Conchata Ferrell as Berta | Then
Playing as the cynical, sharp-tongued, sassy, hard-working character is Berta, the housekeeper. Though she was probably the only woman in the show that Charlie didn’t develop feelings for, she still offered loads of comic relief for the audience.
Berta takes great satisfaction in making fun of the Harper family for all their unfortunate twists and turns as they amuse her. She is definitely considered a fan favorite!
Denise Richards as Lisa | Then
Played by Denise Richards, Lisa was one of Charlie’s love interests in season 1. She and Charlie had lived together in Charlie’s beach house up until he realized he was not willing to be in a committed relationship.
After the two break up, Lisa discloses to Charlie that she plans to get married. Struck by jealousy and regret, Charlie tries winning her back by pretending he has changed into a family-oriented man. Lisa ends up divorcing her husband for Charlie but is once again dumped because of his fear of commitment.
Denise Richards as Lisa | Now
Denise Richards is definitely a unique addition to this list as she was actually married to Charlie Sheen in real life! The two were married for 4 years, raising their two daughters Lola and Sam.
Though their marriage ended, Richards’ television success certainly did not. After appearing in numerous hit films, Richards starred in the E! reality show, Denise Richards: It’s Complicated. She then became a series regular on the comedy sitcom Blue Mountain State and currently stars in the reality show, The Real Housewives of Beverly Hills.
Conchata Ferrell as Berta | Now
Conchata Ferrell is well known for her character work, receiving two Primetime Emmy Award nominations for her exceptional performances. The American actress has still been active in the industry, even nailing a role as Shirley on the Netflix comedy show, The Ranch.
She was also most recently featured in the film, Deported. But no matter the role given to Ferrell, people will always know and love her for playing Berta!
Jenny McCarthy as Courtney Leopold | Then
Courtney Leopold was the minor recurring character in the show. She was played as the former professional con-artist, and eventually Charlie’s temporary girlfriend. Though Alan warns Charlie of Courtney’s sociopathic tendencies, he still decides to go on with their relationship. Alan is, of course, proven right after Courtney successfully convinces Charlie to give her $50,000 and give her a Ferrari. Talk about lavish needs!
Charlie then proposes to her but ends up not pushing through with the marriage after finding out that her real name is Sylvia and her parents are con-artists in reality. That’s some pretty sketchy stuff right there.