Now: Janet Jackson
Now in her fifties, Janet Jackson is the mother of her child with Wissam Al Mana. She converted to the Islamic faith, his religion. Unfortunately, they have since gotten a divorce.

Now: Janet Jackson
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Then: Jenny McCarthy
In 1993, Jenny McCarthy entered the entertainment industry as a Playboy model. In the same year, she was declared Playmate of the Year, something that was frowned upon by her Catholic family. She later hosted the MTV dating show called Singled Out alongside Carmen Electra.

Then: Jenny McCarthy