What are some examples in which a singer with a distinct singing style decided to change things up?

Mick Jagger sang country and western

Shena Easton
Whitney Houston
Miriah Carry
and others started out singing like normal people then started trying to hit every note on the scale in every measure.

(Sorry about the spelling.)

Although I generally like the album Some Girls, watching that video is kind of painful lol

I guess you’d have to say Ozzy Osbourne.

The original name of Black Sabbath was The Polka Tulk Blues Band.

Mozart once wrote this

Rod Stewart used to sing blues and rock and then drifted into disco and pop.

I once heard Roger Daltry sing Irish ballads with the Chieftains.

Bob Dylan before and after the motorcycle accident. (not his choice to get in the wreck)