The Best Seasons of 'Two And A Half Men'

List Rules
Vote up the show's best seasons.

All the seasons of Two And A Half Men were great, but which seasons really stood out? An Odd Couple story for the new millennium, the series begins as Alan and his son, Jake, move in with Alan's freewheeling brother, Charlie. Some of the most memorable episodes of Two And A Half Men come from different seasons, so picking the top season isn't easy. To determine once and for all what the best seasons of Two And A Half Men are, let's rank every Two And A Half Men season from best to worst.

Two And A Half Men is a television sitcom – created by Chuck Lorre – that is full of hilarious family dysfunction and relationship drama. Two And A Half Men premiered on CBS on September 22, 2003, and aired twelve seasons before concluding on February 19, 2015. Charlie Sheen left the show after his contract was terminated in the eighth season and Ashton Kutcher replaced him in the cast which included Jon Cryer and Angus T. Jones.

Vote up your favorite seasons of Two And A Half Men, and vote down any bad seasons that you really didn't enjoy, despite how much you loved any individual episodes. It can be painful to put one Two And A Half Men season over the other when there are so many good ones, which is why you can vote on however many seasons you like.


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

    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.
  • Two and a Half Men - Season 6
    Photo: CBS

    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.
  • 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".
  • Two and a Half Men - Season 5
    Photo: CBS

    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.