20 Best Love Songs By Real-Life Couples

Whether it’s a chart-topping pop pair, an R&B/hip-hop power couple or a country king and queen, it’s the natural inclination for a musically inclined romantic couple to collaborate – or for a platonic pair of singer to find love during heated recording sessions. In honor of Valentine’s Day, the Billboard staff has hand-picked the 20 best duets by real-life musical couples. Some of the relationships themselves may be over and done with, but the beautiful music these iconic couples made together will live on forever.

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PHOTOS: Pop Star Hookups & Breakups
40 Biggest Duets Ever | 30 Biggest Break-Up Songs

  1. 20

    “Must Be Love” - Cassie feat. Diddy Mainstream R&B/Hip-Hop Chart Peak: 38 (July 4, 2009)

    A Bad Boy turned good? That's what happened when rap star/mogul Diddy started dating R&B singer Cassie in 2007, despite their 16-year age difference. In 2009, they collaborated on the single "Must Be Love,” which topped out at No. 38, Mainstream R&B/Hip-Hop chart. The couple started engagement rumors in early February 2014 when Diddy posted a photo of a humongous diamond ring on Instagram with the caption "Baby do you like it?" Another picture from that night, posted by singer Keyshia Cole, might show Cassie donning the rock on her left hand, though nobody has confirmed the commitment.

  2. 19

    “Where You Are” - Jessica Simpson & Nick Lachey Pop Songs Chart Peak: 22 (April 15, 2000)

    The couple started dating in 1999 when Simpson was in her late teens and Lachey, most famously of boy band 98 Degrees, was in his mid 20s. Soon after, they recorded the duet "Where Are You" for her first album, "Sweet Kisses." “Where You Are” peaked at no. 22 on the Pop Songs chart, but it wasn’t nearly as successful as their reality series. After they married in 2002, MTV's ‘Newlyweds: Nick and Jessica’ depicted their life, and Simpson's frequent ditzy moments, until 2005, the same year they announced they were getting divorced. Simpson now has two children with former NFL player Eric Johnson, while Lachey has a child with his second wife, former MTV VJ Vanessa Minnillo.

  3. 18

    “Whats My Name”- Papoose & Remy Ma (2013)

    The New York rappers announced their engagement in 2008, just before Remy Ma was set to go to jail for her involvement in a shooting outside a New York City club (Remy allegedly shot another woman, but was convicted of assault, weapon possession and attempted coercion). The pair married in May ‘08 while Ma was in prison. During her incarceration, she found time to collaborate with her husband on 2013's "What's My Name," a song off his album ‘The Nacirema Dream,’ which peaked at no. 97 on the Billboard 200 chart. The pair is set to reunite in July 2014, when Ma is scheduled to be released from prison.

  4. 17

    “Summit” - Skrillex & Ellie Goulding Hot Dance/Electronic Songs Chart Peak: 18 (Jan. 26, 2013)

    The EDM star and British songstress teamed up in 2011 to record the chilled-out "Summit" for Skrillex's "Bangarang" EP. He and Goulding started dating a couple months into 2012, but by October, they had called it quits due the strains of the long-distance relationship. “Summit” peaked at no. 18 on the Hot Dance/ Electronic Songs chart, while ‘Bangarang’ topped the Dance/Electronic chart, hit No. 14 on the Billboard 200, and won a best dance/ electronica album Grammy in 2013.

  5. 16

    "Vertigo" - Jason Derulo & Jordin Sparks (2013)

    Derulo started dating the former "American Idol" winner in 2012, and they collaborated on the song "Vertigo" from his 2013 album "Tattoos." However, it was their performance in his video for the single "Marry Me" that got the most attention. In it, Derulo is seen buying a ring and proposing to Sparks; his grandparents play the older version of the couple at the video's end.

  6. 15

    "In Another's Eyes" - Trisha Yearwood & Garth Brooks Hot Country Songs Chart Peak: 2 (Nov. 9, 1997)

    In the late '90s, both Brooks and Yearwood were among the top country artists in the world. His seventh album, appropriately titled "Sevens," featured his first-ever duet, "In Another's Eyes," with Yearwood's soaring voice helping to propel to No. 2 on the Hot Country Songs chart and win the Grammy for best country collaboration with vocals in 1997. Sparks flew between the two both in and out of the studio; they began dating after Brooks' 2000 divorce and married in 2005.

  7. 14

    “Let Me Go” - Avril Lavigne & Chad Kroeger Adult Pop Songs Chart Peak: 20 (Jan. 4, 2014)

    The "Sk8er Boi" singer and Nickelback frontman teamed up to write songs for her self-titled fifth album in 2012. They started dating that July and got engaged a month later. Kroeger and Lavigne married on July 1, 2013, exactly four months before her eponymous fifth album was released. The power couple's collaborations propelled "Avril Lavigne" to No. 5 on the Billboard 200, while their collaborative single “Let Me Go” peaked at 20 on the Adult Pop Songs chart.

  8. 13

    “Something in Common” - Bobby Brown & Whitney Houston Pop Songs Chart Peak: 12 (Dec. 4, 1993)

    Co-written and produced by Teddy Riley, "Something in Common" was originally recorded for Brown's album ‘Bobby’ in 1992, the same year the couple wed. The song reached no. 12 on the Pop Songs chart in1993, but the turmoil of their drama-fueled marriage led to more time in the tabloids than on the charts for the rocky R&B pair. The couple eventually divorced in 2007, five years before Houston passed away.

  9. 12

    “Falling Slowly" - The Swell Season Digital Songs Chart Peak: 20 (March 15, 2008)

    While filming the hit indie film "Once," The Swell Season's Glen Hansard and Marketa Irglova wrote the movie's standout song, "Falling Slowly." When the 2007 film gained international attention, 37-year-old Hansard and 19-year-old Irglova began a relationship during a promotional trip, and "Falling Slowly" went on to win the Oscar for Best Original Song. They broke up in 2009 before they released the Swell Season's third album, ‘Strict Joy,’ and Swell Season went on hiatus in 2011.

  10. 11

    “Body Party” - Ciara feat. Future Mainstream R&B/Hip-Hop Chart Peak: 1 for three weeks (July 13, 2013)

    The R&B singer and auto-tune-loving rapper revealed they were dating in January 2013, two months before the release of her single "Body Party." Besides co-writing the hit alongside Mike WiLL Made It, Future contributed ooh's and ad-libs to the track, and would later appear alongside B.o.B. on its official remix. The sexy song topped the Mainstream R&B/Hip-Hop songs chart for 3 weeks. Ciara and Future got engaged in October 2013 and are expecting their first child sometime this year.

    NEXT: 10-1

  11. 10

    “Who You Love” - John Mayer & Katy Perry Adult Pop Songs Chart Peak: 18 (Nov. 23, 2013)

    Perry started dating Mayer after the July 2012 dissolution of her marriage to actor Russell Brand. They co-wrote "Who You Love," a modern take on classic easy-listening tracks, for his sixth album, ‘Paradise Valley,’ and filmed a video that featured them riding a mechanical bull. The track went to no. 48 on the Hot 100, while Mayer’s LP went all the way to no. 2.

  12. 9

    “Love Will Keep Us Together” - Captain & Tenille Hot 100 Chart Peak: 1 for four weeks (June 21, 1975)

    Former Beach Boys keyboardists "Captain" Daryl Dragon and Toni Tennille married on Nov. 11 1974, and became a soft-pop smash six months later with their peppy cover of Neil Sedaka's "Love Will Keep Us Together.” The song topped the Easy Listening and Hot 100 charts, became the best-selling single of '75, and won the record of the year Grammy. After 39 years of marriage, Tennille shockingly filed for divorce in January 2014, with the blindsided Captain reportedly not knowing it was coming until he was served the papers.

  13. 8

    "It's Your Love" - Tim McGraw & Faith Hill Hot Country Songs Chart Peak: 1 for six weeks (June 7, 1997)

    A year after meeting on tour and marrying in 1996, McGraw and Hill recorded "It's Your Love," a song written by Stephon Smith. The song topped the Hot Country Songs chart for six weeks, and peaked at no. 7 on the Hot 100. The single won four ACM awards, including one for its video, in which Hill is pregnant with the couple's first daughter, Gracie. They've since had two more daughters, and won a Grammy in 2001 for their duet "Let's Make Love."

  14. 7

    “Proud Mary” - Ike & Tina Turner Hot 100 Chart Peak: 4 (March 27, 1971)

    Ike Turner met Anna Mae Bullock, an aspiring singer in her late teens, at a St. Louis club in 1957 and was so enamored with her talents that she soon moved in with him. They founded the Ike and Tina Turner Revue (Ike allegedly asked her to change her name so she could be replaced if she ever left) and they married in 1962. Following years of R&B-chart toppers, they hit it biggest in 1971 with a cover of Creedence Clearwater Revival's "Proud Mary,” which peaked at no.4 on the Hot 100. After years of physical abuse, Tina eventually fled from Ike and they divorced in 1976, with Tina dropping all her monetary claims and retaining only her stage name. Ike experienced highs and lows in both his personal and professional life before dying on a cocaine overdose in 2007.

  15. 6

    “No Me Ames” - Jennifer Lopez & Marc Anthony Hot Latin Songs Chart Peak: 1 for seven weeks (June 26, 1999)

    Lopez and Anthony met by chance in a recording studio while she was working on her debut album, 1999's "On the 6." After Anthony asked her to be in one of his videos, she agreed on the condition that he record a duet with her. They chose a Spanish translation of the Italian song "Non Amarmi,” which topped the Hot Latin Songs chart for seven weeks that year. After maintaining their long-time friendship (which involved a brief period of dating in the late-‘90s), Lopez and Anthony married in 2004, toured together in 2007, had twins – a girl and a boy – in 2008 … and sadly divorced in 2012.

  16. 5

    “Birthday Cake” - Rihanna feat. Chris Brown Mainstream R&B/Hip-Hop Chart Peak: 1 for three weeks (May 19, 2012)

    Just over three years after Chris Brown assaulted Rihanna the night before the 2009 Grammys, the on-and-off flames rekindled their relationship and collaborated on a controversial remix of her ‘Talk That Talk’ track "Birthday Cake." Released on Rihanna's 24th birthday in 2012, the track peaked at no. 2 on the R&B/Hip-Hop charts. Later that year, she courted more controversy by naming her seventh album Unapologetic,’ which featured another duet with Brown, titled "Nobody's Business." The pair split again in 2013.

     

     

  17. 4

    “Jackson” - Johnny Cash & June Carter Cash Hot Country Songs Chart Peak: 2 (May 6, 1967)

    Cash met Carter backstage at the Grand Ole Opry in 1955, and they recorded a duet of the Billy Edd Wheeler and Jerry Leiber song "Jackson" 12 years later. The song hit no. 2 on the Hot Country Songs chart (Nancy Sinatra and Lee Hazelwood's version, released that same year, peaked at 14 on the Hot 100) and won them a Grammy for best country & western performance duet, trio or group in 1968. That year, Cash proposed to Carter onstage at a London, Ontario performance and they remained together until her death in May 2003. He died four months later.

  18. 3

    “Solid” - Ashford & Simpson Hot R&B/Hip-Hop Songs Chart Peak: 1 for three weeks (Dec. 1, 1984)

    By the time they married in 1974, Nickolas Ashford and Valerie Simpson already had an amazingly successful career as a songwriting duo, with credits such as Marvin Gaye and Tammi Terrel's "Ain't No Mountain High Enough" and Ray Charles' "Let's Go Get Stoned." In 1984, just a few years after penning "I'm Every Woman" for Chaka Khan, the couple kept one hit for themselves, the relationship-affirming "Solid," which they remade in 2009 as "Solid (As Barack)" for President Obama. Ashford died from throat cancer in 2011, survived by his wife and two daughters.

  19. 2

    “I Got You Babe” - Sonny & Cher Hot 100 Chart Peak: 1 for three weeks (Aug. 14, 1965)

    Salvatore Bono met the younger Cherilyn Sarkisian in L.A. while he was working as an assistant to Phil Spector. Their romance led to session recording work and eventually their own releases as Sonny and Cher. Their biggest hit, 1965's "I Got You Babe," is a classic about young love, and it spent three weeks at no.1. The couple divorced in 1975, but reunited to perform "I Got You Babe" on ‘Late Night With David Letterman’ in 1987. Cher paid her final respects to Bono in 1998 during a eulogy she delivered at his funeral. “He created Sonny & Cher,” she said then. “He knew what was right for us.”

  20. 1

    “Crazy in Love” - Jay Z feat. Beyonce Hot 100 Chart Peak: 1 for eight weeks (July 12, 2003)

    The fiercely private Bey and Jay reportedly started dating after their first collaboration, 2002’s "'03 Bonnie & Clyde," which peaked at no. 4 on the Hot 100. In May 2003, they took their budding romance to new musical heights with "Crazy in Love." (Jay improvised his verse at a 3 a.m. recording session, the night before Beyonce's debut solo album, ‘Dangerously in Love,’ was due to her label.) Eleven years after “Crazy” topped the Hot 100, the now-married couple’s hit-making streak continues; “Drunk in Love,” their collab from Beyonce’s 2013 self-titled album, hit no. 2 on the Hot 100 in February 2014.

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    Top 50 'Love' Songs of All Time
    PHOTOS: Pop Star Hookups & Breakups
    40 Biggest Duets Ever | 30 Biggest Break-Up Songs