Artist - Dylan Gossett 2

Dylan Gossett's Songs Ranked

February 13, 2024 4:19 pm GMT

email logo
link icon

Link copied

Content Sponsor

Hailing from Central Texas, Dylan Gossett makes music that’s simple, heartfelt and meaningful, with some comparing it to Zach Bryan’s honest music and thoughtful, self-written lyrics.

Gossett took over social media in 2023 with his viral song ‘Coal’, amassing nearly 100 million streams since its July release and later appearing on his debut EP, No Better Time. Before the year’s close, he signed his first record deal with Big Loud Texas/Mercury Records, etching his name on the list of next generation artists that are here to stay.

Throughout his discography, there’s a common theme of introspection and thoughtfulness. Coupled with his moving prose and heartfelt stories, Gossett’s songs are evocative and depict life’s ups and downs.

Whether it's considering our own choices, facing challenges, seeking freedom, cherishing the beautiful moments or navigating relationships, his catalog explores the complicated and uncertain aspects of the human condition.

With only seven songs released, here is Holler’s ranking of Dylan Gossett’s songs so far.

Big Loud Texas / Mercury Records | 2023

Lone Ole Cowboy

A powerful, heartbreaking song about a cowboy's life, fit with staunch emotions and vivid storytelling, ‘Lone Ole Cowboy’ shows the protagonist’s struggles with heartbreak, betrayal and the difficult life he’s lived.

The cowboy ends up confronting his problems with a gun, saying: My lady lost the love, well, I found the hate / There's a truck in the drive that belongs to another man / I've got a .45 and my finger on the band”. It’s a gripping story of a man finally pushed to his limits, yet despite it all, his strength and pride shine through, making him a captivating though tragic character.

While it contains powerful lyrics, the style is an outlier from the rest of Gossett’s repertoire. The violence and revenge plot of this gritty tale lacks his aforementioned usual theme of self-reflection.

Dylan Gossett | 2023


This is the song that helped Gossett become who he is today. Centering around the dueling concepts of love and loneliness, ‘Coal’ takes listeners through the ups and downs of relationships.

Lines like "This game of life plays heavy on my heart / and love is tough but loneliness is twice as hard" really capture the emotional weight of managing relationships and life's challenges. It's a touching song that speaks to anyone who's ever felt a longing for love and the bitter melancholy of loneliness.

While an emotional song, the lyrics as a whole don't all hold together logically. As you read through the words on paper, some of the lines don’t make much sense or convey a clear narrative. In the end, though, it almost doesn't matter as Gossett’s raw relatability cuts through any lyrical fuzziness.

Big Loud Texas / Mercury Records | 2023

Beneath Oak Trees

Staying true to yourself and finding love, that’s what ‘Beneath Oak Trees’ is all about.

Celebrating the freedom to love without fear, the line, “Cause all that matters in the end is that we're famous in this house" reminds us that being loved and accepted by those closest to us is what truly matters. Describing the beauty of nature and portraying a love that thrives under oak trees, it’s a reminder to cherish moments with a love that goes beyond the norm.

‘Beneath Oak Trees’ demonstrates some of Gossett’s most unique songwriting. His vulnerability in honoring a gentle love that can bloom away from judgment creates a tender prose, and his rare emotional directness makes this a great model of Gossett's knack for heartfelt lyricism.

Big Loud Texas / Mercury Records | 2023

No Better Time

The title track of his debut EP, this tune is about stepping out of your comfort zone and facing challenges head-on. With lyrics like "You're not living unless you're willing to do some dying along the way," it reminds us that growth and happiness often spawn from facing difficulties and embracing the unknown.

‘No Better Time’ inspires listeners to accept life's journey with courage and enthusiasm, unafraid of chasing their dreams because, after all, “Sweat on your skin’s better than regret on your heart”.

It claims the fourth spot because of its message to take chances and embrace uncertainty. Taking risks can be daunting, but lyrics like these fill us with courage.

Big Loud Texas / Mercury Records | 2023

To Be Free

‘To Be Free’ beautifully captures the feeling of youth and rebellion, while also mixing in deep ponderings about life and our existence.

When he sings, "smells like weed and gasoline", it's as if you can almost smell it yourself. Similarly, the lyrics, "save your time while it’s cheap", invites you to make the most of your time while you still can. Gossett masterfully conveys the idea of breaking free from society's rules and embracing freedom in the face of uncertainty.

The raw, emotional power in Gossett's writing helps listeners connect with him in a profound way. Through his emotive lyrics and sincere vocal delivery, ‘To Be Free’ helps us feel less alone in our shared inner call for freedom and understood at the deepest level.

Big Loud Texas / Mercury Records | 2023

Flip A Coin

‘Flip A Coin’ reflects on life's uncertainties and the search for inner peace, while simultaneously encouraging listeners to leave their worries behind and embrace the emotional ups and downs of being human. From the simple act of flipping a coin to make a decision, to thinking about life's ups and downs, Gossett stunningly captures the human experience.

Lyrics such as, “sometimes we're livin' just to die”, prompt us to live in the present and relieve ourselves of so much worry. It's a powerful reminder to find comfort in your journey along the way.

This is a strong contender for the top spot simply because of its sheer poetic brilliance. The way Gossett captures deep existential questions so clearly and meaningfully shows his true artistry. With his blessing, we can feel more affirmed to take risks, make the leap and know that, at least for today, we’ll be just fine.

‘Flip A Coin’ finds Gossett poised to be one of the greatest rising songwriters country music has seen in years.

Big Loud Texas / Mercury Records | 2024

Bitter Winds

Here we find Gossett lamenting about how time keeps moving forward and doesn’t wait for you to catch up. Begging to the heavens with descriptions and heartfelt words like, Can this all just please slow down / Another year is burning out / The sun don't wait for someone like me”, it underpins how time slips away too fast.

From leaves changing in the fall, reminding us that winter is coming, to moments evaporating all too quickly, ‘Bitter Winds’ reminds us to enjoy life’s little moments and appreciate what we have right now.

Without a doubt, ‘Bitter Winds’ is Gossett’s best offering thus far. His raw, passionate pleas for time to slow down strike deep, demonstrating his ability to capture the frightening yet all too relatable sensation that time is slipping through our fingers no matter how desperately we try to hold on to it.


Subscribe and listen to Holler's Dylan Gossett Songs Ranked Playlist below:


For more on Dylan Gossett, see below:

Written by Nate Boggs
Content Sponsor
Artist - Tyler Childers 3

ESSENTIALSTyler Childers Albums - Ranked

Artist - George Strait 2

ESSENTIALSThe Best Country Song Lyrics

Holler Country Music

GUIDEA Guide To: What Is Americana?

Bob Dylan

ESSENTIALSThe Best Bob Dylan Country Songs