George Michael tried to move away from teen pop to R&B, with some success.
Peter Gabriel left Genesis to create very different music.
Alanis Morrisette is probably one of the biggest transormations - she started out as a Debby Gibson-esque teeny bopper as “Alanis”, and then about four years after that phase appeared out of nowhere with ‘Jagged Little Pill’.
Billy Joel has had some critical success with his attempt to move into classical music. Paul McCartney, on the other hand, tried it and failed miserably.
Ringo Starr made a successful country album called “Beaucoups of Blues”.
Waylon Jennings started out as a Rock N’ Roller, playing with Buddy Holly among others. Then he went to Nashville and became a country ‘Outlaw’.
Garth Brooks/Chris Gaines - Perhaps the ultimate suicide.