Ray Romano

Ray Romano performed his first late-night comedy set on The Late Show with David Letterman, and from there a show was developed with him as the star. The series, Everybody Loves Raymond, became one of the most successful family sitcoms ever.

After nine successful seasons, treating each episode as a final project of the week, the show ended in 2005. His residuals are a substantial $18 million per year, according to Forbes.