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The fifth season of Two and a Half Men began airing on September 24, 2007 and ended on May 19, 2008 with 19 episodes. It was released on DVD on May 12, 2009.
Cast[]
Main[]
- Charlie Sheen as Charlie Harper (19 episodes)
- Jon Cryer as Alan Harper (19 episodes)
- Angus T. Jones as Jake Harper (19 episodes)
- Marin Hinkle as Judith Harper-Melnick (4 episodes)
- Conchata Ferrell as Berta (17 episodes)
- and Holland Taylor as Evelyn Harper (9 episodes)
Recurring[]
- Melanie Lynskey as Rose (5 episodes)
- Ming-Na Wen as Linda Harris (4 episodes)
- Robert Wagner as Teddy Leopold (4 episodes)
- Jane Lynch as Dr. Linda Freeman (3 episodes)
- Kimberly Quinn as Donna (2 episodes)
Guest-Star[]
- Jenny McCarthy as Courtney Leopold (3 episodes)
- Ryan Stiles as Herb Melnick
Episodes[]
| Image | Title | Air Date | # | Summary | Title quotation from |
|---|---|---|---|---|---|
|
Large Birds, Spiders and Mom | September 24, 2007 | 5.01 | Jake is getting ready to start a new school as he advances to junior high, but his dad and uncle's scary stories might end his academic career a bit early. | Alan |
|
Media Room Slash Dungeon | October 1, 2007 | 5.02 | Charlie acts strangely after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning. | Evelyn |
|
Dum Diddy Dum Diddy Doo | October 8, 2007 | 5.03 | Having grown tired of young vacuous women, Charlie lets Alan arrange a date for him with a woman (Ming-Na Wen) his own age. | Charlie |
|
City of Great Racks | October 15, 2007 | 5.04 | Charlie is getting serious with Linda. But lately he seems to be seeing his ex-stalker, Rose. Has she returned from England, or is it his imagination? | Jake |
|
Putting Swim Fins on a Cat | October 22, 2007 | 5.05 | Charlie has to come up with ways to keep his girlfriend's four-year-old son amused. Meanwhile, Alan becomes a test subject. | Alan |
|
Help Daddy Find His Toenail | October 29, 2007 | 5.06 | A medication mix-up causes Charlie to humiliate Linda at an important dinner, and Jake disobeys his dad's orders and sneaks out to attend a rock concert. | Alan |
|
The Leather Gear Is in the Guest Room | November 5, 2007 | 5.07 | After Alan and Charlie have a fight about Alan's role in the house, Alan packs Jake up and moves in with his mother. | Evelyn |
|
Is There a Mrs. Waffles? | November 12, 2007 | 5.08 | Charlie writes children's songs and finds success as Charlie Waffles. The kids and their parents love him, even signing CDs of his jingles. | One of Charlie's single-mom fans |
|
Shoes, Hats, Pickle Jar Lids | November 19, 2007 | 5.09 | Charlie ignores his future step-father's advice and gets involved with his daughter, and he learns the hard way that he should have heeded the warning. | Courtney |
|
Kinda Like Necrophilia | November 26, 2007 | 5.10 | Alan finds out that Charlie stole his girlfriend in high school, so he sets out to even the score. | Charlie |
|
Meander to Your Dander | March 17, 2008 | 5.11 | Alan's latest relationship has grown stale, so he turns to Charlie for advice about how to break up with her. | Alan |
|
A Little Clammy and None Too Fresh | March 24, 2008 | 5.12 | Rose returns from England and plays nurse for an ill Charlie. Alan feels Jake pulling away from him. | Charlie |
|
The Soil is Moist | March 31, 2008 | 5.13 | Alan dates a friend of Judith's, and the woman gossips about Judith's sex life. | Herb |
|
Winky-Dink Time | April 14, 2008 | 5.14 | Charlie sets up Alan with a prostitute, and accompanies Jake on a double date. | Alan |
|
Rough Night in Hump Junction | April 21, 2008 | 5.15 | Alan feels Charlie is unable to control his womanizing ways. | Berta |
|
Look at Me, Mommy, I'm Pretty | April 28, 2008 | 5.16 | Charlie figures out how to get more acquainted with his future step-sister, Courtney. | Evelyn |
|
Fish in a Drawer | May 5, 2008 | 5.17 | Parody of "CSI" in which Teddy's death body is found in Charlie's bed, and detectives try to figure out who is the killer. | Evelyn |
|
If My Hole Could Talk | May 12, 2008 | 5.18 | Charlie's attracted to an older self-help author. Meanwhile, Alan tries his son to read a book but Jake loses continuously. | Charlie |
|
Waiting for the Right Snapper | May 19, 2008 | 5.19 | When Charlie meets the fiancée of Angie's grown-up son, he realizes it's not for the first time. Alan tries to get Jake to study for his algebra final. | Charlie |
