Kenny Rogers' 10 Best Songs: Critic's Picks

Kenny Rogers performs at the Rosemont Horizon on May 17, 1980.
Paul Natkin/Getty Images

Kenny Rogers performs at the Rosemont Horizon on May 17, 1980.

Kenny Rogers has enjoyed one of the most iconic careers in the history of not just music, but the entertainment business. He has enjoyed success as a singer, an actor, an author, and of course -- who can forget Kenny Rogers’ Roasters -- his brand of chicken restaurants in the 1990s? We bet Jerry Seinfeld won’t anytime soon?

Coming up with a list of ten of the best Kenny Rogers songs is almost a downright impossible task. You could do separate essays on his 60s and 70s hits with The First Edition, and his duets -- with Dolly Parton, Dottie West, Kim Carnes, and Sheena Easton (among others) would warrant a list all to themselves. So, in picking ten of Rogers’ best, we decided to keep things limited to his country successes that began in the mid 1970s, and strictly to his solo works. As Rogers prepares to hang up his touring shoes, here are ten moments that rank high on the hit parade for the Country Music Hall of Fame member!

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10. Kenny Rogers - "She Believes In Me"

Released as the follow-up to “The Gambler” in the spring of 1979, Rogers took Steve Gibb’s lyrics that paid tribute to the woman behind a man still trying to make it in the music business. Larry Butler’s production offered a dramatic element to the song, which topped the Country and Adult Contemporary charts -- and hit No. 5 on the Hot 100.

9. Kenny Rogers - “I Prefer The Moonlight”

Rogers’ 1983-1988 era on RCA resulted in some fine recordings -- including the blockbuster “Islands In The Stream” duet with Parton. However, some of his later work from the period tends to get overlooked -- in spite of continued success on the singles chart. The singer hit No. 2 in the holiday period of 1987-88 with this Mark Wright / Gary Chapman cut that is one of his more traditional country moments, sprinkled with some nice harmonies from Kim Carnes and some tasty fiddle work from Mark O’Connor.

8. Kenny Rogers - “The Greatest”

Rogers turned to Don Schlitz in 1999 for this unlikely hit that compared life to playing baseball. Always a magician with a lyric, Schlitz’s turning the boy’s bad play into an exercise in philosophy turned out to be stroke of genius, providing the singer with his first entry into the Top 30 in eight years. Of course, it’s not the only Schlitz composition to wind up on this list!

7. Kenny Rogers - “Morning Desire” 

Dave Loggins was one of the hottest songwriters in Nashville during the 1980s, and the singer had Loggins as a guest at his house, hoping he could come up with something special. As it turned out, the man who made “Please Come To Boston” a classic in the 1970s did just that, coming up with an arrangement that was putty in Rogers’ capable hands. The song was one of two singles that Sir George Martin produced on the singer, with the other one being “Tomb Of The Unknown Love.” A gorgeous touch on this record was the unforgettable guitar solo of jazz guitarist Stanley Jordan.

6. Kenny Rogers - “Lady”

One of two classics on this list to have a tie to Lionel Richie, one couldn't go anywhere in the fall of 1980, and not hear this romantic song of love. Proving to be the perfect marriage of country and pop, Richie pitched the song idea to Rogers before he had even written the song. After Kenny approved the song, he had to finish the song quickly. The recording marked one of the first times that a song was placed on a Greatest Hits package without being a single prior. Of course, the song became one of his biggest -- propelling the CD to become a Diamond-selling album.

5. Kenny Rogers - “Twenty Years Ago”

Rogers added the right touch of longing and nostalgia on this 1986 single, which stopped just shy of the number one position. The song’s lyrics paid homage to the memories that the lead character in the song had of the town growing up -- when things were much more simple and serene than they were in the pre-Vietnam era. Country was in the midst of a swing back to a more traditional sound, which might help to explain the reason why this song doesn't get the credit it deserves, but it’s a Kenny Rogers song that stands as one of his best.

4. Kenny Rogers - “I Don’t Need You”

After the success Rogers enjoyed with Richie on “Lady,” the singer allowed him to steer his musical fortunes with the album Share Your Love, and the resulting factor was one of his finest efforts. At the center of the disc was this ballad that was perhaps Rogers at his most soulful. The fans certainly thought so, making this one a country and AC chart-topper.

3. Kenny Rogers - ‘Lucille”

Hal Bynum and Hal Bynum provided Rogers with what turned out to be the lightning rod for his move into country music with this haunting mid-tempo number about a man who is just about to fall to the advances of his new female love interest, but can’t seem to get the words that her husband said to her earlier in the evening out of his mind. If nothing else, one of the biggest country hits to ever be set in Toledo, Ohio!

2. Kenny Rogers - “Sweet Music Man”

Sandwiched between chart-toppers “Daytime Friends” and “Love Or Something Like It,” the No. 9 peak of this one was among the lowest of Rogers’ hits on United Artists. But, it could very well be his overall greatest performance. Written from the perspective of a woman who has had enough of watching as her lover gives of himself to everyone in his career -- but not her, you can tell that Rogers felt every word of this one first-hand. But, even in her leaving, the woman had to admit that “Nobody Sings A Love Song Quite Like You Do.”

1. Kenny Rogers - “The Gambler”

Even if Don Schlitz’s story of a late-night card game on a train seemingly “bound for nowhere” had never been a single, it still might be the greatest Kenny Rogers song of all-time. Each line of this song effortlessly flowed into the next one, setting the stage for a chorus that fans all over the world will be singing for years from now till eternity. Plus, the song’s success established a persona for Rogers that will live forever, and gives most interviewers their first question - ‘How does ‘The Gambler’ fit into your personal philosophy?’ The bottom line is this -- the song will continue to live a lot longer than any of us!