Take a Look at the Cast of Two and a Half Men Today

Herb Melnick, Judith’s second husband, was played by Ryan Stiles. As Jake’s stepfather, Herb was well-meaning but goofy, often the butt of Charlie and Alan’s jokes. His awkwardness and desire to fit in made him a sympathetic character, while his marriage to Judith added plenty of comedy to Alan’s already complicated life.

By the time he joined Two and a Half Men, Stiles was already a comedy star, best known for Whose Line Is It Anyway? and The Drew Carey Show. His improvisational background gave Herb an extra charm, and fans loved his mix of clumsiness and sincerity.