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PRIMETIME EMMYS® 2X nominee in 2013

Two and a Half Men

The Emmy-winning laughfest continues as television's leading comedy. With Jake (Angus T. Jones) now entering junior high school, his dad, Alan (Jon Cryer), reliving his high school dating history and Charlie (Charlie Sheen) finally maturing a little himself, will there be room for three men in Charlie's Malibu beach pad? You won't want to miss a single episode from this hilarious season!
IMDb 7.1200319 episodes
TV-14
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Episodes

  1. S5 E1 - Large Birds, Spiders and Mom
    September 23, 2007
    21min
    TV-14
    In the fifth season premiere, Charlie and Alan try to prepare Jake for his first day of junior high school -- but they might end up traumatizing him instead.
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  2. S5 E2 - Media Room Slash Dungeon
    September 30, 2007
    22min
    TV-14
    Charlie reacts oddly after an evening with his mother. And Alan's date, Sharon (JANEANE GAROFALO - "The Larry Sanders Show," "The West Wing"), reacts oddly after having sex with Alan.
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  3. S5 E3 - Dum Diddy Dum Diddy Doo
    October 7, 2007
    22min
    TV-14
    Tired of dating vapid young women, Charlie allows Alan to introduce him to a sophisticated, intelligent municipal court judge, Linda.
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  4. S5 E4 - City of Great Racks
    October 14, 2007
    22min
    TV-14
    In the landmark 100th episode, Charlie gets closer to consummating his relationship with Linda, but he keeps seeing Rose's face everywhere he turns. Recurring guest star JANE LYNCH appears as Dr. Freeman.
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  5. S5 E5 - Putting Swim Fins on a Cat
    October 21, 2007
    22min
    TV-14
    Charlie has to find creative ways to entertain the 4-year-old son of his girlfriend, Linda (recurring guest star MING WEN). Meanwhile, Alan becomes a human "guinea pig."
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  6. S5 E6 - Help Daddy Find His Toenail
    October 28, 2007
    21min
    TV-14
    Charlie's girlfriend, Linda (recurring guest star MING WEN), is embarrassed to be seen in public with him. Meanwhile, despite Alan forbidding it, Jake sneaks out to a concert.
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  7. S5 E7 - Our Leather Gear is in the Guest Room
    November 4, 2007
    21min
    TV-14
    Charlie and Alan argue over Alan's place in the house, prompting Alan and Jake to move in with Evelyn. Recurring guest star ROBERT WAGNER appears as Teddy, Evelyn's boyfriend.
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  8. S5 E8 - Is There a Mrs. Waffles?
    November 11, 2007
    20min
    TV-14
    Charlie finds success as a children's singing star, making Alan miserable. Guest star RICHARD KIND ("Spin City") appears as Artie, an executive at Charlie's record label.
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  9. S5 E9 - Tight's Good
    November 18, 2007
    21min
    TV-14
    After Evelyn and Teddy become engaged, Charlie struggles to fight his attraction to Teddy's daughter, Courtney, Charlie's soon-to-be stepsister.
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  10. S5 E10 - Kinda Like Necrophilia
    November 25, 2007
    22min
    TV-14
    While trying to help Jake get over a breakup, Alan discovers that it was Charlie who stole his high school girlfriend. Alan seeks revenge on Charlie by following the same advice Charlie dispenses to Jake.
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  11. S5 E11 - Meander to Your Dander
    March 16, 2008
    22min
    TV-14
    Seeing Alan not fully passionate about his relationship, Charlie coaches Alan in the fine art of breaking up with a woman.
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  12. S5 E12 - A Little Clammy and None Too Fresh
    March 23, 2008
    22min
    TV-14
    Rose (recurring guest star MELANIE LYNSKEY), Charlie's lovable stalker, is back from England and takes strange care of a very sick Charlie.
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  13. S5 E13 - The Soil is Moist
    March 30, 2008
    20min
    TV-14
    Alan dates one of his ex-wife's friends who reveals a secret about Judith's sex life. Recurring guest star RYAN STILES appears as Judith's second husband.
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  14. S5 E14 - Winky-Dink Time
    April 13, 2008
    22min
    TV-14
    Charlie goes with Jake on a double date and sets Alan up with a prostitute. Recurring guest star MELANIE LYNSKEY appears as Rose.
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  15. S5 E15 - Rough Night in Hump Junction
    April 20, 2008
    22min
    TV-14
    Alan worries that Charlie's womanizing is out of control. JANE LYNCH returns as Charlie's therapist, and EMMANUELLE VAUGIER returns as Charlie's former fiancee, Mia.
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  16. S5 E16 - Look at Me, Mommy, I'm Pretty
    April 27, 2008
    22min
    TV-14
    Alan plans Evelyn's wedding to Teddy (ROBERT WAGNER), while Charlie pursues his future stepsister and Teddy's devious daughter, Courtney (JENNY McCARTHY).
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  17. S5 E17 - Fish in a Drawer
    May 4, 2008
    22min
    TV-14
    A CSI team investigates a mysterious death at Charlie's house. George Eads ("CSI: Crime Scene Investigation") makes a cameo appearance.
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  18. S5 E18 - If My Hole Could Talk
    May 11, 2008
    22min
    TV-14
    Charlie finds himself attracted to Angie (recurring guest star SUSAN BLAKELY), an older woman who writes self-help books. Meanwhile, Alan and Jake battle over a school assignment.
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  19. S5 E19 - Waiting for the Right Snapper
    May 18, 2008
    22min
    TV-14
    Charlie tries to resist temptation when he meets the grown daughter of the woman he's dating (SUSAN BLAKELY) and realizes they've met before. JANE LYNCH guest stars as Dr. Freeman.
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Details

More info

Content advisory
Violencesubstance usealcohol usefoul languagesexual content
Subtitles
None available
Directors
James WiddoesGary HalvorsonPamela FrymanJeff MelmanRob SchillerAndy AckermanTed WassAndrew D. WeymanLee AronsohnJon Cryer
Starring
Charlie SheenJon CryerAngus T. Jones
Studio
WB
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