Vanilla Ice – 51 – TV Host & Contractor

Robert Matthew Van Winkle a.k.a. Vanilla Ice is a rapper who shot to fame back in the 1990s, owing to his song, Ice Ice Baby. He also did a popular cover version of the song, Play That Funky Music. Ice has released a total of seven studio albums as of today. He is more known these days for hosting his own show titled The Vanilla Ice Project. The program first aired in 2009 and its eighth season just ended in October 2018. That project was such a blessing for him because it has increased his net worth, bringing it to around $10 million.