The Best 'Two And A Half Men' Seasons, Ranked

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Updated April 23, 2024 36.7K views 12 items
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Vote up the show's best seasons.

In 2003, Two and a Half Men charmed viewers with its humorous take on the unconventional lives of Charlie Harper, his brother Alan, and Alan's son, Jake. Spanning twelve seasons, the show offered an eclectic mix of wit and heart as it tackled both comedic, and sometimes, serious issues faced by the characters. As with any great series, some seasons stand out more than others.

The best Two and a Half Men undoubtedly left a lasting impact on fans. It showcased tremendous writing and stellar performances from the cast led by Charlie Sheen, Jon Cryer, and Angus T. Jones in their respective roles. Each season added depth to the story and characters' relationships.

Season 3 maintains a perfect balance between comedy, drama and character development. Season 2 stands out with its clever storytelling and the contrast between Charlie and Alan in tackling love, parenthood, and sibling rivalry. Not to be overlooked, Season 6 seamlessly integrated Ashton Kutcher's character into the narrative, while maintaining the show's signature humor and charm. 

Two and a Half Men’s number of seasons consistently delivered high-quality entertainment. The top seasons in our list showcase just a fraction of what made this long-running sitcom such an adored part of television history.


 

  • Two and a Half Men - Season 3
    Photo: CBS
    1
    225 VOTES

    Two and a Half Men - Season 3

    The third season of Two and a Half Men premiered on September 19, 200,5 and contains 24 episodes. This season finds Jake going to boy-girl parties and starting to date.

    This season features several unforgettable episodes including: "Weekend in Bangkok with Two Olympic Gymnasts," "We Called It Mr. Pinky," and "That Pistol-Packin' Hermaphrodite."

    Memorable moments from Season 3 include:

    • Jake takes Viagra.
    • Charlie calls off his wedding to Mia.
    • Alan proposes to Kandi.
    225 votes
  • Two and a Half Men - Season 2
    Photo: CBS

    The second season of Two and a Half Men premiered on September 20, 2004, and contains 24 episodes. This season finds Alan getting back into the world of dating.

    This season features several unforgettable episodes including: "Back Off, Mary Poppins," "The Salmon Under My Sweater," and "Does This Smell Funny to You?."

    Memorable moments from Season 2 include:

    • Alan joins Charlie's men's group.
    • Charlie's conquests are exposed on the internet.
    • Jake is named "the chosen one".
    173 votes
  • Two and a Half Men - Season 6
    Photo: CBS
    3
    130 VOTES

    Two and a Half Men - Season 6

    The sixth season of Two and a Half Men premiered on September 22, 2008, and contains 24 episodes. This season finds Charlie maturing ever so slightly.

    This season features several unforgettable episodes including: "Taterhead is Our Love Child," "Pinocchio's Mouth," and "Baseball Was Better with Steroids."

    Memorable moments from Season 6 include:

    • Chelsea moves in with Charlie.
    • Mia returns.
    • Judith gives birth to Jake's sister.
    130 votes
  • Two and a Half Men - Season 5
    Photo: CBS
    4
    118 VOTES

    Two and a Half Men - Season 5

    The fifth season of Two and a Half Men premiered on September 24, 2007, and contains 19 episodes. This season was cut short as a result of the 2007–2008 Writers Guild of America strike.

    This season features several unforgettable episodes including: "Large Birds, Spiders and Mom," "The Soil is Moist," and "Fish in a Drawer."

    Memorable moments from Season 5 include:

    • Teddy is found dead.
    • Charlie and Angie breakup.
    • Charlie sets Alan up with a hooker.
    118 votes
  • Two and a Half Men - Season 4
    Photo: CBS
    5
    136 VOTES

    Two and a Half Men - Season 4

    The fourth season of Two and a Half Men premiered on September 18, 2006, and contains 24 episodes. This season finds Alan breaking down after his divorce from Kandi.

    This season features several unforgettable episodes including "Working for Caligula," "Corey's Been Dead for an Hour," and "Prostitutes and Gelato."

    Memorable moments from Season 4 include:

    • Charlie has a near-death experience.
    • Charlie and Alan find themselves in a love triangle with their hot neighbor.
    • Jake wins at the racetrack.
    136 votes
  • Two and a Half Men - Season 1
    Photo: CBS
    6
    181 VOTES

    Two and a Half Men - Season 1

    The first season of Two and a Half Men premiered on September 22, 2003, and contains 24 episodes. This season introduces viewers to Charlie Harper, his brother Alan, and his nephew Jake.

    This season features several unforgettable episodes including: "Most Chicks Won't Eat Veal," "If They Do Go Either Way, They're Usually Fake," and "Can You Feel My Finger?."

    Memorable moments from Season 1 include:

    • Alan and Jake move in with Charlie.
    • Berta quits because of Alan.
    • Charlie considers getting a vasectomy.
    181 votes
  • Two and a Half Men - Season 7
    Photo: CBS
    7
    119 VOTES

    Two and a Half Men - Season 7

    The seventh season of Two and a Half Men premiered on September 21, 2009, and contains 22 episodes. This season finds Charlie adjusting to being in a committed relationship.

    This season features several unforgettable episodes including: "818-jklpuzo," "For the Sake of the Child," and "This Is Not Gonna End Well."

    Memorable moments from Season 7 include:

    • Charlie and Berta smoke medical marijuana.
    • Chelsea breaks up with Charlie.
    • Charlie gets arrested.
    119 votes
  • Two and a Half Men - Season 8
    Photo: CBS
    8
    112 VOTES

    Two and a Half Men - Season 8

    The eighth season of Two and a Half Men premiered on September 20, 2010, and contains 16 episodes. This season includes a limited number of episodes due to Charlie Sheen being fired mid-season.

    This season features several unforgettable episodes including: "Three Girls and a Guy Named Bud," "Springtime on a Stick," and "That Darn Priest."

    Memorable moments from Season 8 include:

    • Charlie has an affair with Rose.
    • Alan meets Rose's "husband".
    • Alan sets Lyndsey's house on fire.
    112 votes
  • Two and a Half Men - Season 9
    Photo: CBS
    9
    142 VOTES

    Two and a Half Men - Season 9

    The ninth season of Two and a Half Men premiered September 19, 2011 and contains 24 episodes. This season introduces the character of Walden Schmidt, played by Ashton Kutcher.

    This season features several unforgettable episodes including: "Nice to Meet You, Walden Schmidt," "A Fishbowl Full of Glass Eyes," and "Oh Look! Al-Qaeda!."

    Memorable moments from Season 9 include:

    • Alan learns of Charlie's death.
    • Walden invites Alan to live with him. 
    • Berta becomes Walden's housekeeper.
    142 votes
  • Two and a Half Men - Season 10
    Photo: CBS
    10
    125 VOTES

    Two and a Half Men - Season 10

    The tenth season of Two and a Half Men premiered on September 27, 2012, and contains 23 episodes. This season finds the men exploring the possibility of marriage.

    This season features several unforgettable episodes including: "I Changed My Mind About the Milk," "Welcome to Alancrest," and "Cows, Prepare to be Tipped."

    Memorable moments from Season 10 include:

    • Lyndsey breaks up with Alan.
    • Jake gets involved in a mother-daughter love triangle.
    • Jake and Alan smoke Charlie's Cuban cigars.
    125 votes
  • Two and a Half Men - Season 12
    Photo: CBS
    11
    70 VOTES

    Two and a Half Men - Season 12

    The twelfth and final season of Two and a Half Men premiered on October 30, 2014, and contains 16 episodes. This season brings things full circle as Walden and Alan prepare to adopt a child.

    This season features several unforgettable episodes including: "The Ol' Mexican Spinach," "Bouncy, Bouncy, Bouncy, Lyndsey," and "Of Course He's Dead."

    Memorable moments in Season 12 include:

    • Walden proposes to Alan.
    • Alan proposes to Lyndsey.
    • Charlie's fate is revealed.
    70 votes
  • Two and a Half Men - Season 11
    Photo: CBS
    12
    131 VOTES

    Two and a Half Men - Season 11

    The eleventh season of Two and a Half Men premiered on September 26, 2013, and contains 22 episodes. This season introduces the character of Jenny Harper, played by Amber Tamblyn.

    This season features several unforgettable episodes including: "Nangnangnangnang," "Baseball. Boobs. Boobs. Baseball," and "Oh WALD-E, Good Times Ahead."

    Memorable moments in Season 11 include:

    • Charlie's long-lost daughter arrives at the house.
    • Alan proposes to Gretchen.
    • Gretchen leaves with her ex-husband.
    131 votes