Critics and audiences often highlight several episodes that defined the season’s "respectable, steady baseline" of humor:

: Makes a memorable guest appearance as Charlie’s loud new neighbor.

: A relatable exploration of Charlie hitting his 40s and struggling to keep up with a much younger girlfriend. Guest Stars & Ensemble Highlights

: Widely considered the season's (and perhaps series') best episode, this Christmas special subverts holiday sentimentality with a chaotic party and a near-miss encounter with a woman who might be Charlie's sister.

: Explores Charlie’s psychological hang-ups by having him date Lydia, a woman who is a literal "carbon copy" of his mother, Evelyn.

: A central narrative thread involves Alan’s desperate attempt to get Judith to remarry Herb Melnik (Ryan Stiles) so he can finally stop paying alimony.