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. (For all of the details on how this chart was compiled, scroll to the bottom of this page.)
1.
Endless Love
Diana Ross & Lionel Richie
1981
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.
2.
Say Say Say
Paul McCartney and Michael Jackson
1983
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."
3.
The Boy Is Mine
Brandy & Monica
1998
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.
4.
Ebony And Ivory
Paul McCartney and Stevie Wonder
1982
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?"
5.
Dilemma
Nelly & Kelly Rowland
2002
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 Beyoncé, but a solo star in her own right.
6.
I'm Real
Jennifer Lopez & Ja Rule
2001
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.
7.
My Boo
Usher and Alicia Keys
2004
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.
8.
Baby Boy
Beyoncé & Sean Paul
2003
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"), Beyoncé = 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).
9.
Islands In The Stream
Kenny Rogers with Dolly Parton
1983
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.
10.
Don't Go Breaking My Heart
Elton John & Kiki Dee
1976
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.
13.
Reunited
Peaches & Herb
1979
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.
14.
Promiscuous
Nelly Furtado & Timbaland
2006
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."
15.
Empire State of Mind
Jay-Z + Alicia Keys
2009
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"!
16.
Opposites Attract
Paula Abdul with The Wild Pair
1988
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
17.
The Way I Are
Timbaland & Keri Hilson
2007
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).
27.
No Air
Jordin Sparks with Chris Brown
2008
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."
34.
All I Have
Jennifer Lopez & LL Cool J
2003
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?).
http://www.billboard.com/features/th...05032672.story
"Ebony & Ivory" is so corny but has a great message. 
