Since “The Bert Show” morning radio show launched in 2001, there has been one constant: Bert Weiss, the man who created it. Weiss has seen cast members come and go, some smoothly, some not so much.

After 25 years on air, Bert Weiss will retire from The Bert Show this October, ending the Westwood One-syndicated morning program. Weiss launched the show in Atlanta in 2001, expanding into more than ...