[s3e23] That's Midlife -

, Benjamin Salisbury , and Madeline Zima as the Sheffield children. Guest Stars :

Feeling like his life has been a failure, Maxwell undergoes several stereotypical changes: [S3E23] That's Midlife

Concerned for his well-being, Fran tricks him into seeing a psychologist. In a memorable guest appearance, (playing a substitute psychologist) officially diagnoses him with a mid-life crisis. Fran ultimately must convince Maxwell that his life has been a success before his crisis leads to further professional disaster. Cast and Key Guest Stars Main Cast : Fran Drescher as Fran Fine. Charles Shaughnessy as Maxwell Sheffield. Daniel Davis as Niles. Lauren Lane as C.C. Babcock. , Benjamin Salisbury , and Madeline Zima as

: He trades his signature suits and ties for jeans, T-shirts, and leather jackets. Hair : He dyes his distinctive gray streak to look younger. Fran ultimately must convince Maxwell that his life

: This episode is often cited by fans and fashion guides for its winter outfits , particularly a specific look Fran wears during the episode.

: Plays the substitute psychologist who diagnoses Maxwell.