Considering their respective legacies, neither Dolly Parton nor Kenny Rogers need much of an introduction! Rather than give you a cold "Here are some facts about both people" opening, how about this? I'll let Parton herself explain how much Rogers meant to her and the impact he had on her life!
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Speaking to PEOPLE, here's how Parton summed up an eternal bond that spanned decades. "I've lost so many wonderful people in my life in the last few years. But Kenny — he was very, very dear and special and I never get tired of hearing us sing, all the years that we were on stage together."
The subject here, of course, is Dolly Parton and Kenny Rogers songs. In fact, it's more specific than that! Today, dear reader, we're going to talk about Parton and Rogers' duets, the best of which I'll assemble in this upcoming list!
Dolly Parton And Kenny Rogers - The Beginning: "Islands in the Stream" (1983)
The pair's first-ever duet skyrocketed to the #1 spot on Billboard's Hot 100 chart! Not only did it dominate that chart, but it also basically swept the Country and Adult Contemporary charts, too! Additionally, it went triple Platinum -- selling over three million certified units.
It's no big secret, this is Rogers and Parton's best duet, hands-down. I'm sorry to ruin the mystique of the typical "listing format," but I'm not going to lie to you! It's both musicians at their absolute best! Plus, you can see the signs of their lifelong connection in their performance and hear it in their voices. It's perfect. There's no doubt that this is Kenny Rogers and Dolly Parton's most famous song together!
A Year Later: 'Once Upon a Christmas' (1984)
So, this is cheating a bit, but there's a method to my madness! Once Upon a Christmas was Rogers and Parton's first (and only) collaborative album! It won the Canadian Country Music Association award for "Top Selling Album" in 1985. It didn't do too shabby on Billboard's charts, either. It peaked at #12 on the Top Country Albums chart, which is still an achievement!
In an issue of Cashbox, Parton would say the following about the album. "This is the first Christmas special or album that I've ever done, so when Kenny called me with the idea, I jumped at it. ... I think the blend of our voices creates a real electricity that comes across on record. He also has a real Santa Claus spirit."
Obviously, it'd be torture for everyone if I painstakingly "ranked" the entire album. However, we can certainly go over some of the highlights!
"The Greatest Gift of All" (1984)
Critic Mode Activate! Personally, this is my favorite song on the entire album. It somehow does a delicate tightrope balance between "Christmassy" and "Romantic." It's uplifting, too! You might get a few weird looks for playing this outside of the "festive season." But it's not entirely inappropriate to blast this one whenever you feel the need to play it!
"Christmas Without You" (1984)
Now, "Christmas Without You" retains the romantic aspect, but it's decidedly more "Christmas" in its pace! It's more upbeat and fun, focused on the traditional aspects of the holiday. Snow, mistletoe, sleigh bells -- all that good stuff!
"I Believe in Santa Claus" (1984)
This one is more of a sprightly hoedown! Truthfully, this deserves to be shouted out just for blending Country and Christmas so effortlessly! If you felt so inclined, you could even dance to it. Me, I'm no dancer. I'm a "tasteful head nod" kind of music connoisseur.
"Once Upon a Christmas" (1984)
"Once Upon a Christmas" isn't for folks who would rather ignore Christmas' religious undertones. However, it's an exceptionally soulful song. Parton and Rogers unify to belt out a song that touches your emotional core. Nothing wrong with listening to a song just to feel it -- and this one epitomizes that transformative listening experience!
"Real Love" (1985)
They were really cranking the hits out one after another! "Real Love" topped Billboard's US Hot Country Songs charts! It didn't fare quite as well as "Islands," but it still ended up being impactful! Parton and Rogers have always maintained that their relationship was "friendly."
But, come on. Listen to this song, watch the two, and tell me there's no smoky romance brewing beneath the surface! "Real Love" is an all-timer by default, but it's not exactly the Rogers/Parton song I'd be champing at the bit to play.
"Love Is Strange" (1989)
We've got an "underrated classic" on our hands! "Love Is Strange" doesn't get nearly the respect it deserves! It's an amazing song; it perfectly captures the feeling of falling in love with someone when you're young and in the honeymoon phase of a new relationship.
There's that "fun nostalgia" edge to it that hopefully doesn't make you think of love lost. The last thing I want to do is make people sad. It's okay, though. We're moving on!
The Mid-Point: "Undercover" (2003)
"Undercover" is an interesting entry in the duo's musical journey. It's a good song, don't get me wrong! But it's certainly darker in tone than the rest of their duets so far. If "Love Is Strange" is fresh love right from the oven, "Undercover" is when the relationship has some mileage.
Those darker aspects are on full display with allusions to confronting one's "demons." Despite the melancholic undertones, there's still a sense of warmth and comfort to the song.
The Gap: "Tell Me That You Love Me" (2009)
"Tell Me That You Love Me" didn't see the light of day until 2023. The song itself was thought to be lost forever. But, it resurfaced on Rogers' final album released after his passing, Life Is Like a Song. There's a lost optimism present in this track. The love has faded, and insecurities have risen to the surface.
Though it was recorded in 2009, it feels like a song perfect for a "final" album celebrating one of the greatest musicians of all time. It also fits with the longing of wishing someone was there when they simply can't be anymore.
Dolly Parton And Kenny Rogers - The End: "You Can't Make Old Friends" (2013)
We're unfortunately ending things on a dour note. "You Can't Make Old Friends" is as beautiful as it is heartwrenching. If it weren't for the longstanding legacy of "Islands in the Stream," this would easily take the number one spot as their best duet. Rogers passed away due to bladder cancer in 2020.
It's unclear what Rogers' condition was in 2013 when "You Can't Make Old Friends" released. You have to wonder if the song was specifically meant for Parton. After a friendship spanning decades, the inevitability of The End reared its head. In the song, there's a strong sense of having lost someone who meant the world to a person. Introspective and devastating in equal measure, few songs can ever live up to the emotional nuance and meaning of "You Can't Make Old Friends."
