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Top 20 Greatest Duet Songs of All Time

Top 20 Greatest Duet Songs of All Time
VOICE OVER: Rebecca Brayton WRITTEN BY: Mimi Kenny
These are the duets that put U and I together. For this list, we'll be looking at the best collaborations between two prominent vocalists. Our countdown includes "Under Pressure," "Unforgettable," "The Boy is Mine," and more!

#20: “The Boy is Mine” (1998)
Brandy & Monica


Many duets are about celebrating and supporting one another. However, “The Boy is Mine” is about fighting to get your way. Both Brandy and Monica were rising R&B stars, and it was assumed they were rivals. So, they smartly made a song playing off that assumption. The two singers exchange verses back and forth about why they each claim a man as being theirs. After this strong r&b duet achieved massive success, the rumors of a feud only spread more. Brandy and Monica’s representatives even had to publicly state that everything was cool. More than 20 years later, we don’t know which singer won this song. But we do know that this it’s a classic.

#19: “Don’t Let the Sun Go Down on Me” (1991)
George Michael & Elton John


“Don’t Let the Sun Go Down on Me” had already been a massive hit for Elton John when he first released it in 1974. But it took on a new significance 17 years later when he recorded a live version with George Michael. The two had previously performed the song together at Live Aid in 1985. Six years later, they hadn’t lost their way. When Michael starts off the song, the crowd is already roaring in approval. But the energy goes off the charts when he brings out JOhn. Hearing these two legends harmonizing is one of those moments that can’t be described, only felt. Although we wish we could’ve experienced it in person, we’re happy we got to experience it all.

#18: “Hate that I Love You” (2007)
Rihanna feat. Ne-Yo


Have you ever loved someone so much it’s practically infuriating? Rihanna and Ne-Yo know just how you feel. On this folk-influenced duet from Rihanna’s third album “Good Girl Gone Bad,” the R&B superstars sing about their mutual devotion and frustration towards each other. Why are they so fed up? As it turns out, they love each other so much that it hurts. Their voices sound perfect together over musical elements like the bright guitar strums and handclaps. This song is incredibly relatable to anyone who’s ever been crazy in love. Honestly, we don’t hate how much we love this song.

#17: “You Don't Bring Me Flowers” (1978)
Barbra Streisand & Neil Diamond


Few number-one hits have stranger journeys to the top than this one. "You Don't Bring Me Flowers” was first meant to be Diamond's theme song for the forgotten sitcom "All That Glitters." The longer version he recorded ended up being covered by Streisand. Eventually, radio stations combined the two recordings together to create unofficial duets. This roundabout way to show the vocal chemistry between the singers led to an official song being recorded. “You Don’t Bring Me Flowers” became one of the best heartbreak duets ever made, with both Diamond and Streisand expressing their pain with utter passion. Although it’s hard to end a relationship, songs like this let you know you’re not alone.

#16: “Stop Draggin' My Heart Around” (1981)
Stevie Nicks & Tom Petty and the Heartbreakers


Stevie Nicks had plenty of experience singing about heartbreak. So, it’s only fitting that she made a song with Tom Petty & the Heartbreakers. Nicks originally wasn’t involved with “Stop Draggin’ My Heart Around. Fortunately, producer Jimmy Iovine brought her on board so she could shine in this great blues-rock ballad. Nicks’ powerhouse vocals kick things off as she sings to a lover played by Petty that she’s trying to distance herself from. Eventually, their voices come together in the epic chorus and bridge. This song was Nick’s biggest hit as a solo artist as well as the biggest for the Heartbreakers. Never underestimate the power of relationship woes.

#15: “Time to Say Goodbye” (1996)
Sarah Brightman & Andrea Bocelli


Andrea Bocelli’s “Con te partirò” was already a worldwide hit. But when a new version was recorded with English vocalist Sarah Brightman, it became even more of a sensation. Despite its English title, “Time to Say Goodbye” is mostly sung in Italian. The separate and combined beauty of Bocelli’s tenor and Brightman’s soprano assures that no emotions are lost in translation. Although it sounds more appropriate for a concert hall than a sports arena, this duet was conceived as the theme song for retiring German boxer Henry Maske. It was also performed at his final match. Talk about a knockout.

#14: “I Knew You Were Waiting (For Me)” (1987)
Aretha Franklin & George Michael


When a duet is about how intensely two people care about each other, the people singing it better be able to sell it. While Aretha Franklin and George Michael might not seem like the most obvious pairing, the Queen of Soul was a fan of Wham! Her appreciation for them may be why she and Michael achieved great chemistry. “I Knew You Were Waiting (For Me)” has a great dance groove backing Franklin and Michael’s verses. When their voices come together for the chorus, it reaches new heights. While we didn’t know we were waiting for this song, we’re sure glad to have it.

#13: “Don’t Give Up” (1986)
Peter Gabriel & Kate Bush


Although pulling off a song that’s both downtrodden and hopeful is difficult, Peter Gabriel and Kate Bush pull it off. On “Don’t Give Up,” the former Genesis frontman sings with anguish as a man who feels overwhelmed by struggles. But Bush’s angelic vocals offer assurance that bad times don’t last. Recorded during a time of economic difficulty in England, "Don't Give Up's" message is applicable to any era and any place. While things might be hard sometimes, this song reminds us to keep going, even if we have to take things one moment at a time.

#12: “I Got You Babe” (1965)
Sonny & Cher


“I Got You Babe” is one of those love songs that just feels timeless. This song sees the then-married couple Sonny & Cher about their love for each other amidst all the world’s uncertainty. It’s a simple concept that’s done extraordinarily well thanks to the harmony achieved between Sonny & Cher. Throughout the duet, they really sell the story of a couple that can persevere through anything. The song’s production also deserves praise for bringing in instruments not commonly found in chart-topping pop music, such as bassoon and oboe. Ultimately, Sonny & Cher didn’t stay together. But this song still makes us believe in the power of love.

#11: “Somethin’ Stupid” (1967)
Frank Sinatra and Nancy Sinatra


More than a few people have found it a little disconcerting that this song was recorded by a father and his daughter. Despite “Somethin’ Stupid” raising a few eyebrows, it actually became “somethin’ successful.” The legendary crooner and his daughter covered a song first recorded by C. Carson Parks and his wife Gaile. This new version became a number one hit. “Somethin’ Stupid” is a lovely song, full of enchanting elements like strings and trumpets. We think it would still work if Frank Sinatra had picked a more traditional collaborator for this kind of song.

#10: “Ebony and Ivory” (1982)
Paul McCartney feat. Stevie Wonder


It shouldn’t take long for you to realize that “Ebony and Ivory” is about more than the keys on a piano. Paul McCartney enlisted fellow legendary musician Stevie Wonder for this song about racial equality. Whie some viewed the song's messaging and use of a piano as a metaphor to be cheesy, it still made a big splash. It reached number one in the U.S. and U.K. On the other hand, it also stoked some controversy and was banned in South Africa during apartheid. While “Ebony and Ivory’s’” message might have garnered a mixed response, we can hopefully agree on one thing: Paul McCartney and Stevie Wonder’s voices sound great together.

#9: “(I’ve Had) The Time of My Life” (1987)
Bill Medley & Jennifer Warnes


“Dirty Dancing” left many imprints on popular culture. But the one aspect everyone remembers today is its main theme song. Originally, “(I’ve Had) The Time of My Life),” was meant for Joe Esposito and Donna Summer. But it ended up being recorded by Righteous Brother Bill Medley and singer Jennifer Warnes. The track beautifully balances Medley’s deeper tones, Warnes’s softer voice, and the song’s irresistible pulse and romantic lyrics. A beautiful combination of elements ensured that it was an Oscar-winning smash hit. Listeners had the time of their lives with this song! Decades later... [SB]

#8: “Don’t Go Breaking My Heart” (1976)
Elton John & Kiki Dee


A song about pleading to a lover not to let you down might seem like it’ll be emotionally devastating. But in the hands of Elton John and Kiki Dee, it becomes rather joyous. Inspired by classic Motown duets, “Don’t Go Breaking My Heart” is a wonderfully energetic song. John and Dee manage to put so much into their individual singing and still find harmony. Their chemistry is especially apparent in the music video, which finds the two embracing as they share a microphone. The hit marked a significant moment for John, as it was the first time he topped the charts in the U.K. He also recorded another successful version in the 90s with none other than RuPaul.

#7: “Unforgettable” (1991)
Natalie Cole with Nat King Cole


The father-daughter duet “Unforgettable” was released more than 25 years after Nat King Cole had passed away. He had first recorded and released the song in 1951. But his daughter Natalie made a new version for her “Unforgettable... with Love,” an album of songs her father had previously recorded. “Unforgettable” brought the pair together for a “virtual duet.” And while they might not have been physically singing together, the Coles sound flawless and timeless here. This song was already unforgettable, but this version made us love it even more. We’re sure Nat King Cole would be touched to know his daughter was celebrating his legacy like this.

#6: “Islands in the Stream” (1983)
Kenny Rogers & Dolly Parton


A duet between Kenny Rogers and Dolly Parton is a match made in country heaven. But “Islands in the Stream” could’ve gone in a different direction. Written by the Bee Gees, this song was originally written for Marvin Gaye. After it was later offered to Rogers, he became frustrated by the recording. His suggestion to bring in Parton was a stroke of genius. "Islands in the Stream" became a number-one hit. Even if you’re not a country fan, you’ll enjoy how Rogers and Parton harmonize. It also sparked a fruitful collaborative career between the two. They later released a Christmas album the following year and another hit, “Real Love,” the next. Kenny Rogers might have been “The Gambler,” but this bet paid off.

#5: “When You Believe” (1998)
Mariah Carey & Whitney Houston


A duet between Mariah Carey and Whitney Houston was bound to be a showstopping event. The two divas definitely delivered with “When You Believe.” Written for “The Prince of Egypt,” the song’s lyrics follow the animated film’s themes of faith and miracles. Carey and Houston both deliver commanding performances that remind us why they’re so revered. The duet also received the Oscar for Best Original Song. Sadly, Houston is no longer with us. But this song makes us feel like she’s still here and offering us hope. The fact that this song exists and it’s this good is a true miracle.

#4: “Endless Love” (1981)
Diana Ross & Lionel Richie


If there are two singers who know their way around a ballad, it’s Diana Ross and Lionel Richie. The R&B stars came together for “Endless Love.” This was touted as the theme song for a film of the same title. While the movie wasn’t very well received, the song quickly reached legendary heights. It hit number one on multiple charts and reached Platinum sales status. There are no gimmicks to this classic either. Throughout the track, we just appreciate having two wonderful singers find harmony in both their voices and in their words and never lose their passion. Our love for this song is endless as well.

#3: “Ain’t No Mountain High Enough” (1967)
Marvin Gaye & Tammi Terrell


Marvin Gaye and Tammi Terrell recorded numerous duets together for Motown Records. But the biggest and best was their first. “Ain’t No Mountain High Enough” is an ode to love so intense, it can’t possibly be measured. It’s impossible to not get swept up by Gaye and Terrell’s energy. The backing percussion and other instrumentation give the song even more passion. Although Gaye and Terrell didn't record their vocals together, their chemistry is still off the charts. It peaked at number 19 on the Hot 100 before another version recorded by Diana Ross hit number one. When you want to be uplifted by love, it’s hard to think of a better song.

#2: “Under Pressure” (1981)
Queen & David Bowie


Nothing says “glam” quite like a collaboration between Freddie Mercury and David Bowie. Immediately identifiable by its iconic bassline, which was later sampled by Vanilla Ice for “Ice Ice Baby,” “Under Pressure,” is a chart-topper that goes into some deep topics. It namely explores the day-to-day dread of navigating the world. But it’s difficult to feel despair when you have the combined power of those two vocalists. Even in its quieter moments, “Under Pressure” is brimming with emotion. Both Queen and Bowie had legendary careers, but this song showed how great they could be with their powers combined.

#1: “Say Say Say” (1983)
Paul McCartney & Michael Jackson


Recording a duet with Paul McCartney is a big ask for any artist, even one as accomplished as Michael Jackson. But the Beatle and the King of Pop achieved musical greatness with “Say Say Say,” a duet for McCartney’s solo album, “Pipes of Peace.” The two icons certainly show off their pipes with this chart-topper. It’s a funky banger about trouble in love. But even if the lyrics are moody, the song is bound to put a smile on your face. It’s the kind of song we wish we could do at karaoke, but we’re scared we don’t have the vocal chops for it. McCartney and Jackson also found success with “The Girl is Mine.” But we’ll always go, go, go for “Say Say Say.”

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