Macaulay Culkin Now
Mr. Culkin, while he doesn’t appear to be in his 40s, has had a difficult time with time. He took a break from acting in the mid-to-late 1990s but returned later and has since played several films. He was also the lead singer for the New York-based pizza-themed band The Pizza Underground. (That Home Alone remake, Macaulay, is still in the works.)
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Lil’ Kim Then
In the 1990s, Lil’ Kim was known as the Queen Bee of the rap game. Her debut album, Hard Core, was certified double platinum in 1996, making her one of only three female rappers with three or more platinum-certified studio albums (the others being Missy Elliot and Nicki Minaj).