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The Best Episodes of Two and a Half Men Season 5

Every episode of Two and a Half Men Season 5 ranked from best to worst. Discover the Best Episodes of Two and a Half Men Season 5!

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A hedonistic jingle writer's free-wheeling life comes to an abrupt halt when his brother and 10-year-old nephew move into his beach-front house.

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Episode Rankings

  1. #1 Fan Favorite
    Two and a Half Men Season 5 Episode 1 - Large Birds, Spiders and Mom
    7.7/10(14 votes)

    #1 - Large Birds, Spiders and Mom

    S5:E1

    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.

    Director:Ted Wass
    Writer:Unknown

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  2. Two and a Half Men Season 5 Episode 2 - Media Room Slash Dungeon
    6.3/10(15 votes)

    #2 - Media Room Slash Dungeon

    S5:E2

    Charlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.

    Director:Ted Wass
    Writer:Unknown

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  3. Two and a Half Men Season 5 Episode 3 - Dum Diddy Dum Diddy Doo
    7.2/10(15 votes)

    #3 - Dum Diddy Dum Diddy Doo

    S5:E3

    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 Charlie's ex-girlfriends. Charlie's date backfires the following morning, when he ends up in court in front of the judge.

    Director:Ted Wass
    Writers:Lee Aronsohn, Chuck Lorre

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  4. Two and a Half Men Season 5 Episode 4 - City of Great Racks
    7.8/10(13 votes)

    #4 - City of Great Racks

    S5:E4

    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.

    Director:James Widdoes
    Writer:Unknown

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  5. Two and a Half Men Season 5 Episode 5 - Putting Swim Fins on a Cat
    7.6/10(13 votes)

    #5 - Putting Swim Fins on a Cat

    S5:E5

    Charlie has to come up with ways to keep his girlfriend's 4-year-old amused; Alan becomes a test subject.

    Director:James Widdoes
    Writer:Unknown

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  6. Two and a Half Men Season 5 Episode 6 - Help Daddy Find His Toenail
    7.3/10(16 votes)

    #6 - Help Daddy Find His Toenail

    S5:E6

    Charlie's girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.

    Director:James Widdoes
    Writer:Unknown

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  7. Two and a Half Men Season 5 Episode 7 - The Leather Gear Is in the Guest Room
    7.4/10(13 votes)

    #7 - The Leather Gear Is in the Guest Room

    S5:E7

    After Alan and Charlie have a fight about Alan's role in the house. Alan packs Jake up and moves in with his mother.

    Director:Ted Wass
    Writers:Lee Aronsohn, Chuck Lorre

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  8. Two and a Half Men Season 5 Episode 8 - Is There a Mrs. Waffles?
    8.0/10(13 votes)

    #8 - Is There a Mrs. Waffles?

    S5:E8

    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.

    Director:Ted Wass
    Writer:Unknown

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  9. Two and a Half Men Season 5 Episode 9 - Shoes, Hats, Pickle Jar Lids
    7.8/10(13 votes)

    #9 - Shoes, Hats, Pickle Jar Lids

    S5:E9

    Charlie fights his attraction for Teddy's daughter.

    Director:Jean Sagal
    Writer:Unknown

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  10. Two and a Half Men Season 5 Episode 10 - Kinda Like Necrophilia
    7.8/10(12 votes)

    #10 - Kinda Like Necrophilia

    S5:E10

    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.

    Director:Ted Wass
    Writer:Unknown

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  11. Two and a Half Men Season 5 Episode 11 - Meander to Your Dander
    7.9/10(11 votes)

    #11 - Meander to Your Dander

    S5:E11

    When Alan finds himself wanting to break up with a woman, Charlie offers his expertise.

    Director:James Widdoes
    Writer:Unknown

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  12. Two and a Half Men Season 5 Episode 12 - A Little Clammy and None Too Fresh
    7.6/10(12 votes)

    #12 - A Little Clammy and None Too Fresh

    S5:E12

    Rose returns from England, and plays nurse rather oddly for an ill Charlie.

    Director:James Widdoes
    Writer:Unknown

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  13. Two and a Half Men Season 5 Episode 13 - The Soil Is Moist
    7.5/10(11 votes)

    #13 - The Soil Is Moist

    S5:E13

    Alan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.

    Director:James Widdoes
    Writer:Unknown

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  14. Two and a Half Men Season 5 Episode 14 - Winky-Dink Time
    7.5/10(10 votes)

    #14 - Winky-Dink Time

    S5:E14

    Charlie double-dates with Jake and fixes Alan up with a hooker.

    Director:James Widdoes
    Writer:Unknown

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  15. Two and a Half Men Season 5 Episode 15 - Rough Night in Hump Junction
    7.9/10(12 votes)

    #15 - Rough Night in Hump Junction

    S5:E15

    Alan feels Charlie is unable to control his womanizing ways.

    Director:James Widdoes
    Writer:Unknown

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  16. Two and a Half Men Season 5 Episode 16 - Look at Me Mommy, I'm Pretty
    7.8/10(12 votes)

    #16 - Look at Me Mommy, I'm Pretty

    S5:E16

    Alan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister.

    Director:Joel Zwick
    Writer:Unknown

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  17. Two and a Half Men Season 5 Episode 17 - Fish in a Drawer
    7.2/10(17 votes)

    #17 - Fish in a Drawer

    S5:E17

    CSIs investigate a death at Charlie's house.

    Director:Jeff Melman
    Writer:Unknown

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  18. Two and a Half Men Season 5 Episode 18 - If My Hole Could Talk
    7.2/10(12 votes)

    #18 - If My Hole Could Talk

    S5:E18

    Charlie's attracted to an older self-help author. Alan and Jake clash over a project for school.

    Director:Jon Cryer
    Writer:Unknown

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  19. Two and a Half Men Season 5 Episode 19 - Waiting for the Right Snapper
    7.5/10(12 votes)

    #19 - Waiting for the Right Snapper

    S5:E19

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

    Director:Jeff Melman
    Writer:Unknown

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Season 5 Ratings Summary

"Large Birds, Spiders and Mom" is the best rated episode of "Two and a Half Men" season 5. It scored 7.7/10 based on 14 votes. Directed by Ted Wass and written by Unknown, it aired on 9/24/2007. This episode is rated 1.4 points higher than the second-best, "Media Room Slash Dungeon".