Unlikely Song Duets

Some of the biggest songs in pop chart history feature collaborations between artists. You probably know songs by Mariah Carey and Boyz II Men, Paul McCartney and Michael Jackson, and Beyonce and Jay-Z. All of these artists are superstars.* But what about songs where one artist is a star (or becomes one) and the other isn't quite on that level? That is the point of this post.

Before I share videos, there are a few rules. Both artists need to be listed in the credits. One of the obvious songs for this post would be “Somebody’s Watching Me” by Rockwell. Although Michael Jackson sings the chorus, the song is credited only to Rockwell. Same with "Opposites Attract" by Paula Abdul. MC Skat Cat is wrongfully not listed.

I'm also only including songs that made an impact on the charts. Deep album cuts like a song by Taylor Swift featuring a random family member don't make a list. (I'm not aware of any song, but if there's a Taylor Swift-D'Andre Swift collaboration, it didn't make the cut.

Rihanna featuring Mikky Ekko - Stay

Rihanna performed at last year’s Super Bowl, has sold about 250 million albums worldwide, and has over 30 top 10 hits. Mega star! While Mikky Ekko is a very successful music writer, his singing career is probably best (and maybe only) known for Stay.

Coolio featuring L.V. - Gangsta's Paradise

The late Coolio won a Grammy for this song and sold nearly 5 million albums in the US. Plus, he performed the opening sequence to Kenan & Kel and has multiple television and film credits. Meanwhile, L.V. released five albums with one peaking at #59 on the R&B album chart, another reaching #100, and the remaining three not charting at all. 

Elton John, Kiki Dee - Don't Go Breaking My Heart

I learned that Kiki Dee released 22 albums. 22!! While she's had plenty of success in the U.K. and reached #12 in the American chart with the 1974 song I've Got the Music in Me, it's not fair to compare her success with the resume of Sir Elton John.

Lady Gaga featuring Colby O'Donis - Just Dance

Just Dance is Lady Gaga's first song and with Colby O'Donis having some success with his own first single with Akon just prior to this song, perhaps she or someone at the studio thought a different voice would give the song a little extra attention. Two relatively new artists coming together. Of course, Lady Gaga followed this up with Poker Face and never looked back on her way to mega-stardom with Grammys, an Oscar, and a Super Bowl halftime show. Meanwhile, Colby O'Donis may or may not have hooked up with Hulk Hogan's daughter on the Hogan family reality show. I should also mention that Just Dance gave me the idea for this post. 

Shaggy featuring RikRok - It Wasn't Me

This was a smash hit. Shaggy has two Billboard Music Awards and two Grammys, one for It Wasn't Me and another for his collaboration with Sting. He appeared on The Masked Singer in 2022 and toured with TLC, En Vogue, and Sean Kingston last year. Ricardo "RikRok" Ducent doesn't appear to have a Wikipedia page.

Sting featuring Cheb Mami - Desert Rose

Since I mentioned Sting, you may be familiar with his musical career. He also has an acting career including appearing in several episodes of Only Murders in the Building which I just started watching. When not being accused of murder on the show, he's done pretty well for himself. Born in Algeria, Cheb Mami released over a dozen albums between 1985 and 2006, though none appear to have significant sales in the United States. Is it fair to include someone with international success but not success in the US on this list? Maybe. For example, No Doubt won Grammys with Jamaican DJ/singers Bounty Killer on Hey Baby and Lady Saw on Underneath It All respectively. I should also mention that Cheb's music career seems to have ended after the 2006 album. He went to jail for doing some bad things in 2011 and later had to pay an artist for plagiarism.

Glenn Medeiros featuring Bobby Brown - She Ain't Worth It

The Hawaiian singer had a #12 song with 1987's Nothing's Gonna Change My Love For You and his collaboration with Bobby Brown went to #1. Medeiros had five other singles reach the lower ranks of the charts between 1987-1990, the highest charting song being All I'm Missing Is You featuring Ray Parker Jr. (hold that thought) at #32 and released several albums. Then, he turned to education becoming a teacher, principal, and professor and earning a doctorate. I'm sure at least one student told him that she ain't worth it during a meeting in the principal's office! After New Edition, Brown embarked on a successful solo career with 8 top 10 hits including On Our Own from Ghostbusters II in case you were waiting for that Ray Parker Jr. connection. Of course, Brown also received enormous attention with his sometimes turbulent marriage to Whitney Houston. And this gives me the perfect opportunity to share this video of Brown meeting The Dalai Lama and getting introduced as Whitney's husband.

Olly Murs featuring Flo Rida - Troublemaker

This is another case of someone being successful internationally but not domestically. Olly Murs was on the UK version of The X Factor and has a string of hits there as well as numerous television appearances including as a judge on The Voice UK. His success hasn't transltaed to the United States where Troublemaker is his only top 40 song. Meanwhile, Flo Rida has so many songs over the last 15 years featured in films and commercials. You probably know a lot more of his songs than you think. 

A few others for your consideration:

Santana featuring Alex Band (from the band The Calling) - Why Don't You & I

Drake featuring Majid Jordan - Hold On, We're Going Home

I'm sure that I've missed others. Please feel free to add your suggestions in the comments section.

* While you probably wouldn't include Boyz II Men in this group, they won 4 Grammys and have 9 top 3 hits. Not too shabby!