RJDG14

Currently the majority of music being sung by Millennials/Gen-Z has a kind of dribbly sound to the vocals, often with unusual sudden drops at the end of lines. This type of singing didn't really exist before Craig David (c.1999/2000) and became far more common during the latter half of the 2000s. Now most young singers sing this way, and I don't think Autotune is fully responsible, since I've seen buskers who also sing like this.

There were also certain singing styles (though with more variation) common during the 80s and 90s, and singers from this era (Gen-Jones/Gen-X) typically sound different to singers from the 60s and early 70s (Silent/Baby-Boomers).

So would it be true that each generation has a unique singing style (as a generalisation) that most popular music by a certain generation tends to use?

Lisnaholic

Yes, I'm sure singing styles in pop are subject to fashion and change across the decades. The only change I've particularly noticed, though, is this:

In the sixties, a "good" pop singer was expected to deliver the words of the song and keep their breathing to themselves. Even The Beatles, introducing the remarkable-at-the-time non-word, "Yeah" in 1963, were careful to ennunciate it clearly.
But by the eighties I noticed that some artists were no longer hiding the sound of their breathing. For example, Enya with her sultry exhalations and Michael Jackson with his huffing and puffing made a virtue out of sounds that would've been considered unprofessional a generation earlier. They made sexy the kind of sighing and blowing that previously had only turned up on those creepy heavy-breathing stalker moments in horror movies.

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