Charlie Sheen Charlie Harper Actor Jon Cryer Alan Harper Actor Angus T. Jones Jake Harper Actor Marin Hinkle Judith Actor Conchata Ferrell Berta Actor Ryan Stiles Dr. Herb Melnick Guest Star Denise Loveday-Kane Mother Guest Star Austin Kane Toddler Guest Star Jenn Liu Gwyneth Guest Star Sacheen Padilla Maureen Guest Star Shantel Wislawski Kim Guest Star Jeanne Simpson Mother 2 Guest Star Shane Roney Toddler 2 Guest Star Chuck Lorre Executive Producer, Writer Lee Aronsohn Executive Producer, Writer Eric Tannenbaum Executive Producer Kim Tannenbaum Executive Producer Mark Burg Executive Producer Oren Koules Executive Producer Mark Roberts Writer Jim Patterson Writer James Widdoes Director