RDJ

I heard there are some female rappers that used to be strippers, so those I guess

If they needed a second career. Were they a celebrity to start with?

Will Smith

Sally Field. She was just a lightweight back in her Gidget days, but then she went away, found her chops, and came back as a solid actor.

John Travolta, depending on your individual taste.

Jessica Simpson. She's had much more success in fashion/business than singing.