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In the history of country music, few artists are on the same level as Kenny Rogers. While he may have dabbled in other genres, Rogers was a country boy at heart, and that’s what he did best. Therefore, it only seems fitting to remember the 10 best country music songs that Rogers sang during his memorable career.


10. Evening Star

Rogers’ album Eyes That See in the Dark was a pop smash, which most people wouldn’t have expected with Barry Gibbs as the producer. The most country hit on the album by a mile was “Evening Star.” Featuring backup vocals from the Gatlin Brothers and a distinctly Western vibe, it’s a beautiful and straightforward song, which is exactly what we’ve come to expect and love from Rogers.


9. Just Dropped In

Rogers’ first major hit with the First Edition was unconventional in line with what would become his signature musical style. It was a psychedelic rock tribute to LSD that became an anthem for hippies and Big Lebowski fans. It’s a noisy, experimental, and strange song that doesn’t sound as popular as it was. However, the chart success of “Just Dropped In” speaks for itself. This song is a massive hit and a pop culture touchstone, symbolizing a whole generation’s trippy tendencies.


8. While the Feeling’s Good

Commercially, this song was a flop. It came out before Rogers found mainstream success. However, aesthetically, it showcased how well Rogers could blend into the Nashville Sound. It’s an emotional song with a contemporary, smooth groove. It offers a glimpse into the seductive side of country music, an aspect Rogers didn’t explore that much throughout his career. That makes “While the Feeling’s Good” a taste of the path not taken, which is why it’s one of his best in retrospect.


7. Share Your Love with Me

Singing a song after Aretha Franklin not only performed it but also won a Grammy for it takes courage. However, Rogers achieved arguably the biggest hit of his career with the Lionel Richie composition “Lady.” Rogers’ version is a perfect mix of country and R&B that somehow had pop appeal as well. This song continues to serve as compelling evidence that with the right artist, genre-blending songs can be something truly special.


6. Love Will Turn You Around

Released at the height of his success, “Love Will Turn You Around” was a masterclass in understatement. The song features a simple acoustic riff while Rogers tells a familiar story about the power of love. His conversational singing style combined with the melody is captivating yet somehow effortless. The song’s folksy vibe offered a nostalgic nod to Rogers’ earlier work and became his fourth song to reach the top of both the country and adult contemporary charts.


5. Sweet Music Man

Nothing about “Sweet Music Man” suggests “major hit.” Rogers has released the track multiple times. It’s also been covered by several prominent artists, including legends like Dolly Parton and Reba McEntire. Yet, it’s hard to find a sweeter melody or refrain (“Nobody sings a love song quite like you do”), which is why generations of music lovers have been enchanted by it.


4. Lady

If Rogers wasn’t fully aware of the quiet storm movement in R&B, Lionel Richie, who wrote and produced the biggest single of Rogers’ career, certainly was. Richie’s influence is evident in “Lady” thanks to its super-slow tempo and conversational balladry that’s reminiscent of the sultry R&B hits of the time. The song was a massive success, staying atop the Hot 100 for six consecutive weeks and charting on the AC, country, and soul charts. This song, perhaps more than any other, solidified Rogers’ status as a bona fide pop star in addition to being a legendary country singer.


3. Lucille

The legend of “Lucille” is that Rogers, newly solo after his time with The First Edition, was performing as a Vegas lounge act and offering music lessons when he discovered the song in a pile of discarded tracks at a Nashville publishing office. The song is perfectly crafted and undeniably catchy. Despite never getting to no. 1 on the charts, it was his breakout hit, establishing Rogers as a folksy, acoustic star. All these years later, who can resist singing along to “Lucille” when they hear it?


2. Islands in the Stream

This hit song might be the happiest ever. It was a post-disco masterpiece tailored to Rogers’ and Dolly Parton’s unique blend of pop and country. Originally written by the Gibb brothers for Marvin Gaye, it’s hard to picture anyone else delivering its quirky charm so effectively. Kenny and Dolly made a captivating duo and this song remains the perfect example of that.


1. The Gambler

There is no doubt that “The Gambler” is Rogers’ best and most famous song. He won a Grammy for Best Male Country Performance for it, although that award doesn’t do the song justice. It’s a timeless classic that’s still played more than four decades later. True to its name, it’s still one of the best songs about the art of gambling. Perhaps that’s why “The Gambler” has become such a timeless classic.

Nowadays, gambling has become more mainstream than ever in all corners of the world. For example, even north of the border, thousands of miles from Rogers’ hometown of Houston, there are many popular Canadian betting sites that offer a safe and trustworthy platform for gambling. In a weird way, this makes “The Gambler” more relatable than ever.

Alexandre G.
He’s just a guy who got tired of bothering his friends with talk about music, so he decided to create a blog to share what he loves most.
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