. "That way, if I wanted to write at 3 in the morning or 3 in the afternoon I could. There was no pressure". The result was a collection of some of the best songs of his career.

Oh Boy | 2005

Glory Of True Love

To my mind, if ever a song defines John’s warm, rolling, idiosyncratic, unselfconscious style it is this one. Released as the opening track of the fabulous Fair and Square album in 2005, it has good vibes to spare. "Oh the glory of true love, it’s a wild and precious thing / It don’t grow on old magnolias, or only blossom in the spring". True poetry.

Oh Boy | 1988

Sam Stone

In his pre-performer days of the mid-60’s, John had been drafted into the American army and stationed in Germany. Although he never served in the Vietnam war, he could empathise with the boot camp buddies who returned from the killing fields broken and traumatised by their experiences on the front line. Few recognised their condition as PTSD at the time, but John Prine could feel their pain. This is their song.

Oh Boy | 1995

Lake Marie

This track, included on the Grammy nominated 1995 album Lost Dogs and Mixed Blessings, represents the lyrical convergence of several themes going on in John’s head – a crime scene, a crumbling marriage and the push and pull of struggle and heartache. It’s probably the best-known cut on this big-production record and is also Bob Dylan’s favourite John Prine song.

Oh Boy | 1995

Same Thing Happened To Me

I really love this song.It’s another from the Lost Dogs and Mixed Blessings album, but in contrast to the intensity of ‘Lake Marie’, it has a light J.J. Cale-style groove that made it a most unlikely line-dance sensation (John Prine? Line dancing?? I know! Check YouTube!!).

The imagery of the lyric is once again extraordinary - "Moonlight shining on the back of my hand / Cat fight rattlin’ the garbage can" - representing John at his endearingly eccentric best.

Oh Boy Records | 1991

All The Best

‘All The Best’ was part of the Grammy-winning The Missing Years album, released in 1991 when I was the DJ on the Midnight to Morning Show on Radio 1. I played this wish-you-well song multiple times on that programme, often matching it with John Martyn’s ‘May You Never’ because of the similarity of sentiment.

The album is a blockbuster. Recorded mostly in Los Angeles, the studio musicians include Tom Petty, Benmont Tench and Mike Campbell from the Heartbreakers, Albert Lee, Phil Everly, Bonnie Raitt…oh, and Bruce Springsteen on backing vocals.

Oh Boy | 2016

My Happiness

This is a truly beautiful version of an American classic. ‘My Happiness’ was originally recorded in the late 1940’s by everyone from Bing Crosby to Perry Como, but this tender interpretation by John and his wife Fiona Prine, enriched the glorious For Better, Or Worse in 2016, an album that features a collection of duets John recorded with his favourite female singers, including collaborations with Holly Williams, Morgane Stapleton, Kacey Musgraves, Lee Ann Womack and his soul sister Iris DeMent.

Oh Boy | 2000

Angel From Montgomery

Regarded by many as John’s signature song, ‘Angel From Montgomery’ expresses many shades of love, longing and regret. Recorded in Memphis in 1970, it was featured on John’s self-titled debut release – a record that immediately forged his reputation as a truly great writer - and again on his Souvenirs album. The song has subsequently been covered multiple times by an array of world class artists including Dave Matthews, Tayna Tucker, Ben Harper, Maren Morris and definitively by Bonnie Raitt, who popularised it on her Streetlights album in 1974.

Oh Boy | 2020

I Remember Everything

My No.1 John Prine song is the last one he ever recorded; produced at the RCA studio in Nashville with haunting simplicity by master producer Dave Cobb – just voice and guitar.

John is lyrically leafing through snapshots of his life, contentedly reflecting the images and memories with meticulous attention, charm and significance, capturing tiny details, from blades of grass to pools of butterflies and out of tune guitars. Unvarnished and atmospheric, it stands as the perfect expression of John’s life as a singer, writer, family man and poet and stands as the perfect goodbye from one of the great artists of our time.

Subscribe and listen to Holler's The Best John Prine Songs playlist below.

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For more on John Prine, see below:

Written by Bob Harris
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