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Two and a Half Men

Episodes

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.

Episode 1

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.

Where to Watch
Two and a Half Men, Season 5 Episode 1 image

Episode 2

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.

Where to Watch
Two and a Half Men, Season 5 Episode 2 image

Episode 3

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.

Where to Watch
Two and a Half Men, Season 5 Episode 3 image

Episode 4

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.

Where to Watch
Two and a Half Men, Season 5 Episode 4 image

Episode 5

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.

Where to Watch
Two and a Half Men, Season 5 Episode 5 image

Episode 6

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.

Where to Watch
Two and a Half Men, Season 5 Episode 6 image

Episode 7

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.

Where to Watch
Two and a Half Men, Season 5 Episode 7 image

Episode 8

Is There a Mrs. Waffles?

Mon, Nov 12, 2007 30 mins

Charlie may have a new career as a children's singing star.

Where to Watch
Two and a Half Men, Season 5 Episode 8 image

Episode 9

Tight's Good

Mon, Nov 19, 2007 30 mins

Charlie fights his attraction to his soon-to-be stepsister.

Where to Watch
Two and a Half Men, Season 5 Episode 9 image

Episode 10

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.

Where to Watch
Two and a Half Men, Season 5 Episode 10 image

Episode 11

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.

Where to Watch
Two and a Half Men, Season 5 Episode 11 image

Episode 12

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.

Where to Watch
Two and a Half Men, Season 5 Episode 12 image

Episode 13

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.

Where to Watch
Two and a Half Men, Season 5 Episode 13 image

Episode 14

Winky-Dink Time

Mon, Apr 14, 2008 30 mins

Charlie and Jake go on a double date; and Charlie arranges a date with a prostitute for Alan.

Where to Watch
Two and a Half Men, Season 5 Episode 14 image

Episode 15

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.

Where to Watch

Episode 16

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.

Where to Watch
Two and a Half Men, Season 5 Episode 16 image

Episode 17

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.

Where to Watch
Two and a Half Men, Season 5 Episode 17 image

Episode 18

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.

Where to Watch
Two and a Half Men, Season 5 Episode 18 image

Episode 19

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.

Where to Watch
Two and a Half Men, Season 5 Episode 19 image