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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Episode
Original Air Date
Synopsis
 
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1. Large Birds, Spiders and Mom [HD]
September 24, 2007
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. Media Room Slash Dungeon [HD]
October 1, 2007
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. Dum Diddy Dum Diddy Doo [HD]
October 8, 2007
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. City of Great Racks [HD]
October 15, 2007
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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$2.99
5. Putting Swim Fins on a Cat [HD]
October 22, 2007
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. Help Daddy Find His Toenail [HD]
October 29, 2007
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. Our Leather Gear is in the Guest Room [HD]
November 5, 2007
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. Is There a Mrs. Waffles? [HD]
November 12, 2007
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. Tight's Good [HD]
November 19, 2007
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. Kinda Like Necrophilia [HD]
November 26, 2007
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. Meander to Your Dander [HD]
March 17, 2008
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. A Little Clammy and None Too Fresh [HD]
March 24, 2008
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. The Soil is Moist [HD]
March 31, 2008
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. Winky-Dink Time [HD]
April 14, 2008
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. Rough Night in Hump Junction [HD]
April 21, 2008
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 fiance?e, Mia.
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16. Look at Me, Mommy, I'm Pretty [HD]
April 28, 2008
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. Fish in a Drawer [HD]
May 5, 2008
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. If My Hole Could Talk [HD]
May 12, 2008
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. Waiting for the Right Snapper [HD]
May 19, 2008
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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Synopsis: 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.
Synopsis: Charlie Sheen and Jon Cryer star in this Emmy-nominated comedy. Sheen plays a Malibu bachelor with an easy way with women. His casual lifestyle is interrupted when his uptight brother (Cryer) and his son stay with him. Despite the complexities of their lives, this unusual family unit promises to make each one of them a better man.
Season year: 2008
Network: CBS
ASIN: B002MOUC0U
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