• Air date: 24 Sep '07 19 episodes
      The fifth season of Two and a Half Men originally aired on CBS from September 24, 2007, to May 19, 2008. A total of only 19 episodes were aired due to the 2007–2008 Writers Guild of America strike. Unlike the previous seasons, the Season 5 DVD came without a gag reel. This was the shortest season in the history of the show until the eighth season ended after 16 episodes due to the firing of Charlie Sheen.
  • List of Episodes (19)
    • 1. Large Birds, Spiders and Mom

      24 Sep '07
      Jake is getting ready to start a new school as he graduates to Junior High. Alan and Charlie take him school shopping and find themselves in trouble.
    • 2. Media Room Slash Dungeon

      01 Oct '07
      Charlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.
    • 3. Dum Diddy Dum Diddy Doo

      08 Oct '07
      Alan convinces Charlie that he needs to date more respectable women and sets him up with a judge. The two double date and their waitress happens to be one of Alan's ex-girlfriends. Charlie's date backfires the following morning, when he ends up in court in front of the judge.
    • 4. City of Great Racks

      14 Oct '07
      Charlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns.
    • 5. Putting Swim Fins on a Cat

      23 Oct '07
      Charlie has to come up with ways to keep his girlfriend's 4-year-old amused; Alan becomes a test subject.
    • 6. Help Daddy Find His Toenail

      30 Oct '07
      Charlie's girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.
    • 7. The Leather Gear is in the Guest Room

      05 Nov '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.
    • 8. Is There a Mrs. Waffles?

      12 Nov '07
      Charlie writes a children’s song and finds success as Charlie Waffles. The children love him and the mothers seem to as well. Charlie's new found fame irritates Alan.
    • 9. Shoes, Hats, Pickle, Jar Lids.

      19 Nov '07
      Charlie fights his attraction for Teddy's daughter.
    • 10. Kinda Like Necrophilia

      26 Nov '07
      Alan finds out that Charlie stole his girlfriend and works on a plan to get back at Charlie, even though this happened when they were in high school.
    • 11. Meander to Your Dander

      17 Mar '08
      When Alan finds himself wanting to break up with a woman, Charlie offers his expertise.
    • 12. A Little Clammy and None Too Fresh

      24 Mar '08
      Rose returns from England, and plays nurse rather oddly for an ill Charlie.
    • 13. The Soil is Moist

      31 Mar '08
      Alan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.
    • 14. Winky-Dink Time

      14 Apr '08
      Charlie double-dates with Jake and fixes Alan up with a hooker.
    • 15. Rough Night in Hump Junction (aka His Ugly Bundle)

      21 Apr '08
      Alan feels Charlie is unable to control his womanizing ways.
    • 16. Look At Me, Mommy, I'm Pretty

      28 Apr '08
      Alan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister.
    • 17. Fish in a Drawer

      05 May '08
      CSIs investigate a death at Charlie's house.
    • 18. If My Hole Could Talk

      12 May '08
      Charlie's attracted to an older self-help author. Alan and Jake clash over a project for school.
    • 19. Waiting for the Right Snapper

      19 May '08
      When Charlie meets Angie's soon to be daughter-in-law, he realizes it's not for the first time.