Artist - Kelsey Waldon

The Best Kelsey Waldon Songs

January 30, 2023 10:57 am GMT
Last Edited June 21, 2023 1:00 pm GMT

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The pride of West Kentucky (the town of Monkey’s Eyebrow to be specific), Kelsey Waldon received a life changing boost by being mentored by John Prine who also signed her to his label Oh Boy Records.

Her clear, shimmering voice, flowing melodies and thoughtfully crafted, often socio-political lyrics over the course of four albums and some EPs make comparisons to fellow Kentuckian Loretta Lynn inevitable.

Here, Holler picks 15 of Kelsey Waldon's best songs:

Kelsey Waldon and John Prine


John Prine helped Kelsey by having her open his shows where she often joined him on this classic from his debut. They finally recorded it - audio and video - in 2019 shortly before Prine’s death. Waldon still includes it in her sets as a tribute to the iconic songwriter whose parents were also born in Western Kentucky.

Oh Boy Records marketed and distributed by Thirty Tigers | 2014


Waldon takes the voice of an immigrant protagonist in this melancholy waltz time tune, one of a handful written about the coal miners that populate the area where she grew up. The lyrics concern a laborer, working dawn to dusk, who finds it difficult to leave his dangerous profession despite having nightmares of dying in an explosion. 

Oh Boy | 2022

No Regular Dog

Producer Shooter Jennings captures Waldon’s somber, introspective, intermittently frustrating look at her career as a road weary singer songwriter on the title track of her most recent album. “Same old show, a different place, another pеrson / Just grinnin’ in your face” displays a reticence to embrace her lifestyle over a lovely yet mournful, occasionally ominous melody. 

Oh Boy Records marketed and distributed by Thirty Tigers | 2019

Kentucky, 1988

Another song about Waldon’s life growing up in the titular state. Born to “two imperfect people,” she describes the tribulations of being raised in a financially struggling family. It’s in her DNA she explains as drums thump like the heartbeat of someone determined to leave her hometown but who is also philosophically tied to it.

Oh Boy Records marketed and distributed by Thirty Tigers | 2020

Mississippi, Goddamn

Nina Simone’s incisive protest song, one of seven terrific covers Waldon recorded for an EP released during the pandemic, includes the talents of Americana women Adia Victoria and Kyshona Armstrong. They swap verses on this riveting performance decrying the oppression and racism of Southern US states - specifically Mississippi, Alabama and Tennessee - with chilling, menacing acoustic accompaniment.

Oh Boy Records marketed and distributed by Thirty Tigers | 2020


Waldon takes Neil Young’s 1970 politically searing discourse about the Kent State student killings at the hands of the National Guard and adds punches of taut pedal steel and edgy lead guitar, bringing a dark country reading to the folk-rock classic. It’s another rugged, clinched fist cover from 2020’s They’ll Never Keep Us Down EP.

Kelsey Waldon

Rex's Blues

Never on an official Waldon album, this 2012 live track takes on Townes Van Zandt with just an acoustic guitar and Brett Resnick’s pedal steel. The darkly moving piece reflects on how life, and possibility drug addiction, leaves you “alone and low as low can be.”

Oh Boy Records marketed and distributed by Thirty Tigers | 2019


This demonstration of resilience in the face of life’s turbulence clearly resonated with Waldon’s audience who made it one of her most streamed songs. “Even if the world crumbles at your feet / You’re gonna hold up that earth somehow,” she sings with the mixture of toughness, vulnerability and intensity that defines much of her work.

Oh Boy | 2022

Simple As Love

Waldon doesn’t write much about romance, but this sweet ballad, focusing on the power of love, is one of the highlights from 2022’s No Regular Dog. “Your love brings out the best in me” isn’t a radical concept, but her laconic phrasing about the powerful attraction to her lover is delivered with deeply felt sincerity.

Oh Boy Records marketed and distributed by Thirty Tigers | 2019

Dirty Old Town

The only jaunty honky-tonking two-stepper in Waldon’s catalog is a defiant treatise against getting sucked into the depths of people and a town enticing the singer into a darker side, which she feels strong enough to reject. It’s a serious concept… but you can dance to it.

Oh Boy | 2022

Backwater Blues

This slower tune, “Dedicated to the Resilience of Kentuckians” as its video states, features fiddle which harness the bluegrass underlying much of Waldon’s music. It tells of how climate, with its floods and droughts, creates life challenges for those in her home state, singing “You wouldn’t know mother nature’s power if she never made a sound”.

Oh Boy Records marketed and distributed by Thirty Tigers | 2019

Sunday's Children

Funk is not a style we associate with Kelsey Waldon, but the opening bass line of this 2019 screed against organized religion tainting the minds of the young sounds like a lost Motown riff. The stripped down instrumentation, including sharp shards of pedal steel, focuses on lyrics decrying the Sunday school indoctrination of kids and the lies they are told in the guise of faith. 

Oh Boy Records marketed and distributed by Thirty Tigers | 2022

Sweet Little Girl

A slice-of-life story of a simple girl who lost her way has bits of Waldon’s own struggles with addiction woven through the lyrics. The most streamed entry from her latest album shows that the narrative resonates for many listeners who understand the need to get high just to make the time pass.

Oh Boy Records marketed and distributed by Thirty Tigers | 2022

Tall and Mighty

The finest track from Waldon’s No Regular Dog is also one of the best she has penned. It’s an exploration of the conflicting feelings concerning her career of “trying to live up to some honky tonk dream”. The closing “Everything’s going to be alright / you just can’t stand tall and mighty all the time” partially reconciles those uncertainties but the memorable melody and catchy chorus makes it clear she has chosen well.

Monkey's Eyebrow Recordings | 2016

All By Myself

Waldon’s most streamed song by far (with over a million logged on Spotify) is a testament to copying anyone else. “If you ain’t your man, you’re nobody’s man” she asserts with swaggering confidence over simple country bass and moaning pedal steel, declaring her individualism and originality in her field.


Check out our Holler playlist of the Best Kelsey Waldon Songs below:


For more on Kelsey Waldon, see below:

Written by Hal Horowitz
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