From:
To:
He
literally turned into a tap dancing c00n:
Will.I.Am been literally tappin' for so long now, I completely forgot. He shoulda been in the poll. It's turned out to be a very lucrative reinvention.
Can't believe nobody mentioned Everlast
Started like this
To this
Then this
Very radical. When he dropped Whitey Ford, I was like

... going back to your roots as they all do, eh.
but it doesn't appear lucrative enough to make top tier even tho he went triple plat eventually off Whitey Ford. He even named it Whitey Ford (is Everlast a baseball historian?)

... and then followed the shyt up with White trash or some shyt
How about Young Buck? He was a nobody when he was 1 of Juvenile's UTP artists until he got with G-Unit.
You can sorta say the same thing with Meek Mill. He was just another up & coming artist when he was 1 of T.I.'s Grand Hustle artists. He didn't become relevant until he got with Rick Ross & his Maybach Music imprint.
Natural progression.
Cam'ron.
He reinvented EVERYTHING about himself. Style, flow, everything
As another poster pointed out, Cee-Lo should be up there too. Homie went from rappin about Behold the Pale Horse concepts to dressing up like a flamingo with a parrot on his shoulder... and he caked off of his reinvention heavy.
But yeah, Reinvent yourself, brethren.
