This is a mix of my humble opinion and the result of some research:
During the 80s decade the boundaries between pop, R&B, rock and rap started to be less strict, for example:
A R&B and disco singer as Michael Jackson was considered at the first 80s, included a pop-rock song called Beat It (with the help of an Eddie Van Halen riff) in the same album as Billie Jean and Wanna Be starting Something.
Jump by Van Halen. A hard rock song where the main riff is not played in a guitar but in a synthethizer.
Walk This Way. Flawless merge of a Aerosmith's song in a rap by RUN DMC.
Def Leppard's Hysteria album. Hard rock for all the audiences.
Music producers discovered that those songs appealed to wider audiences, because they blended together different styles. It's very good for the business if rap fans and Aerosmith fans buy the same single.
So, during the 80s the styles-mix started to appear in songs like I Feel For You, a Prince-written song sung by Chaka Khan with the collaboration of Stevie Wonder and the rapper Melle Mel or the song Don't Rock The Boat of Midnight Star with a rap section by Ecstasy, a rapper from the group Whodini. However the first one is credited to Chaka Kan and the later to Midnight Star. The collaborators were simply ignored.
The breakthrough came in july 1990 in a song called She Ain’t Worth It by Glenn Medeiros featuring Bobby Brown. It is the first song with the word featuring that went to be a No. 1 hit.
Medeiros was at the time a pop singer that had achieved a top 20 in 1987 with the song Nothing's Gonna Change My Love For You, and Bobby Brown was a mega-star well stablished in the New Jack Swing genre.
Brown rapped in the Medeiros song during a few seconds at the beginning and in the middle, it was enough to demonstrate the commercial force of mxing a rap bridge inside a pop song.
It helped to make rap a more mainstream genre and from then the collaborations started to go in both ways, pop songs with rap collaborations, like:
- Jam - Michael Jackson featuring Heavy D
- Got til It’s Gone - Janet Jackson featuring Q-Tip
- Crazy In Love - Beyoncé featuring Jay-Z
or the other way, rappers receiving pop collaborations:
- Whatta Man - Salt-n-Pepa featuring En Vogue
- Dilemma - Nelly featuring Kelly Rowland
In the decade of the 2010's The EDM (Electronic Dance Music) scene used the same strategy to go from sub-genre with no known faces to mainstream. Yes, I'm talking about David Guetta or Skrillex. They have received a lot of collaborations that helped them to go from DJing in Ibiza discos to the top of the charts. We can include Daft Punk under the same way of work.
Or, the big example of all examples, Uptown Funk by Mark Ronson featuring Bruno Mars where the contribution of Mark Ronson seems to be more as a producer / arranger.
In general, the featuring thing is nothing but a way to reach to more audience and lastly to sell more singles.
If you consider yourself a Rihanna fan, you are getting also into Calvin Harris, Eminem, Jay-Z, T.I., Drake,etc. and in the long run you'll be interested in some of them.
Credit where is due: The main source of this explanation is this article.