One big name on a red-hot hit is great, but sometimes two superstar voices come together in an inspired pairing that is truly special. With Valentine’s Day’s celebration of couples in mind, our experts dove into over 50 years of Hot 100 hits to single out the biggest songs by two singers to ever hit the chart. So grab a box of chocolates, dim the lights, cozy up to that special someone and turn up the speakers as we count down the hottest duets of all time.
This chart is comprised only of songs where two singers share equal vocal duties on the track. Ranking is based on actual performance on the weekly Billboard Hot 100 since the chart launched in August 1958. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least.
Text by Keith Caulfield, M. Tye Comer, Mariel Concepcion, Jessica Letkemann, Jason Lipshutz, Jillian Mapes and Chart Beat Columnist Gary Trust
How This Chart Was Created: The 40 Biggest Duets of All-Time list includes songs that feature two singers sharing equal vocal duties on the track. Ranking is based on actual performance on the weekly Billboard Hot 100 since the chart launched in August 1958. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. Prior to the Hot 100’s implementation in 1991 of enhanced radio and sales information from Nielsen BDS and Nielsen SoundScan, songs had shorter reigns at No. 1 and shorter chart lives. To ensure equitable representation of the biggest hits from the past 52 years, earlier time frames were each weighted to account for the difference between turnover rates from those decades and the turnover rates that have occurred since the advent of Nielsen Music data.
40. The Closer I Get To You
Roberta Flack with Donny Hathaway
Just months before Donny Hathaway’s untimely death, this tender tune for Hathaway and Roberta Flack was a No. 2 hit on the Hot 100 in 1978, but it wasn’t the first star turn for a song by the pair. Their 1973 duet “Where Is The Love” won them a Grammy for Best Pop Performance by a Duo Or Group. “The Closer I Get,” meanwhile, has gone on to be covered by no less than Beyonce dueting with Luther Vandross in 2003.
39. I Just Can’t Stop Loving You
Michael Jackson With Siedah Garrett
Michael Jackson is that rare artist that can score on the charts alone, in a group, duetting with another male superstar (for example with Paul McCartney on “Say Say Say” and “The Girl Is Mine”), and, as was the case with this love ballad, pairing his lilting tones with a female singer. “I Just Can’t Stop Loving You,” which found the King Of Pop trading emotional verses with Siedah Garrett, rose to the top of the Hot 100 in Sept. 1987.
38 . I’m Your Angel
R. Kelly & Celine Dion
And the award for oddest pairing goes to… R. Kelly and Celine Dion, who came together for the duet “I’m Your Angel,” written by Kelly and featured in Dion’s “These Are Special Times” album. Released in 1998, the single reached No. 1 on the Billboard 100 chart and remained there for six weeks.
37. Wild Night
John Mellencamp With Me’Shell Ndegeocello
The “Wild Night” in question seems to have been entirely platonic in this case. There’s clearly no chemistry between Mellencamp and Ndegeocello in the video, but the two sure have a jammin’ ol’ time on the track. This version of the song, originally by Van Morrison, spent two weeks at No. 3 on the Hot 100 chart the fall of 1994.
36. The Next Time I Fall
Peter Cetera with Amy Grant
Is it possible to fall in love with the same person twice? Peter Cetera and Amy Grant (oh, and songwriter Bobby Caldwell) seem to think so. On the popular song “The Next Time I Fall,” which appears on Cetera’s 1986 album “Solitude/Solitaire,” Cetera and Grant harmonize about falling in love all over again with the same lover. Sweet!
35. I Got You Babe
Sonny & Cher
Iconic ’60-’70s husband and wife duo Sonny & Cher had several hits during their career, but none came to define the pair quite like “I Got You Babe.” The track spent three weeks atop of Hot 100 in 1965. In addition to wooing couples across the globe, the hit grew to become an easy going love ballad for the hippie generation.
34. All I Have
Jennifer Lopez & LL Cool J
Based on a sample from Debra Laws’ 1981 song “Very Special,” “All I Have,” finds J. Lo and LL Cool J talking about a couple that’s on the verge of calling it quits. Still, while the tune is about splitsville, Jenny from the block and Mr. James manage to separate in style and grace (See Jennifer’s Louis Vuittons and Gucci bags?).
33. No More Tears (Enough Is Enough)
Barbra Streisand / Donna Summer
For those weathering a breakup, two of the biggest divas of all-time are here to declare that “enough is enough.” Donna Summer commiserates with Barbra Streisand over the sad state of dealing with relationships before musically saying “Screw it! Let’s dance!” to a thumping disco beat. It is a truly glorious moment to listen to the singers bust out of their slumps — and apparently all of America thought so as well, as the song stayed at No. 1 on the Hot 100 for two weeks in 1979.
32. The Girl Is Mine
Michael Jackson and Paul McCartney
Many things are unlikely about the MJ-Macca pairing: that “The Girl Is Mine” was actually the lead single off “Thriller,” that Jackson would later buy the rights to Beatles songs behind McCartney’s back, but most of all, that the two mega-stars would ever fight over a woman. But after having a ball recording McCartney’s “Say Say Say” together in 1981, Jackson and his Beatle friend gave it another go with the cheesy, soft-rock duet. “The Girl Is Mine” peaked at No. 2 on the Hot 100, and stayed there for three weeks — probably because we were all surprised to see the two superstars singing together.
31. I Knew You Were Waiting (For Me)
Aretha Franklin & George Michael
Considering what we know now, the pairing of Aretha Franklin and George Michael on the uptempo duet “I Knew You Were Waiting (For Me)” seems a little less strange. After all, every sassy diva needs her gay BFF. But regardless of the head-scratching over its duo of performers, “I Knew You Were Waiting (For Me)” spent two weeks atop the Hot 100 chart in 1987 as well as 17 weeks total.
30. Friends And Lovers
Carl Anderson & Gloria Loring
While “Friends and Lovers” sounds undoubtedly dated, the airy duet between unlikely pairing of actors/singers Carl Anderson and Gloria Loring was all the rage in ’86. After a popular performance on the soap opera “Days Of Our Lives” — on which Loring starred as lounge singer Liz Chandler — the song spent two weeks at No. 2 on the Hot 100 chart. For those hoping to move out of the dreaded “friends zone,” Anderson and Loring have some encouragement that it’s actually possible: “We don’t have to be one or the other.”
29. Up Where We Belong
Joe Cocker and Jennifer Warnes
“Up Where We Belong” may be synonymous with the 1982 film “An Officer and a Gentleman,” but the Joe Cocker and Jennifer Warnes duet is just as romantic even when one is not staring at a super-dreamy uniformed Richard Gere. The song not only stayed at No. 1 on the Hot 100 for three weeks in late 1982 — it also won both the Academy Award and the Golden Globe for Best Original Song for a film in 1983. What we wouldn’t give for smokey-voiced Joe Cocker to serenade us with nonsense tales of eagles crying, all while being whisked away from our awful factory jobs!
28. Stop Draggin’ My Heart Around
Stevie Nicks With Tom Petty And The Heartbreakers
Although Stevie Nicks’ debut album, “Bella Donna,” featured more timeless singles like “Edge of Seventeen” and “Leather and Lace,” the Tom Petty collaboration “Stop Draggin’ my Heart Around” was the world’s first glimpse of the Fleetwood Mac singer as a solo artist. Produced by Petty and Jimmy Iovine, the rock track was even parodied by “Weird Al” Yankovic with the song “Stop Draggin’ My Car Around.”
27. No Air
Jordin Sparks with Chris Brown
Between the more self-affirming singles “Tattoo” and “One Step at a Time,” Jordin Sparks released this lilting duet with R&B star Chris Brown. A Grammy nominee for Best Pop Collaboration with vocals, “No Air” reached No. 3 on the Hot 100 and served as a precursor to Sparks’ emotionally wounded future single, “Battlefield.”
26. (I’ve Had) The Time Of My Life
Bill Medley & Jennifer Warnes
The Black Eyed Peas recently used the hook of Bill Medley and Jennifer Warnes’ duet for their single “The Time (Dirty Bit),” but the words “I’ve had the time of my life” will forever be tied to the 1987 film “Dirty Dancing.” The soft-rock hit closed out the Patrick Swayze-Jennifer Grey flick and won the 1987 Academy Award for Best Original Song.
25. Easy Lover
Philip Bailey & Phil Collins
Phil Bailey, the longtime member of Earth, Wind & Fire, and former Genesis drummer Phil Collins came together for this 80s pop confection off Bailey’s 1984 album “Chinese Wall.” Although the track was Bailey’s biggest hit by far, Collins scored again the following year with “Separate Lives,” his duet with Marilyn Martin.
24. You’re The One That I Want
John Travolta & Olivia Newton-John
The peppy collaboration between “Grease” stars Olivia Newton-John and John Travolta hit No. 1 on the Hot 100 in June 1978. “You’re The One That I Want,” along with the actors’ other duet “Summer Nights,” helped the soundtrack to the hit 1978 film become certified eight-times platinum, according to the RIAA.
23. Baby, Come To Me
Patti Austin & James Ingram
It’s one the greatest baby-making jams of all time, but “Baby Come to Me” was far from an immediate hit. When the Patti Austin & James Ingram duet was first released in 1982, it only made it to no. 73 on the Hot 100. But later that year, the track gained new exposure through its use on ABC soap opera “General Hospital.” In response to the newfound buzz, the song was re-released and climbed to No. 1 on both the Hot 100 and Adult Contemporary charts in early 1983.
Keith Sweat & Athena Cage
Keith Sweat, the king of new jack soul, conjured up an intense quiet storm when he teamed up with soulful chanteuse Athena Cage for this steamy R&B jam in 1996. The pair soared to no. 3 on the Hot 100, and sizzled at the top of the R&B chart for three hot weeks.
21. You Don’t Have To Be A Star (To Be In My Show)
Marilyn McCoo & Billy Davis, Jr.
Marilyn McCoo and Billy David Jr. didn’t have to struggle to find their chemistry in the studio. Not only had the pair been married for seven years when they recorded this 1976 R&B classic, they’d already spent a decade making beautiful music together as part of ’70s soul quintet The 5th Dimension. The pair’s romantic and musical bond paid off — the Grammy-winning track went to No. 1 on both the Billboard Hot 100 and Hot Soul Singles chart.
20. You Don’t Bring Me Flowers
Barbra Streisand & Neil Diamond
Some duets exude their magic even though their singers recorded their tracks separately. That was not only the case with this song, but it was never intended to be a duet to begin with. Diamond released his version months before Streisand’s. It wasn’t, however, until inventive WAKY Louisville, Ky., programmer Gary Guthrie created a mixed edit that audiences heard the now-classic dual version. Columbia then released the song with both superstars. In just six chart weeks, it became the third Hot 100 No. 1 for each.
19. Don’t Know Much
Linda Ronstadt feat. Aaron Neville
Though Ronstadt racked eight Hot 100 top 10s between 1975 and 1980, she didn’t reappear in the top tier until 1987 with the James Ingram duet “Somewhere Out There” (No. 2), from “An American Tail.” The ballad subsequently won the 1988 song of the year Grammy Award. For her next album, “Cry Like a Rainstorm, Howl Like the Wind,” Ronstadt included four duets with Neville. This first single not only reached No. 2 on the Hot 100, but it also topped Adult Contemporary for five weeks and won the 1990 Grammy for best pop performance by a duo or group with vocal.
18. Somethin’ Stupid
Nancy Sinatra & Frank Sinatra
The legendary Frank Sinatra claimed his final Billboard Hot 100 top 10 hit — and second No. 1 — thanks to an unlikely duet with his daughter Nancy Sinatra. The latter already had some hits under her belt — including the No. 1 “These Boots Are Made For Walkin'” in 1966 — so the “Stupid” pairing wasn’t simply a riding-the-coattails moment for the Chairman’s daughter. It is the only father-daughter duet to reach the top of the Hot 100, where it spent four weeks at the top.
17. The Way I Are
Timbaland & Keri Hilson
Super producer Timbaland called in a bunch of friends for his 2007 “Shock Value” album, including the rising star Keri Hilson, who guests on “The Way I Are.” Though the track didn’t hit No. 1, it did peak at No. 3 — for four non-consecutive weeks — and linger on the list for a healthy 38 weeks. “Way” was one of four Hot 100 hits from “Shock Value” — Timbo also claimed entries with “Give It To Me” (No. 1 for two weeks), “Release” (No. 91) and “Apologize” (No. 2).
16. Opposites Attract
Paula Abdul with The Wild Pair
Yes, duets with cartoon cats count. The song is perhaps best remembered for its video featuring the animated MC Skat Kat, voiced by the track’s featured act, the Wild Pair. “Opposites Attract” became the fourth and final Hot 100 No. 1 from Abdul’s debut album, “Forever Your Girl,” following “Straight Up,” the title cut and “Cold Hearted.” A year later, Mariah Carey banked her fourth leader from her eponymous debut set, but no other artists in the chart’s history have accomplished such out-of-the-gate domination.
15. Empire State of Mind
Jay-Z + Alicia Keys
It’s an Empire State Building-tall order to create a Big Apple anthem when there’s already Frank Sinatra’s “New York, New York” (and Billy Joel’s “New York State of Mind”). All the more impressive, then, that Jay-Z and Keys ruled the Hot 100 for five weeks with their modern Gotham theme. A Keys solo piano version reached No. 55 and the “Glee” cast opened its second season by performing its rendition, in honor of this year’s nationals show choir finals taking place in the “concrete jungle where dreams are made, oh.” (It peaked at No. 21). Our (biased) favorite line from the song? Jay-Z’s astute observation, “now I live on Billboard”!
Nelly Furtado & Timbaland
Suggesting that “Promiscuous” was a jarring change of pace for Nelly Furtado would be an understatement. As the lead single from her Timbaland-produced “Loose” album in 2006, the sexy, thumpy number was a far cry from the more earnest, quirky singles of her first two albums — including “I’m Like a Bird” and “Turn Off The Light.” But sexy clearly worked, as the cheeky “Promiscuous” tune spent eight weeks lodged in the No. 1 slot. It was the first of two toppers from “Loose” — she later returned with “Say It Right.”
Peaches & Herb
The only good thing about breaking up is that it opens the door for making up — a topic that R&B duo Peaches & Herb explored in their 1979 hit “Reunited.” The slow-burning jam became a crossover smash, topping both the Hot 100 and R&B Singles charts. The song has also inspired several cover versions, including one by rock band Faith No More, who performed it during their 2009-10 reunion tour, and German star David Hasselhoff, who sung it at the fall of the Berlin Wall in 1989.
12. Separate Lives
Phil Collins and Marilyn Martin
Before there was “Black Swan,” the ’80s gave us the elegant dance film “White Nights,” starring Russian ballet icon Mikhail Baryshnikov, as well as Gregory Hines, Helen Mirren and Isabella Rossellini. The movie is also remembered for its hit soundtrack, which yielded two Hot 100 No. 1s: Lionel Richie’s Oscar-winning “Say You, Say Me” and this intimate ballad, written by Stephen Bishop (“It Might Be You”). The song became Martin’s only topper and the fourth of Collins’ seven solo leaders.
11. On My Own
Patti LaBelle & Michael McDonald
While as the leaders of their respective groups Labelle and the Doobie Brothers, LaBelle and McDonald earned No. 1 Billboard Hot 100 singles, neither had a solo topper until this 1986 duet. Interestingly, the two singers hadn’t met until well after the song was recorded and was scaling the chart — as the single was put together on different coasts in different studios. As Fred Bronson notes in his “Billboard Book of Number One Hits,” “As ‘On My Own’ went to No. 1 on the Billboard Hot 100, LaBelle and McDonald met for the first time — at NBC Studios in Burbank (Calif.), where they performed the song on ‘The Tonight Show Starring Johnny Carson.'”
10. Don’t Go Breaking My Heart
Elton John & Kiki Dee
John has recorded so many hit duets he even released an album entitled “Duets,” which peaked at No. 25 on the Billboard 200 in 1993. Following his classic pairing with Dee, Elton graced the Hot 100 with the likes of Aretha Franklin, George Michael (their “Don’t Let the Sun Go Down on Me” hit No. 1 in 1992), LeAnn Rimes and RuPaul(!), whose dance remake of this song, from “Duets,” dented the chart (No. 92) in 1994. John’s current album? The collaborative “The Union,” with Leon Russell, which stands as John’s top-charting set (No. 3) on the Billboard 200 since 1976.
9. Islands In The Stream
Kenny Rogers with Dolly Parton
Some 30 years ago, star power didn’t shine much brighter than that of Rogers and Parton, who charted a combined 22 No. 1s on Country Songs in the ’80s. Add that this song was written by the Bee Gees and it’s no surprise that it topped the Hot 100 for two weeks, as well as Country Songs and Adult Contemporary. In 1998, Pras Michel borrowed its melody for the chorus of “Ghetto Supastar (That Is What You Are).” The reinvention, featuring Ol’ Dirty Bastard and Mya, hit No. 15 on the Hot 100 and No. 8 on R&B/Hip-Hop Songs.
8. Baby Boy
Beyonce & Sean Paul
Whether on her own (“Irreplaceable,” “Single Ladies (Put a Ring on It)”); in pairings (“Beautiful Liar,” with Shakira, “Telephone,” with Lady Gaga); or, in the trio Destiny’s Child (“Bills, Bills, Bills,” “Say My Name”), Beyonce = Hot 100 hit-making. This duet marked the second of her five No. 1s since 2003 as a solo artist, following four toppers in Destiny’s Child in 1999-2001. Paul capped the Hot 100 once before this leader, with “Get Busy” (three weeks, 2003), and once after, with “Temperature” (one week, 2006).
7. My Boo
Usher and Alicia Keys
Not to be confused with the 1996 hit of the same name by Ghost Town DJs, this ode to having a boyfriend or girlfriend “that will always have your heart” was tailor made for success because of the team of R&B superstars behind it. Not only does the track find Keys’ golden tones mingling with Ushers, the was the track co-written by Keys, Usher and Jermaine Dupri with Manuel Seal and Adonis Shropshire. Little wonder, then, that it rocketed to No. 1 and stayed there for six weeks.
6. I’m Real
Jennifer Lopez & Ja Rule
Here’s another of the four songs that J.Lo, with assistance from Ja Rule, took to No. 1 on the Hot 100 before she joined the judges panel on TV’s No. 1-rated show, “American Idol.” Complementing her new night job, Lopez (previously at No. 36 on this ranking) has recently released the single “On the Floor,” featuring Pitbull. The track marks her first appearance on Billboard’s Dance Airplay chart (where it debuted last week at No. 23) since 2007.
Nelly & Kelly Rowland
If you’re a member of any group where there is someone who is ostensibly the lead singer — and you aren’t them — it isn’t easy to break out on your own. So for Destiny’s Child’s Kelly Rowland, her first single away from the group was an event. An event that could either turn into a footnote or a smash. And what a smash it was. Her “Dilemma” duet with Nelly notched a stunning 10-week run at No. 1 on the Billboard Hot 100, cementing Rowland as not just a backing vocalist to Beyonce, but a solo star in her own right.
4. Ebony And Ivory
Paul McCartney and Stevie Wonder
Recorded for Paul McCartney’s “Tug Of War” album, the duet — which spent seven weeks atop the Billboard Hot 100 — is the longest-running solo No. 1 for either McCartney or his duet partner Stevie Wonder. “Ebony and Ivory” works as a sort of ultimate “can’t we get along?” song, with the lyric: “Ebony and ivory live together in perfect harmony / side by side on my piano keyboard, oh lord why don’t we?”
3. The Boy Is Mine
Brandy & Monica
This 1998 duet had all the makings of a smash single. First, it paired up rising then-teen female R&B stars Brandy and Monica — each of whom had notched four top 10 Billboard Hot 100 hits on their own, but not yet a No. 1. Second, there were rumors swirling that the two ladies weren’t exactly on friendly terms. Third, the lyrical content of the song was all about fighting over a man — perfect fodder for alleged rivals to sing about. The result? A No. 1 that lasted for 13 weeks at the top — at the time, one of only seven singles in the chart’s history to spend that long at No. 1.
2. Say Say Say
Paul McCartney and Michael Jackson
Just seeing the words “Michael Jackson” and “Paul McCartney” placed next to each other would have sent chills up any music fan’s spine back in 1983, when “Say, Say, Say” was released. The super duo’s hit spent six weeks atop the Billboard Hot 100 and was the second of two duets from the pair, following “The Girl Is Mine” (No. 2 on Jan. 8, 1983). The stars drifted apart after 1985, when Jackson purchased the massive ATV catalog of songs (which included the majority of the Beatles’ catalog). McCartney was later cool to Jackson, but after the latter’s passing in 2009, he issued a statement about the King of Pop: “I feel privileged to have hung out and worked with Michael. He was a massively talented boy man with a gentle soul. His music will be remembered forever and my memories of our time together will be happy ones.”
1. Endless Love
Diana Ross & Lionel Richie
Diana Ross & Lionel Richie’s “Endless Love” crowns our list of the top duets of all time — and with good reason. It’s not only the biggest No. 1 hit for either artist (it spent nine weeks at the top), but also clung to the chart for an amazing 27 weeks — a lengthy run for a single back in 1981. Richie wrote the music and lyrics for the soundtrack tune from the Brooke Shields movie of the same name, and recruited diva Ross to accompany him on the song. “Endless” almost returned to the Hot 100 perch nearly 13 years later, when Luther Vandross and Mariah Carey’s cover stalled at No. 2 on Oct. 1, 1994.