Somebody once told Erin Enderlin that she wrote sad bastard country music. She was delighted. There’s a Felice Brothers song with the lines “I put some whiskey in my whiskey/ I put some heartache into my heart”. Enderlin pours whiskey and heartache (bars and cowboys) into her songwriting in no short measures. If those barrooms still had old fashioned jukeboxes, you’d be hard pushed to load them with sadder songs. Merle Haggard said Erin was way above average. Not over generous with the praise was Merle. Average sits drinking alone in the next town when it comes to Erin Enderlin. Her songs are gloriously sad (sad to make you feel good) and almost always with a dignified twist of defiance. Sad songs, usually from the female perspective, stuffed with backsliders, cheaters, lovers and victims… all with that golden-era country sound. Nothing does mournful like pedal steel and some fiddle. You want to sample these tracks in moderation. This feature comes with a “listen and watch responsibly” label. Enderlin can always be relied on to make an outstanding video to accompany a song’s narrative. Think Flannery O’Connor meets Edward Hopper.
Erin Enderlin is country. Maybe too country for some. She remembers taking a Conway Twitty album to Kindergarten for show and tell, asked Little Jimmy Dickens to sign her guitar at the Opry and studied at Middle Tennessee State University with the sole intention of becoming a songwriter. Enderlin didn’t hang about. Before graduating Alan Jackson cut one of her songs, then Randy Travis, followed by Lee Ann Womack and Luke Bryan. RCA offered her a development deal. Time away from performing saw Enderlin working at the Grand Ole Opry as a hostess and museum guide. Ironically, she would make her own Opry debut in 2013 and much later feature in a museum exhibition which paired established artists with rising stars. Enderlin was paired with Reba McEntire. Her first album ‘I Let Her Talk’ was released in 2013 followed by ‘Whiskeytown Crier’ in 2017. She released a quartet of EPs in 2019 that recycled some tracks from ‘Whiskeytown Crier’. The tracks on those EPs would get reacquainted on the ‘Faulkner County’ album released that same year and produced by Jamey Johnson and Jim “Moose” Brown. A greatest hits album of sad bastard country music. Heavyweight Harmonies from Jon Randall, Cody Jinks, Terri Clark, Vince Gill and Alison Krauss no less. The mournfulness did seem to peak about 2019. I’m less familiar with the tracks on the ‘Barroom Mirrors’ EP released in 2021 that became part of her album released in 2023. But this is great.
Indeed, if I’ve missed out a belter from her songwriting catalogue that you think should be here… please comment. So, not an increasing scale of heartache or alcohol by volume. Subjective to be sure… what about kinda’ chronologically sad?
Number 10: ‘I Let Her Talk’ (2013)
Running parallel to ‘Jolene’ or Cam’s ‘Diane’ this is the title track from Enderlin’s first album. The classic Erin Enderlin sound, effortless voice and guitar playing accompanied by fiddle and steel. With the great line “…a careless drunk will show you pictures too”. That ain’t no alka-seltzer going in that glass on the bedside table. Some cowboy still out there with his tail between his legs.
Number 9: ‘Ain’t It Just Like a Cowboy’ (2017)
From the album ‘Whiskeytown Crier’. Achingly beautiful. Such sadness in those crushing lines: “There’s something in those motel rooms he just can’t find with me/ Here’s the part where drinkin’ is easier than thinkin’/ About what he’s doing tonight/ He’s holding her like he held me/ God I should know better than to cry”. There’s a theme developing here. And the ending to this video is just…
Number 8: ‘Broken’ (2017)
There’s an opening line… and that lap steel just dumps burden on your heart from the beginning. Rolling Stone’s Jon Freeman beautifully described this song as a “breathtaking. empathetic tale of teenage pregnancy aimed at dispelling some of the shame around the topic”.
Number 7: ‘Till It’s Gone’ (2017)
What has the young lady done? That bottle of bourbon and pack of smokes are being heavily depleted in that motel room. “I smoked one to the filter and I watched the ashes fall/ Blew smoke rings at your memory as it danced across the wall… till it was gone”. But then you have to go on.
Number 6: ‘Tonight I Don’t Give a Damn’ (2019)
The last of the sadness trinity found on the ‘Chapter One’ EP. What an opening few lines… “Gene Watson singing ‘Farewell Party’, single barrel, double shot on ice.” What’s a one-night stand going to get you? Men, cowboys, are not put in best light in a few of these songs and videos.
Number 5: ‘Whatever Gets You Through the Night’ (2019)
Another heartbreaking song from the trinity found on the ‘Chapter Three’ EP. Sandwiched between (if this was a top twelve) ‘Sweet Emmylou‘ (she didn’t write it) and ‘Use Me Again’. A touching song that gets why people turn to anything to make them feel less lonely or keep moving through a harsh world.
Number 4: ‘I Can Be Your Whiskey’ (2019)
There’s no finer example of Erin Enderlin’s cinematic, country credentials than right here. Who is that serving behind the bar? Is there a suggestion of a happy ending? Managing to somehow match love and whiskey. “My love’s stronger than 90 proof/ Just wait and see what one kiss can do/ And if you think it’s too good to believe/ Don’t worry baby, cause this rounds on me”.
Number 3: ‘The Queen of Marina del Rey’ (2019)
Enough already. I can’t sustain the mournfulness. Name-checking Rosanne Cash and Elton John can pay dividends. Both heard and loved ‘The Queen of Marina del Rey’. It is a great song with some old-time, boozy, tack piano. Cash sent the whole ‘Faulkner County’ album to her friend Elton John. His response to Enderlin’s swagger? An invite to feature on his podcast Rocket Hour. The man’s much better at dishing out the praise than Haggard. “The album is fantastic. She’s a brand new country artist- well, new to me- that I absolutely love“. The reminiscing is cleverly done with some delicious lines such as “I was working ’til 4 at the Old Troubadour/ Pink sunglasses on like a young Elton John/ Into cocaine and boys”. Enderlin told Rolling Stone “In my mind the woman in that song is (now) a mild-mannered PTA mom and nobody knows that she has this entire other life that she lived“. “I was a sideshow sort of famous/ Called from the day I was born/ Blessed with a sick kind of strangeness/ I wore like a cheap crown of thorns” All sung with a wry smile.
Number 2: Married Young (2018)
I’ve just put this one to show how good Erin Enderlin is as a songwriter and performing live. A song she co-wrote with Alex Kline. Love the Tom Waits reference. Love this song.
Number 1: I Wrote This Song For You (2024)
The panacea to all this sadness. Signs of love’s hopeful recovery. If you’re still persevering with this countdown let’s finish in the warmth. This could be cheesy but it ain’t. The familiar sound of Trigger and the great Willie Nelson (91 no less) but he didn’t write this song for album #75… Erin Enderlin did.
What does she have to do to become a Grand Ole Opry member?
