Alyssa Milano | 49 Years Old

Sometimes, we find help in the places we least expected. For Alyssa Milano, her journey to the entertainment industry probably wouldn’t have happened if it wasn’t for her childhood babysitter. When she was seven years old, her helper brought Milano to an audition for the stage production of Annie and ultimately became one of four out of 1,500 people to land the part. Suffice to say, this was just the beginning of her career.

Since then, Milano has made numerous investments in the entertainment industry, both as an actress and producer. With that said, she’s now often regarded for her work on projects such as Melrose Place, My Name Is Earl, and Who’s the Boss? Besides appearing on screen or working behind the scenes, Milano released a children’s book titled Hope: Project Middle School, and another book compiling thirty-two essays titled Sorry Not Sorry.