Kathie Lee, Age 66, Today – $5 Million

Popular for co-hosting Live with Regis and Kathie Lee (1985-2000) and NBC‘s Today show (2008-2019), Kathie Lee Gifford is also a singer, songwriter, and author. She won her first Daytime Emmy award in 2010 and generates an annual income of $5 million, while her net worth sits at $60 million. 

Gifford left the Today show to follow a career in acting and producing movies. She hopes to focus on creating movies about losing a loved one and about being a widow since she recently underwent the experience firsthand after losing her husband in 2015.