In the olden days, a record label would spend thousands, if not millions, of their local currency to promote a new act. They would fund a radio tour, a support slot, an EP or album and a headline tour, and if it didn’t work they were expendable and were tossed aside.
Nowadays, the act has to do most of the legwork to even think about a label coming to their aid. Amazingly, Charley Crockett seems to have cracked the code for how to become a roots star. Rule one: no compromising. It worked for Jason Isbell, Steve Earle, Waylon Jennings and Hank Williams, in reverse order, and it sure works in an era dominated by TikTok and hip-hop. Crockett is now signed to Island Records, who have promised him total creative control of his work.
Rule two is that the song comes first, closely followed by rule three, the songs come often. As you may know, Crockett is relatively prolific, with the regularity of releases reminding me of Brian Wilson, Elton John and Stevie Wonder, who all hit golden patches between 1960 and 1980 when the record business needed new product on a regular basis. By the time Prince wanted to do the same in the late 1980s, with the benefit of his own studio complex where he and his various bands and projects came together seven days a week, his label tried to hold him back. Crockett would certainly have made Prince very jealous.
On my closest available streaming service, there are almost 250 pieces of music on various releases by Crockett; this would take half a day to listen to, were I to gulp them all down in one go. I’ll pick one in 25 of them for this Essentials feature, some of which will be known to many fans; I implore another writer to dive deeper into Crockett’s work, or look at songs of other writers he has interpreted.
Because ranking songs is the errand of a fool, I will use the numbered countdown merely as a way to go back in time from the most recent to the oldest in Crockett’s catalogue.
Number 10: ‘Lonesome Drifter’ from “Lonesome Drifter” (2025)
In a piece by Josh Crutchmer for Rolling Stone, Crockett calls himself “a cowboy singer”, one who finds himself in the lineage of Jack Clement and Waylon Jennings; he is guided by the latter’s credo of writing songs in ten minutes but taking ten years to think them up. It must be astonishing for him to be working with Waylon’s son Shooter on his recent album Lonesome Drifter.
Guy Lincoln reviewed it when it came out a few weeks ago, and every word he writes is true. The title track, which opens the album, should be synced as quickly as possible to one of those TV shows set on or near the kind of “lonely highway” Crockett sings of here. The director could add panning shots of “cotton fields” and a “nine-pound hammer” to match up with the lyrics, which Crockett delivers like a man who has been a professional songwriter and performer for a decade now.
The long, chunky guitar coda that closes the track could be turned into a jam onstage. The track is hypnotic without putting you to sleep and a fine place for people somehow still unaware of Crockett to start.
Number 9: ‘How Low Can You Go’ from “Visions of Dallas”(2024)
Crockett sang the title theme to the Martin Scorsese movie ‘Killers of the Flower Moon’, and he included the song on his album “Visions of Dallas” Also nestled on that album is ‘How Low Can You Go’, the album’s most immediate track thanks to its sultry groove and liquid guitar line.
“Baby, you just tear me apart”, sings the downtrodden narrator, before he is joined by a magnificent piano line that doesn’t sound much like he’s being torn apart; there’s even a fadeout, something of an endangered species these days. If Chris Stapleton, Scotty McCreery or Zach Top cut this song, it would be an enormous hit.
Number 8: ‘$10 Cowboy’ from “$10 Cowboy” (2024)
In that Rolling Stone piece, we learn a little about our hero: born in San Benito on the Texas-Mexico border, Crockett was raised by his mum in a trailer park, beginning to busk around first the USA and then Europe, before he returned to Texas and became friends with Leon Bridges. This explains the pair’s somewhat odd co-headline tour later in 2025, and their shared love of putting their voice through vintage microphones, or at least treating them with echo.
The rootsy feel of this song, the opening track from the parent album of the same name, matches its lyric. The main point of interest comes in the delivery of the line “he looks a lot like me”, where Crockett pauses briefly in his delivery and adds a fifth beat into a song that is otherwise in straight 4/4 time.
“Ten dollars was a whole lot of money”, Crockett intones over the song’s outro, recalling the days when people would ask him if he rode bulls too. He also references Billy McClain, a black actor from the early days of the motion picture who played acrobats and “fell off a time or two”; thus is being a singer an equally “hazardous occupation”.
Number 7: ‘Ain’t Done Losing Yet’ from “$10 Cowboy” (2024)
Both this and the title track to “10 Cowboy” appeared as part of Crockett’s Houston Rodeo set, which also suggests other essential songs from his bulging catalogue.
Crockett has been in trouble with the law, committing both blue- and white-collar crime, so he has done a whole lotta losin’ in his life so far. One of the biggest wins came in March 2025, when he played to over 50,000 people at the Rodeo; coupled with a network TV performance on The Tonight Show in front of millions more, either live or on Youtube, Crockett is in danger of blowing his cover as a cult musician and becoming a superstar.
Crockett also made his Later… With Jools Holland debut in 2024, playing his song ‘Solitary Road’, as part of a visit to the UK to play three dates in early May at Hoxton Hall. At the show I attended, Crockett showed control of both his material and his audience, dealing with a rowdy heckler and putting across his art.
I remember this song fondly, with its hugely singable chorus which complains of “this life of trouble and regret” and verses that paint a tableau of Crockett playing a slot machine and being watched by a fellow gambler, whose catchphrase he borrows: “There’s plenty of time for hurting and I ain’t done losing yet”.
Number 6: ‘Hard Luck & Circumstances’ from “$10 Cowboy” (2024)
A third tune from ‘$10 Cowboy’, Crockett played this proper country song solo at the Hoxton Hall show, but on record his voice is surrounded by a small group of singers who emphasise how “me and trouble, we’re old friends”. Waylon Jennings could have written this and, thanks to its trebly solo, recorded it too.
Number 5: ‘I’m Just a Clown’ from “The Man from Waco” (2022)
Fred Arnold of this parish called ‘The Man from Waco’ “a contender for album of the year”. It was produced by another of the singer’s guiding star, Bruce Robison, who once called his protégé “the Adele of country music”.
Crockett himself told Josh Crutchmer, who is fast becoming the scribe of Texas and Oklahoma music, that he is “taking my brand of Texas to the world”. The track ‘Cowboy Candy’, complete with hiccupping yodel, is more memorable than ‘I’m Just a Clown’ on first listen, but this one also makes his regular setlists. It’s an extended metaphor where the guitar player compares himself to a “joker” who “turns a trick for you…better to be thought of as a fool”.
As well as the emphatic guitar solo, the rhyme scheme in the chorus is strong and sombre: “clown/frown/around”. Has Crockett been taking inspiration from ABBA, setting a wretched set of lyrics to an arrangement that misdirects the listener, complete with a small horn section and tambourines on the backbeat? “I’m so lonesome I should charge a fee!” he moans in the final verse, less cowboy than soul man.
Number 4: ‘Are We Lonesome Yet’ from “Music City USA” (2021)
Country music is, as Brad Paisley once sang, “your life in a song”, and here’s one torn from the pages of the book of Crockett. He heads to New York and its many delights: “a champagne room”, “chandelier”, “electric billboards”, and “the mezzanine up the staircase, past the ice machine”.
Over three familiar chords, with faint fiddle in the mix and useful contributions from a pedal steel, a subdued Crockett sings of there being “a price to pay” to be in the room with the movers and shakers who are “judging me in jest”; “it costs a lot more to stay; nobody wants to share”. Here’s a solo version of the song, recorded in Texas for Paste Magazine, which mimics the busking Crockett used to do before he started playing arenas in Houston and small halls in Hoxton.
Number 3: ‘Music City USA’ from “Music City USA” (2021)
The title track of ‘Music City USA’ begins with a blast of pedal steel that you could hear on a country song from 1972; ditto the chorus of backing vocalists who caress his complaints. We find our picaresque narrator heading to the home of commercial country music. It turns out Crockett “shouldn’t have come” to Nashville either, “cos folks in here don’t like my kind”.
In the second verse he sings of all the places he could “draw a line from Texas” and head to, be it California, Georgia, Alabama or New York City, but he would still meet malice. He coats the line “they’ve got a lot to say in Music City USA” with a sweet melody that suggests he doesn’t need them just as much as they don’t need him either. “How would you like to pay my dues?” he asks an unnamed person, aware that to succeed means to suffer. If that’s what it takes, Crockett suggests, he has no wish to be “in the alley with the ghosts”.
Number 2: ‘Welcome to Hard Times’ from “Welcome to Hard Times” (2020)
In between this album and ‘Music City USA’, Crockett recorded an album in tribute to James “Slim” Hand, a songwriter’s songwriter, which gives his fans some idea of the kind of artist he wants to be.
The title track of the album “Welcome to Hard Times” also made the Houston Rodeo setlist, where the singer told the crowd: “This half of the room says Charley Crockett is too country, and this half of the room says Charley Crockett isn’t country enough!” This may be a pose – country is whatever people say it is – but Crockett has followed Jennings in following his muse and building his fanbase one fan at a time.
His music is in opposition to whatever is making money for the executives on Music Row. “Life’s a casino,” he sings in the first verse; “the dice are loaded and everything’s fixed”. Picking up on the theme of ‘Ain’t Done Losing Yet’, he asks his listener if they “like sinning…you will before you go”, recommending that they take a turn with “the bright blinking lights” which, it appears, he is enduring in life’s casino.
As is often the case in his music, Crockett asks direct questions of the listener and orders them to “take a look in my eyes, tell me what you see”.
Number 1: ‘I Am Not Afraid’ from “In the Night” (2016)
For the first time on this list, Crockett is in love, addressing his “sugar, honey pie…lil girl” over pedal steel and egg shaker percussion. His vocal is less cowboy and soul man and more teen-pop singer from 1958: “Look into my eyes and see this love so that you’ll always know”.
The Spotify numbers never lie, though: this is by far and away Crockett’s most popular song, and the oldest in this Essential selection, which cannot begin to cover in any depth the 250 songs Crockett has recorded across the last ten years. In that single decade, Crockett has grown from promising busker to pivotal figure of the Texan musical firmament. Naturally, he’s probably sitting on dozens of songs that will knock out any or all of these songs from his Essential ten.
I daresay another writer would pick ten entirely different songs, to which I say: what’s stopping you?
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