Iconic Duos Reunited: Santana & Rob Thomas, and Other Hit Collaborators Who Tried to Recapture the Magic

Written by on August 21, 2021

When Santana hooked up with Rob Thomas for the first time in 1999, the San Francisco classic rock band led by guitarist Carlos Santana hadn’t had a top 10 hit in a couple decades, and Thomas had just risen to fame with the first few hits from his band Matchbox Twenty. But “Smooth,” the lead single from Santana’s comeback album Supernatural, was a game-changer for both of them: With 12 weeks spent at No. 1 on the Billboard Hot 100, it was one of the chart’s biggest hits of all time, and ended up winning three Grammys.

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While Santana continued collaborating on hits with younger artists after “Smooth,” and Rob Thomas had continued success with Matchbox Twenty (as well as a moderately successful solo career), the dynamic duo didn’t record together again for the next 22 years. But on August 18th, Santana released “Move,” the lead single from the forthcoming Blessings & Miracles, another summery Latin rock single featuring Rob Thomas, as well as the band American Authors. While it’s hard to imagine “Move” equalling the enormous popularity of “Smooth,” it could once again prove to be a major career bump for both Santana and Thomas.

Earlier this month, another pair of major stars released their first collaboration since the ‘90s. Nas released “If I Ruled the World” featuring Lauryn Hill to launch his biggest album, It Was Written, in 1996. The song reached No. 53 and gave Hill her first Hot 100 hit as a solo artist after rising to fame as a member of The Fugees. Nas’s latest album, Kings Disease II, features Hill on “Nobody,” which has been widely hailed as one of her best verses in the decades since her lone solo studio album, 1998’s The Miseducation of Lauryn Hill. “Nobody” debuted at No. 42 on the R&B/Hip-Hop Songs chart, and King’s Disease II peaked at No. 3 on the Billboard 200.

Some duet partners make one hit together and that’s it — like Patti LaBelle and Michael McDonald’s No. 1 hit “On My Own.” Other pairs of closely associated solo artists work together over and over on songs large and small, like Marvin Gaye and Tammi Terrell, or even Lil Wayne and Drake. But some duos make such a big hit together that they can’t help but link back up from time to time, to try to see if lightening can strike twice. Here are 10 hitmaking teams who reunited at least once after making a smash together.

Elton John and Kiki Dee

British soul singer Kiki Dee began releasing music in the mid-‘60s and scored her first Hot 100 hit in 1971. But her career ascended to new heights when she signed to Elton John’s Rocket label, and 1974’s “I’ve Got the Music in Me” peaked at No. 12. Her most enduring track, of course, was a 1976 duet with her boss, a Motown pastiche that Elton John originally planned to sing with Dusty Springfield. “Don’t Go Breaking My Heart” was Elton John’s last Hot 100 chart-topper of the ‘70s, capping his first run of hits. Dee and John later reunited for two covers: A 1981 version of the Four Tops’ “Loving You is Sweeter Than Ever” missed the charts, but a rendition of Cole Porter’s “True Love” from John’s 1993 Duets album was a hit, reaching No. 56 on the Hot 100 and No. 2 on the UK Singles Chart.

Stevie Nicks and Tom Petty & The Heartbreakers

When Stevie Nicks took a break from Fleetwood Mac to record her first solo album, 1981’s Bella Donna, she surrounded herself with fellow rock stars like Tom Petty and Don Henley, with whom she recorded duets for the album’s first two singles. The first song Petty wrote for Nicks, “Insider,” wound up on his and the Heartbreakers’ Hard Promises album with Nicks singing backup, while Nicks ultimately chose “Stop Draggin’ My Heart Around” for her album. The song peaked at No. 3, the biggest Hot 100 hit of Petty’s career, and Nicks’s biggest hit outside Fleetwood Mac. Nicks continued collaborating with Petty and members of the Heartbreakers for years, with two more duets later in the decade. 1983’s “I Will Run to You” was a minor radio hit, reaching No. 35 on the Mainstream Rock Songs chart, while Petty’s 1985 live cover of Jackie DeShannon’s “Needles and Pins” with Nicks hit No. 37 on the Hot 100.

Paul McCartney and Michael Jackson

Michael Jackson’s first collaboration with Paul McCartney was “The Girl Is Mine,” the famously goofy and slight duet in which the two legends play romantic rivals that was the lead single to Jackson’s blockbuster Thriller. The song reached No. 2 on the Hot 100 but gave little sense of the kind of cutting edge pop elsewhere on the album that would soon push it to unprecedented sales. A year later, they released another collaboration that was actually recorded first, the superior “Say Say Say,” for McCartney’s Pipes of Peace album, and the single topped the Hot 100. But the superstars’ friendship soured in 1985, when Jackson outbid McCartney for the publishing rights to the Beatles’ song catalog.

Method Man and Mary J. Blige

Updating an iconic Marvin Gaye and Tammi Terrell duet for the hip-hop soul era, “I’ll Be There for You/You’re All I Need to Get By” from Method Man’s solo debut Tical peaked at No. 3 on the Hot 100 in 1995. It was the biggest hit of the Wu-Tang Clan rapper’s career, and Mary J. Blige’s highest chart peak at the time. Eight years later, they reunited for the lead single to Blige’s 2003 album Love & Life, and “Love @ First Sight” reached No. 22 on the chart.

Brandy and Monica

The title coyly recalled Michael Jackson and Paul McCartney’s “The Girl is Mine,” but Brandy and Monica’s “The Boy is Mine” was an even bigger smash, the first Hot 100 No. 1 for both R&B teen queens, and the lead single to each singer’s biggest album in 1998. Rumors of a real life rivalry between Brandy and Monica persisted before and after the song’s success. But they reunited in 2012 for “It All Belongs To Me,” a Rico Love-produced single from Monica’s New Life album that missed the Hot 100 but peaked at No. 23 on the R&B/Hip-Hop Songs chart. And in September 2020, Brandy and Monica broke records for the most watched Verzuz webcast when they reteamed for the song battle series.

Nelly and Kelly Rowland

Hitting No. 1 for 10 weeks in 2002, “Dilemma” was the longest-reigning Hot 100 smash of Nelly’s career, and Kelly Rowland’s first chart-topper outside Destiny’s Child. And like Brandy and Monica, Nelly and Kelly reunited a decade later for a Rico Love-produced song: “Gone” from Nelly’s 2010 album 5.0 was originally titled “Dilemma Pt. 2,” before he decided against framing the song as a sequel. It also missed the Hot 100, peaking at No. 59 on the R&B/Hip-Hop Songs chart.

Alan Jackson and Jimmy Buffett

The first time Alan Jackson sang with Jimmy Buffett, they remade Buffett’s 1977 signature song “Margaritaville” for Jackson’s 1999 covers album Under the Influence, but the track wasn’t released as a single. Four years later, however, their duet “It’s Five O’Clock Somewhere” topped the Country Songs chart for eight weeks. Hitting No. 17, it was the biggest Hot 100 hit of Jackson’s career, and Buffett’s biggest hit since the original “Margaritaville.” Its success influenced the country direction of Buffett’s next album, 2004’s License To Chill, which featured two more collaborations with Jackson. Their duet “Boats to Build” wasn’t released as a single, but a cover of Hank Williams’s “Hey, Good Lookin’” that featured Jackson along with Clint Black, Kenny Chesney, Toby Keith and George Strait hit No. 63 on the Hot 100.

Usher, Ludacris and Lil Jon

When Usher’s 2004 single “Yeah!” topped the Hot 100 for 12 weeks, he formed a memorable trio of hitmakers with the song’s guest rapper Ludacris and producer and hypeman Lil Jon. While there are several tracks with two of the three artists, the trio have worked as a team just a couple more times. “Lovers & Friends” from Lil Jon’s Crunk Juice album peaked at No. 3 in 2005. But their 2020 reunion “SexBeat” was a miss, reaching just No. 44 on the R&B/Hip-Hop Airplay chart.

Eminem and Rihanna

After Eminem’s “Love the Way You Lie” featuring Rihanna topped the Hot 100 for seven weeks in 2010, they reunited for two Rih album cuts: the sequel “Love the Way You Lie (Part II)” on 2010’s Loud, and “Numb” on 2012’s Unapologetic. But they returned to the Hot 100’s peak for four more weeks in 2013 and 2014 with“The Monster” from Em’s The Marshall Mathers LP 2. However, the duo have not worked together since 2019, when an unreleased older track leaked that featured Eminem lyrics making light of Chris Brown’s 2009 assault of Rihanna.

Ariana Grande and Mac Miller

When Mac Miller appeared on Ariana Grande’s breakthrough hit “The Way” in 2013, it peaked at No. 9 on the Hot 100 and became the first top 10 hit for both artists, who were not yet a couple at the time. But over the next few years, the two wrote several songs about each other and their on-again off-again relationship. And they collaborated once more before Miller’s 2018 death, when Grande appeared on “My Favorite Part” from his 2016 album The Divine Feminine.


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