- Kevin Mazur/Getty Images
- Post Malone’s third album, “Hollywood’s Bleeding,” was released on September 6, and contains a surprising but enjoyable collaboration between Malone, Travis Scott, and former Black Sabbath front man Ozzy Osbourne.
- This isn’t the first time generations have collided to make great music.
- Tony Bennett and Lady Gaga collaborated on the 2014 album “Cheek to Cheek,” which confused some Gaga fans.
- Sting and Shaggy released a collaborative album in 2018, called “44/876.”
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As time goes by, certain musicians transcend their status as a mere pop star, and are gilded in music history forever as legends. You know them – Paul McCartney, Sting, Madonna – but for some it’s been years since their music has hit the top of the charts.
That’s where our current pop stars come in. All of these collaborations are notable in that they might not make sense on paper, like combining Young Thug and Elton John, but they actually sound pretty good, and they help a younger generation learn more about pop music past.
Here are 13 of the most unexpected yet delightful collaborations between musical legends and pop stars.
Ozzy Osbourne appears alongside Travis Scott on Post Malone’s new album.
Malone’s latest album, “Hollywood’s Bleeding,” dropped on September 6, and was filled with plenty of collaborations, but none as mystifying as his team-up with heavy metal icon Osbourne and fellow rapper Scott.
Ariana Grande and Stevie Wonder sang “Faith” together, which was released for the 2016 film “Sing.”
“Faith” was released in November 2016 as the first single from the soundtrack for musical film “Sing.” It was nominated for the Best Original Song at the Golden Globes, though it lost to “City of Stars” from “La La Land.”
The year prior, Grande and Babyface covered “Signed, Sealed, Delivered, I’m Yours” at a Grammys tribute.
Young Thug used a sample of an Elton John song after the legend expressed his love for the rapper.
Cut to September 2018, when the song “High,” which used an a capella sample of John’s hit “Rocket Man,” leaked onto the internet. The response to the song was so positive it was officially released on Thug’s EP, “On the Rvn,” once John approved the use of his vocals.
In fact, when the song leaked John called Thug to thank him for including him, according to Rolling Stone. “He called – I wish I’d recorded the conversation – [and] he’s like, ‘I’m so honored that you would do that, it’s so flattering,'” said the rapper’s A&R, Geoff Ogunlesi, “Then getting [the sample] cleared was no problem.”
Tony Bennett and Lady Gaga collaborated on the 2014 album “Cheek to Cheek,” which confused some Gaga fans.
- Kevin Mazur/Getty Images
In 2014, Bennett was 88 years old, while Gaga was 50 years his junior at 28. She was also mainly known for her larger-than-life persona that included dresses made out of meat and songs like “Telephone” and “Alejandro.” It wasn’t a combo that immediately made sense.
But, somehow, their 2014 classic album “Cheek to Cheek” works. Until then, a casual listener would not have known that Gaga possessed a beautiful voice that was well-suited to jazz standards like “Anything Goes” and “It Don’t Mean a Thing (If It Ain’t Got That Swing).”
In 2018, Opera legend Andrea Bocelli released the song “If Only” with reigning Best New Artist Dua Lipa.
“If Only” was Bocelli’s first single in 14 years, and appeared on his album “Sí,” which was his first album of original material in 14 years as well, after his 2004 album “Andrea.” In total, he’s released 15 albums and nine complete operas over his 37-year career.
Dua Lipa, on other hand, is an almost brand-new artist, but unquestionably a pop star. She released her debut album in 2017, and has earned six Hot 100 songs, as well as the Best New Artist Grammy in 2019.
“If Only” itself didn’t chart, but “Sí” made its way to the top of the Billboard 200.
Ed Sheeran also joined forces with Andrea Bocelli for a new version of his song “Perfect,” called “Perfect Symphony,” as well as for “Amo Soltanto Te,” which appeared on Bocelli’s album “Sí.”
First, the two crooners collaborated on “Perfect Symphony” in December 2017, which was a fully orchestrated version of Sheeran’s song “Perfect.” The new version had Bocelli and Sheeran partially singing in Italian. It hit No. 1 in three countries.
The two worked together again for a duet on Bocelli’s album “Sí.” The song, “Amo Soltanto Te,” which translates to “I Only Love You,” is sung entirely in Italian, and had Sheeran fans around the world swooning.
In 2008, Madonna, Justin Timberlake, and Timbaland collaborated on “4 Minutes,” which was on Madonna’s 11th album, “Hard Candy.”
- Kevin Mazur/Getty Images
The song “4 Minutes” was released on Madonna’s 11th album, “Hard Candy” in 2008, right at the height of Timberlake’s “FutureSex/LoveSounds” mania. In 2007 alone, he released singles “LoveStoned,” “Summer Love,” and “Until the End of Time.”
Timbaland was also having a good run. In 2007, he released three top five singles: “Give It to Me” (which also featured Timberlake), “The Way I Are,” and “Apologize.”
Justin Bieber released “All I Want for Christmas Is You (SuperFestive!)” on his 2011 Christmas album “Under the Mistletoe,” complete with a feature from Mariah Carey.
Carey, unquestionably, is still a pop star, but she has most certainly crossed over into legend territory. Until this summer and “Old Town Road,” she held the record for longest-running No. 1 song, along with fellow legends Boyz II Men.
Carey’s “All I Want for Christmas Is You,” which was originally released in 1994, is one of the most recent additions to the Christmas classics canon – so, of course, Bieber had to include it on his 2011 album “Under the Mistletoe.” But instead of just covering it, he re-recorded the song with the Elusive Chanteuse herself, and co-starred in the music video with her.
“Under the Mistletoe” debuted at No. 1 on the Billboard 200, which made it the first Christmas album sung by a male artist to debut at No. 1.
Justin Bieber also collaborated with iconic boy band Boyz II Men for original song “Fa La La” on his 2011 Christmas album.
- YouTube/Justin Bieber
Boyz II Men, the other half of the former longest-running No. 1 of all time, also collaborated with Bieber for a song on his Christmas album. “Under the Mistletoe” was an original song, not a cover.
Boyz II Men became the third artist ever to replace themselves as No. 1 on the Billboard Hot 100, when “On Bended Knee” took to the top spot from “I’ll Make Love to You.” Bieber would replicate this feat in 2016 and 2017. First, when “Love Yourself” replaced “Sorry” in February 2016, and again when “Despacito” replaced “I’m the One” in May 2017.
Both Janet Jackson and Cliff Richard are musical legends now, but in 1984 Jackson was just an 18-year-old starting out. They sang the duet “Two to the Power of Love.”
Americans may not know Richard, but Brits sure do. He’s the third-best-selling musical act ever in the UK, only behind the Beatles and Elvis. He peaked in the late ’50s and ’60s.
So, by 1984, he was solidly a musical legend. That year, he teamed up with then up-and-comer Jackson on her second album, “Dream Street,” on the duet “Two to the Power of Love.”
The album didn’t make much of an impact on the charts, but it set her up for global domination when 1986’s “Control” was released.
Enrique Iglesias and Whitney Houston teamed up on the duet “Could I Have This Kiss Forever” in 1999 for his first English-language album.
To help Iglesias break out in America, he enlisted the help of superstar Houston for “Could I Have This Kiss Forever?,” which was also included on her first compilation album, “Whitney: The Greatest Hits.” The duet was released on his album, “Enrique” in 1999, and was officially released as a single in 2000.
Kanye West, Rihanna, and ex-Beatle Paul McCartney all appeared on “FourFiveSeconds” in 2015, sending the internet into a collective tailspin.
Arguably, all three of these artists are musical legends. But there’s something so inherently confusing about Rihanna and West teaming up with McCartney that this must be included.
When “FourFiveSeconds” made it on the Hot 100 at No. 6, it broke a record for longest gap between top-ten singles, as McCartney’s last hit single was 1986’s “Spies Like Us,” which peaked at seven. And when it made it to No. 4, it became McCartney’s first top-five single in 31 years, since his No. 1 song with Michael Jackson, “Say Say Say” in 1983.
Sting and Shaggy released a collaborative album in 2018, called “44/876.” The title refers to the country codes for Sting’s native UK, and Shaggy’s home of Jamaica.
The album won Best Reggae Album at the Grammys in 2019. The album debuted at No. 9 in the UK, making it the first top 1o album for Sting since 2003, and since 2001 for Shaggy.
The rapper best known for “It Wasn’t Me,” and the former front man of the Police might not seem like the most obvious combination, but it works.
Their Tiny Desk Concert has garnered 2.9 million views on YouTube, and has comments like “I like being shocked by seeing something I wouldn’t expect to work. This was a great collaboration,” and “This might be one of my favorite Tiny Desk Concerts.”