Remember When Jimmy Buffett Sang “Hey, Good Lookin’” With A Bunch Of Country Stars?

Jimmy Buffett defied easy genre categorization, with his music resonating across diverse audiences and serving as a source of inspiration for artists from a broad spectrum of backgrounds. From the likes of Brad Paisley to Paul McCartney, Buffett’s music had universal appeal, connecting with individuals from various walks of life.

While his musical repertoire spanned a wide range, Buffett’s roots were firmly entrenched in the realm of country music. He embarked on his career in this genre many decades ago, and he maintained a strong connection to it throughout his lifetime. 

Over the years, he engaged in fruitful collaborations with notable artists, including Alan Jackson, the Zac Brown Band, and Miranda Lambert. Having said that, it was still a monumental feat to pull together some of the best of country music to collaborate for a cover of an iconic country song.

As an opener for his 2004 hit License to Chill, Buffett recruited the services of Clint Black, Kenny Chesney, Alan Jackson, Toby Keith, and George Strait to sing a cover of Hank Williams’ “Hey, Good Lookin’”. Listen to one of country’s greatest convergence of stars below:

A feel-good collaboration

Buffett enlisted a star-studded lineup to collaborate on the rendition. This timeless classic, originally penned and performed by Williams in 1951, found its way onto Buffett’s 2004 album, License to Chill. 

The track, brimming with country music luminaries, climbed to an impressive number eight on the Billboard Hot Country Singles chart upon its release.

The song, an exuberant celebration, was flawlessly executed, with each line and verse thoughtfully divided among the talented artists. A music video for the track was also produced, directed by Trey Fanjoy and Stan Kellam, adding a visual dimension to this remarkable collaboration.

Notably, this country-infused rendition of “Hey, Good Lookin'” achieved success beyond the country charts, reaching the 63rd position on the all-genre Billboard Hot 100, a testament to the enduring charm of both the song and the extraordinary ensemble that breathed new life into it.

Jimmy brought the ‘chill’ to country

A year before License to Chill hit the shelves, Jimmy Buffett’s partnership with Alan Jackson resulted in the hit song “It’s Five O’Clock Somewhere”, which told the tale of a hardworking, underappreciated blue-collar worker yearning for a tropical escape. 

This track soared to the peak of the Country Airplay chart, claiming the No. 1 spot for an impressive eight weeks. It also made its mark on the broader musical landscape by entering the top 20 of the Hot 100 chart.

Riding on that high, License to Chill entered The Billboard 200 and became the beach troubadour’s first and only No. 1 in the said chart. In 1974, Jimmy Buffett marked his first entry onto the Billboard charts with Living and Dying in 3/4 Time, recorded under the now-defunct Dunhill/ABC label.

This album reached a peak position of No. 176 on The Billboard 200. Since that early milestone, Buffett has masterfully crafted a career distinguished by its unique and enduring success, establishing himself as a touring legend in the world of music, until his death on September 1, 2023, at the age of 76.

Jimmy’s profound influence on country music

Over his illustrious five-plus decades in the music industry, Jimmy Buffett achieved notable success on Billboard’s Hot Country Songs chart. He secured two chart-topping hits, along with three tracks that made it to the top 10, in part due to his commitment to maintaining strong connections within the country music community, collaborating with a diverse array of artists.

Notably, Chesney, as early as 1998 in his hit “How Forever Feels”, paid homage to Buffett with the line, “Now I know how Jimmy Buffett Feels,” a reference that marked the beginning of his “Island Kenny” persona, complete with the iconic cowboy hat and puka shell necklace. 

Additionally, Zac Brown Band, with tracks like “Toes”, “Jump Right In”, and their 2011 No. 1 hit collaboration with Buffett, “Knee Deep”, crafted their own signature island jam band vibe, contributing to the evolution of contemporary country music’s beach-infused sound.

Reflecting on this evolution, Jimmy Buffett memorably said this in a 2021 interview with Billboard: “When contemporary country took it to the beach, obviously we were a big part of that.”