18 Songs About Cowboys

Exploring songs about cowboys takes us on a journey through tunes that encapsulate the essence of the wild west, freedom, and the cowboy lifestyle. From the longing of the open range to the heartfelt stories told through lyrics, these tracks by artists like Toby Keith, George Strait, and The Chicks celebrate the iconic cowboy imagery and spirit.

1. “Should’ve Been A Cowboy” by Toby Keith

“Should’ve Been A Cowboy” by Toby Keith has become an anthem for all those who romanticize the cowboy lifestyle, capturing the hearts of listeners with its catchy melody and vivid storytelling. The song taps into widespread appeal by reflecting on modern desires to embrace simpler, more adventurous times, echoing the common wish to break free from the constraints of contemporary life and embody the freedom and valor of the cowboy dreams.

2. “The Cowboy Rides Away” by George Strait

“The Cowboy Rides Away” by George Strait delves into the poignant themes of endings and transitions, capturing the bittersweet nature of saying farewell. Through its emotive lyrics and George Strait’s iconic voice, the song becomes a powerful symbol of the end of an era, not just for cowboys but for country music legends and their fans, marking a reflective moment of change.

3. “Cowboy Take Me Away” by The Chicks (formerly Dixie Chicks)

“Cowboy Take Me Away” by The Chicks captivates listeners with its deep yearning for escape and adventure, narrated through a cowgirl’s perspective. This song skillfully blends modern country sounds with traditional themes, illustrating a desire to break away from the mundane, seeking freedom and solace in the open arms of the wild, unchained landscapes and cowboy romance.

4. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” by Willie Nelson & Waylon Jennings

“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” by Willie Nelson & Waylon Jennings offers a blend of humorous and poignant advice, warning of the hard life that accompanies the cowboy lifestyle. This song has left a substantial impact on the country music genre, cleverly using wit and wisdom to convey the challenges of being a cowboy while also celebrating the allure and freedom it represents.

5. “I Wanna Be a Cowboy” by Boys Don’t Cry

“I Wanna Be a Cowboy” by Boys Don’t Cry stands out as an 80s hit that adopts a lighthearted, almost parody-like approach to the cowboy image, diverging sharply from the earnest and often romanticized portrayals in traditional songs about cowboys. This track cheekily taps into pop culture, showcasing a playful take on the cowboy lifestyle that resonated with audiences, offering a contrast to the more serious themes usually found in this genre.

6. “Cowboys Like Us” by George Strait

“Cowboys Like Us” by George Strait celebrates the camaraderie among cowboys and the unparalleled sense of freedom experienced on the open road, capturing the essence of brotherhood and liberty that define cowboy life. George Strait, through this song, continues to leave an indelible mark on the country music genre, skillfully portraying the depth and allure of the cowboy lifestyle with his iconic voice and heartfelt lyrics.

7. “Rhinestone Cowboy” by Glen Campbell

“Rhinestone Cowboy” by Glen Campbell delves into the aspirations and dreams of fame and fortune, portraying a vivid reflection of the personal journeys artists and cowboys alike embark upon. This classic tune resonates with listeners by highlighting the pursuit of success in the face of challenges, encapsulating Glen Campbell’s own experiences and the universal quest for recognition and achievement in the glittering yet tough arenas of the music and rodeo worlds.

8. “Save A Horse (Ride a Cowboy)” by Big & Rich

“Save A Horse (Ride a Cowboy)” by Big & Rich presents a playful take on cowboy imagery, marking a distinctive moment in the evolution of 2000s country music. This track stands out for its upbeat rhythm and humorous lyrics, offering a fresh perspective on modern cowboys and injecting a dose of fun into the genre, reflecting Big & Rich’s unique ability to blend traditional themes with contemporary sounds and attitudes.

9. “Like A Cowboy” by Randy Houser

“Like A Cowboy” by Randy Houser explores the emotional depth behind a cowboy’s love story, showcasing Randy Houser’s powerful vocals and exceptional storytelling ability. This song draws listeners into a heartfelt narrative, highlighting the complexities and sacrifices inherent in love and life on the road, embodying the spirit and resilience of cowboy romance with evocative imagery and deeply moving melodies.

10. “Cowboy Casanova” by Carrie Underwood

“Cowboy Casanova” by Carrie Underwood delves into the portrayal of a cowboy as a heartbreaker, offering a cautionary tale set against a backdrop of catchy country pop melodies. This song blends traditional narratives of cowboys with modern sounds and themes, showcasing Carrie Underwood’s dynamic vocal range and storytelling prowess, warning listeners about falling too hard for a cowboy known more for his charms than his commitment.

11. “A Cowboy’s Prayer” by Sons of the Pioneers

“A Cowboy’s Prayer” by Sons of the Pioneers dives deep into the spiritual and reflective nature of the cowboy’s life, capturing a sense of reverence and contemplation. This song acknowledges the historical and cultural significance of cowboys, offering listeners a window into the introspective and solitary moments that punctuate the rugged lifestyle, underscored by the harmonious vocals of the Sons of the Pioneers.

12. “Cowboys and Angels” by Dustin Lynch

“Cowboys and Angels” by Dustin Lynch explores the captivating contrasts between the stereotypical outlaw image of cowboys and the angelic figures that reveal their softer, more vulnerable sides. This hit song weaves a narrative that combines ruggedness with tenderness, showcasing Dustin Lynch’s ability to navigate the complexities of these relationships through his emotive lyrics and soul-stirring melodies, highlighting the dichotomy between strength and gentleness in the cowboy persona.

13. “The Cowboy In Me” by Tim McGraw

“The Cowboy In Me” by Tim McGraw offers an introspective look at the cowboy spirit that resonates within, speaking to the universal appeal of self-discovery and independence. Through his compelling storytelling and emotive performance, Tim McGraw captures the essence of wrestling with one’s own desires for freedom and the constraints of life’s responsibilities, making this song a powerful anthem of self-reflection and the longing for a simpler, more unbridled existence.

14. “Cowboys Are Frequently, Secretly Fond of Each Other” by Willie Nelson

“Cowboys Are Frequently, Secretly Fond of Each Other” by Willie Nelson stands out as a groundbreaking exploration of cowboy companionship, addressing themes of love and secrecy within the conservative backdrop of country music. This unconventional song by Willie Nelson breaks barriers, boldly discussing the complexities of affection and identity among cowboys, proving to be a significant moment in the genre for its open discussion of topics often left unexplored.

15. “Amarillo By Morning” by George Strait

“Amarillo By Morning” by George Strait captures the essence of rodeo life and the relentless pursuit of dreams, making it one of his most beloved tracks. Through the song’s poignant lyrics and George Strait’s iconic delivery, listeners are transported into the world of cowboys who face the hardships and uncertainties of the road, all while chasing the flickering light of success in the competitive arena, embodying the true spirit of endurance and hope.

16. “This Cowboy’s Hat” by Chris LeDoux

“This Cowboy’s Hat” by Chris LeDoux delves into the symbolic importance of the cowboy’s hat, representing much more than a piece of attire but rather a deep connection to identity, legacy, and personal values. Through this song, Chris LeDoux weaves a narrative that brings to life the significance of the hat as a badge of honor and resilience, echoing the sentiments and stories of cowboys across generations.

17. “Cowboy Man” by Lyle Lovett

“Cowboy Man” by Lyle Lovett presents a unique take on the cowboy persona, blending undeniable charm with traditional country elements. Lyle Lovett’s distinctive voice and clever lyrics paint a picture of a cowboy who is not only rugged and adventurous but also charismatic and appealing, offering a fresh and engaging perspective on what it means to embody the spirit of the West.

18. “My Heroes Have Always Been Cowboys” by Willie Nelson

“My Heroes Have Always Been Cowboys” by Willie Nelson delves into the idolization of cowboys and the nostalgia for a way of life that seems to be disappearing. Willie Nelson eloquently expresses a deep admiration for the cowboy ethos, highlighting the qualities of heroism, independence, and a connection to nature that have made cowboys enduring symbols of American culture and personal aspiration.