27. Little Jimmy Osmond
Role: Himself Show: The Andy Williams Show (1962) Net Worth: Estimated at $8 million*
Little Jimmy Osmond gained fame as a member of his family’s band, featured on The Andy Williams Show. Enjoying a successful solo career, Osmond garnered six gold records, a gold album, and a platinum album independently of his Osmond family ties.

Now retired, Osmond faced health challenges in 2018, experiencing a stroke after his performance as Captain Hook in Peter Pan. Subsequently, he declared a “long overdue” hiatus from show business in spring 2019, likely extending indefinitely.