19 Episodes 2007 - 2008
Charlie Harper (Charlie Sheen) and the gang are up to their old tricks in the CBS comedy's fifth season, which was shortened to 19 episodes due to the 2007-08 Writers Guild strike. Highlights include Alan (Jon Cryer) and Charlie doing their best to get Jake (Angus T. Jones) ready for his first day of junior high; Alan's date (Janeane Garofalo) behaving strangely after they have sex; Charlie letting Alan arrange a date for him with a woman (Ming-Na Wen) his own age, but being pleasantly surprised when he babysits her 4-year-old son; Alan and Charlie having an argument that's so upsetting that Alan actually moves out and takes Jake to live with Evelyn (Emmy nominee Holland Taylor), who is preparing to get married for the fifth time; and Charlie considering a new career as a singer of children's songs. Guest stars include Robert Wagner, Jenny McCarthy and Jane Lynch.
Large Birds, Spiders and Mom
Mon, Sep 24, 2007 30 mins
Alan and Charlie do their best to get Jake ready for his first day of high school, but they end up doing more harm than good.
Media Room Slash Dungeon
Mon, Oct 1, 2007 30 mins
Alan's date behaves strangely after they have sex; and Charlie acts weird following a meeting with his mother.
Dum Diddy Dum Diddy Doo
Mon, Oct 8, 2007 30 mins
Having grown tired of young vacuous women, Charlie lets Alan arrange a date for him with a woman his own age.
City of Great Racks
Mon, Oct 15, 2007 30 mins
Charlie is ready to consummate his relationship with Linda, but he keeps seeing the face of Rose everywhere he goes.
Putting Swim Fins on a Cat
Mon, Oct 22, 2007 30 mins
Charlie babysits Linda's 4-year-old son, and he must find ways to keep the boy entertained.
Help Daddy Find His Toenail
Mon, Oct 29, 2007 30 mins
Jake sneaks out to a concert that Alan told him he couldn't attend. Meanwhile, Charlie's girlfriend is embarrassed to be seen in public with him.
The Leather Gear Is in the Guest Room
Mon, Nov 5, 2007 30 mins
An argument with Charlie prompts Alan to take Jake and move in with Evelyn.
Is There a Mrs. Waffles?
Mon, Nov 12, 2007 30 mins
Charlie may have a new career as a children's singing star.
Mon, Nov 19, 2007 30 mins
Charlie fights his attraction to his soon-to-be stepsister (Jenny McCarthy). Teddy: Robert Wagner.
Kinda Like Necrophilia
Mon, Nov 26, 2007 30 mins
Alan learns that it was Charlie who stole his high-school girlfriend years ago, and now he wants to get revenge. Gabrielle: Justine Eyre. Charity: Laura McLauchlin.
Meander to Your Dander
Mon, Mar 17, 2008 30 mins
Charlie teaches Alan how to break up with a woman. Donna: Kimberly Quinn. Brenda: Eve Gordon. Georgia: Sandra Dee Robinson. Lilly: Gracie Maddox.
A Little Clammy and None Too Fresh
Mon, Mar 24, 2008 30 mins
Rose returns from England and nurses a sick Charlie in her own unique way. Lulu: Cerina Vincent. Rose: Melanie Lynskey.
The Soil Is Moist
Mon, Mar 31, 2008 30 mins
Alan dates a friend of Judith's, and the woman gossips about Judith's sex life. Herb: Ryan Stiles. Cynthia: Jessica Tuck.
Mon, Apr 14, 2008 30 mins
Charlie and Jake go on a double date; and Charlie arranges a date with a prostitute for Alan.
Rough Night in Hump Junction
Mon, Apr 21, 2008 30 mins
Alan is afraid that Charlie's womanizing has reached a dangerous level. Mia: Emmanuelle Vaugier. Dr. Freeman: Jane Lynch. Pepper: Anastasia Roark. Gretchen: Andrea Bogart. Sam: Barry Livingston. Fred: Clint Carmichael.
Look at Me, Mommy, I'm Pretty
Mon, Apr 28, 2008 30 mins
While Alan plans Evelyn's wedding, Charlie plans his next conquest---his future stepsister.
Fish in a Drawer
Mon, May 5, 2008 30 mins
George Eads has a cameo in this episode in which a CSI team investigates a death at Charlie's house.
If My Hole Could Talk
Mon, May 12, 2008 30 mins
Charlie falls for an older woman who writes self-help books; and Alan and Jake fight about a school assignment.
Waiting for the Right Snapper
Mon, May 19, 2008 30 mins
In the fifth-season finale, Charlie is tempted when he meets the daughter of the older woman he is dating.