From 2003-2015, Chuck Lorre’s CBS sitcom Two and a Half Men captured the hearts of many Americans. The mid-2000s hit starring Charlie Sheen as Charlie Harper, Jon Cryer as Alan Harper, Angus T. Jones as Jake, and eventually Ashton Kutcher as Walden Schmidt still airs 365 days a year on local cable and is syndicated on many TV networks, including Paramount, TV Land and IFC. The show is also available to stream in its entirety on Peacock. There are endless ways to watch this show, which speaks to its lasting popularity, even eight years after the final episode aired.
Full disclosure: I hadn’t seen the show until 2021. I was back at Kent State University during my final semester of college, and I was looking for a new show to get into. More than one person recommended Two and a Half Men to me, and I had seen particle clips of the show from when my parents were watching it, so I gave it a try.
I was hooked from episode one.
Now, it did take me almost a FULL YEAR (no, I am clearly not a binge-watcher!) to complete the series. I started watching in January 2021 and finished around Christmas, but the more I watched, the more excited I was to watch the next episode.
After taking about a year off from watching the show, I recently began re-watching the show through re-runs on various channels, and I’ve been laughing at the show MORE the second and third time I’ve seen episodes. Two and a Half Men is truly the perfect mix of writing, characters, and personality. The dynamic between Charlie and Alan reminds me of the dynamic at my house growing up, and it makes the show that much more relatable.
Every season of the show wasn’t necessarily sunshine and rainbow, though, which is why ranking every season of the show was more difficult than expected.
- Season 9
This was the first season Kutcher took over for Sheen after Sheen left the show due to various drinking issues and public comments shaming Lorre. In the storyline, Season 9 kicks off with Charlie’s funeral. In the show, Charlie dies after getting run over by a train while in Paris with his stalker/girlfriend Rose (They went to Paris together at the end of Season 8). Now with Charlie gone, his mother Evelin — a real estate agent — is selling his massive beach house. Walden makes his debut by coming up to the beach house and scaring Alan while holding Charlie’s urn, causing the late Harper’s ashes to drop all over the floor, signaling a new era in the show.
Walden reveals he was trying to commit suicide on the beach because he didn’t have anything to live for after his wife of a decade-plus Bridget divorced him because he acted too much like a child. When Walden reveals he is a tech wizard with millions of dollars with his own company, he buys Charlie’s house and lets Alan live with him, as Alan promises to help him recover from his divorce.
My biggest gripe with this season was it had no direction. Lorre did not have an exact idea of where he wanted to take the Walden character. Everything was sort of thrown together, and Walden wasn’t established. The worst episode of the series also takes place this season. Episode 12 of the season, “One False Move, Zimbabwe!” is the season’s Christmas episode and features the first appearance of Walden’s mother, who reveals Walden has a brother who is a gorilla…yes a gorilla! At the end of the episode, Alan, Walden and his mother go visit Walden’s “brother” at the zoo.
Walden’s brother is never mentioned again, and the whole idea just didn’t make any sense at all. While the end of the season provides direction for the rest of the series such as Walden going from long rail to short hair, Alan reestablishing his relationship with his girlfriend Lyndsey and Jake departing for the military, a lot of the episodes in Season 9 are mostly filler, and some were just not up to the quality the previous eight seasons provided.
- Season 11
Ironically, the second worst season of the show happens to be the penultimate season of the series. Just like with season 9, season 11 had some new characters to establish. Two and a Half Men had turned into Two Men and a Women, as Amber Tamblyn (playing the character of Jenny, Charlie’s long-lost daughter), replaced Jake as the third co-star as Jones left the show due to religious reasons. Jenny is the lesbian version of her dad, as the writers tried to recreate the Charlie Harper character, but it didn’t come off well. The season also introduces new characters to the show, Barry and Nicole. Nicole is a former friend of Walden’s, who is running her own sophomore company, with Berry as her assistant. Though Walen tries to get together with Nicole, their relationship is a short stint and so is Berry, though he does get along with Jenny.
This season was also more primarily focused on Alan than Walen. Alan becomes jealous Lyndsey is seeing another man after they break up. Alan spots the guy — known as Larry — while working out in the gym. Larry and Alan begin talking and become friends, and Alan takes on a persona known as Jeff Strongman to hide his true identity from Larry. By the end of the season, it’s Larry and Lyndsey’s wedding day, and Alan is Larry’s best man, but when Alan reveals his true identity, the wedding does not happen. Also during the season, Alan, as Jeff Strongman, begins to date Larry’s sister, Gretchen, who is the carbon copy of Alan, but when she finds out Alan’s true identity, she dumps him before Larry and Lindsey’s wedding. If it sounds like a bunch of characters with not a lot happening and weird, random storylines, that’s exactly what Season 11 was.
- Season 12
The final season of Two and a Half Men wasn’t the best and offered one of the strangest storylines throughout the entire series. The season opener, “The Ol’ Mexican Spinach”, see’s Walden suffer a heart attack on Halloween and decides to change his lifestyle. As part of that change, he wants to adopt a child, but in order to adopt, Walden needs to have a spouse. This leads to Walden and Alan getting married and pretending to be a gay couple. Eventually, Walden and Alan adopt Louis, and both Alan and Walden both date Louis’ social worker, Ms. McMartin, who finds out Alan and Walden aren’t gay. In the penultimate episode of the series, “Don’t Give a Monkey a Gun”, Alan proposes to Lyndsey, and she accepts, wrapping up that storyline.
The final episode of the series, a two-parter titled “Of Course He’s Dead”, see’s Rose reveal Charlie is not dead, and she kept him in a well for years. Clues are left around the house that Charlie is coming back to kill Alan and Walen. There are many cameos in the series finale (which plays way too much to the ending of the series), including a return from Jake and Arnold Schwarzenegger. The ending of the show sees an actor that looks like Charlie from the back being squashed by Charlie’s piano.
The finale was not the worst series finale in sitcom history, but it struck out on ample opportunities in my opinion. The non-involvement of Herb, who began the show as Jake’s pediatrician, turned into Judith’s (Alan’s ex-wife) wife (and eventually her ex-wife) bothered me, as he had such a prominent role as a side character throughout the series. Also, not having Louis involved in any aspect made the whole last season feel pointless. In that regard, the finale fell short, and it drops this season pretty low down the list.
- Season 10
Season 10 wasn’t spectacular by any means, but it was far and away the best season in the Walden era because it actually had a storyline to follow. The season opener, “I Changed My Mind About the Milk”, sets the stage for the season as Walden ends his relationship with Zoey, his first relationship post-Bridget and Alan facetimes Jake from the Airforce, signaling Jake will mostly be gone from the season. Jake eventually comes home twice during the season — once with a young girl named Missy (played by Miley Cyrus) and with a 30-year-old (who he dumps at the end of the episode).
This season also sees Walden date Rose (going against Alan’s advice). Once breaking away from Rose, Walden believes he can not find love because he’s rich, so he starts dating a woman named Kate and takes on the persona of Sam Wilson, a low-income individual.
This season gave Walden a defined character trait and set him up for future storylines down the road, as well as progressing the relationship between Alan and Lyndsey. The season ends with Alan taking Jake on a father-son trip before Jake leaves for Japan.
- Season 8
The last season with Charlie before Walden comes into the picture is a hard one to grade because it’s technically incomplete. The season kicks off with Charlie recovering from his break-up with long-time girlfriend Chelsea (We’ll get to that later). He gets back together with his old girlfriend Courtney for a couple of episodes before breaking up with her and realizing he’s in love with Rose. However, Charlie’s too late, as Rose is set to marry Manny Quinn. Charlie doesn’t believe Rose and goes to the church where the wedding takes place and sees Rose marry Manny, though it turns out Manny is a mannequin and a ploy for Rose to get back together with Charlie.
Alan has some of the most natural progression of his character in the series this season. He moves in with Lyndsey while also getting back together with Melissa at Charlie’s house. Alan and Melissa eventually break up after Melissa realizes Alan is seeing another woman on the side. Alan then ends up burning down Lyndsey’s house, and Lyndsey, Alan, Jake, and Lyndsey’s son Eldrige — Jake’s best friend — move into Charlie’s beach house together, where it is revealed Lyndsey is a former porn star.
At the end of the season, Charlie tries to convince Rose to break up with Manny and date him while Alan runs a Ponzi scheme to get money out of his family members. When Rose finds out about it, Alan finds out about Rose’s mannequin but doesn’t tell Charlie. The season ends with the mannequin falling on Charlie in Rose’s closet when Charlie goes upstairs to get her jacket.
This season has some of the funniest episodes in the series and moments, including when Jake and Eldridge perform stunts in “Looking’ for Japanese Subs” when Berta leaves town for a family reunion, and Charlie falls in love with her replacement for the weekend and when the boys try to set up their mother with Charlie’s pharmacist Russell. The episodes are classics, but the incompleteness of the series led to the ending of the character of Charlie Harper and knowing what proceeds after it dies down this season. If the events of Seasons 9-12 didn’t happen, this season would be in the Top 5.
- Season 2
Season 2 is just one of those seasons in my opinion. Good, comedy episodes, but there isn’t one that stands out, as the season mostly just built on the foundation set in Season 1. What holds this season back is the lack of character progression for all three of Charlie, Alan, and Jake at this point in the series, as it’s mostly a rinse-and-repeat from Season 1.
- Season 1
We go all the way back to the beginning with the next season on the countdown. Great sitcoms do not always start off great. Sometimes, shows get off to slow starts, and the first season becomes unforgettable. That’s not necessarily the case for Two and a Half Men. There are a handful of memorable episodes from Season 1, including the second episode, “Big Flappy Bastards”, where Jake lets seagulls into the beach house. Watching the series back, I forgot about the initial storyline that the reason why Alan and Judith divorced is that Judith thought she was a lesbian (which was then seemingly dropped out of nowhere in Season 2). It was a good introduction to the show, but there are better seasons.
- Season 5
As we get to the Top 5 of the countdown, Seasons 4 and 5 for me could be flopped. They’re equally as funny. I put Season 5 here because Season 4 has more memorable episodes. The season premiere of Season 5, “Large Birds, Spiders and Mom”, see’s Charlie and Alan attempting to get Jake ready for his first day of middle school and features one of the more classic scenes from the series when the bus is pulling away, and we see Jake crammed into the back of the bus window with a bunch of kids on top of him.
This season begins to shift the main storyline on Charlie again, as he dates a woman named Linda, who is a judge. By the end of the season, they break up, and Charlie is back to dating whoever he wants. This is also the season he begins his success as a kid’s songwriter, with the episode “Is There a Mrs. Waffles?”
The most memorable episode from the season happens in episode 17. “Fish in a Drawer” sees Evelyn’s husband Teddy pass away mysteriously in Charlie’s bed at the reception of their wedding. This leads to a CSI-like investigation to find out who killed Teddy.
The last notable portion of Season 5 is the turn of Jake, who turns from a cute young lad into a dumb, mischievous young man, including when he sneaks out of the house to go to a concert in “Help Daddy Find His Toenail”.
- Season 4
The first episode of the season is a time-lapse and picks up right where Season 3 left off (Two seasons not on the list yet do the same later on). I always like when shows do that because it shows the ratings are so good the show was renewed, and it often features long-term storytelling. The time-lapse shows Alan’s relationship with Kandi (who we’ll get to in Season 3).
Now, Alan is back at Charlie’s house, divorced a second time, and trying to figure out his way of life again. The opening episode, “Working for Caligula”, also sees Charlie return to his bachelor ways after dumping Mia (We’ll also get to this in Season 3). Season 4 has so many good tiny storylines/episodes, including Charlie seeing his dead father while almost drowning in the ocean, Alan trying to get the dog back he and Kandi bought together, Charlie dating a girl who’s a younger version of his mother, Rose moving to London, and Alan dating Berta’s daughter.
- Season 3
The first season that followed a true storyline in the series, Season 3 holds a special place in my heart. The season revolves around both men dating women for longer than a one-night stand. Charlie dates Mia, who is a good, young-hearted woman who tries to change Charlie’s habits of drinking, smoking, and gambling. They meet at a dance studio, where Mia is an instructor. Charlie tries to impress her by having Jake do ballet lessons.
Alan meanwhile dates Kandi, a 22-year-old dumb girl who just likes Alan for his work in bed. Eventually, in the season finale, all four of them go to Vegas, where Charlie and Mia are going to get married. However, when Mia tells Charlie when they’re married, Alan and Jake are going to have to move out, and Charlie surprisingly dumps Mia.
Meanwhile, Alan sees an opportunity since they’re already in Vegas to marry Kandi, and that’s where the events of Season 4 pick up, with it being revealed Alan won the lottery in Vegas the night they got married.
Kandi and Mia both played their roles perfectly in this season, and the dynamic between them and their lovers starts to take Two and a Half Men to new levels in this season. The first episode of the season, “Weekend in Bangkok With Two Olympic Gymnasts”, is one of my favorite episodes throughout its entire run. Alan falls off the roof while fixing the satellite for the TV, causing Charlie to watch Jake the whole weekend in a hilarious 30-minute episode.
- Season 7
Season 7 and Season 6 are pretty much tied, though Season 6 has my favorite episode in the whole series, so that’s why I give it the nod. If you could not tell already, I love the character of Charlie Harper. He’s one of my favorite characters of all time in any sitcom, and these two seasons are mostly about Charlie.
Season 7 kicks off where Season 6 ended: Alan and Charlie are at a coffee shop. Alan is working on a novel when Mia walks in to Charlie’s surprise. At the opening of Season 7, Charlie has to decide between his former love (Mia) and his current love (Chelsea). He eventually chooses Chelsea, and Season 7 ends with Charlie and Chelsea breaking up at Chelsea’s birthday party.
I love shows with great stories, and Season 7 of Two and a Half Men told the story of Chelsea and Charlie. We, the viewer, were rooting for Charlie to finally be a good boy and settle down, but he just never could.
- Season 6
My favorite season of the entire series features Charlie beginning his two-season and longest relationship with Chelsea, and Alan getting back together with Judith for one night while also having unprotected sex and thinking he’s the father when Judith announces she and Herb are pregnant.
The season finale, “Baseball Was Better With Steroids”, encompasses everything the series is and is my favorite episode. Alan, Jake, Charlie, Judith, Chelsea, and Herb all get the spotlight as Judith goes into labor. Alan also encompasses his relationship with Melissa, who now is working at the hospital where Judith is at. The season ends with Charlie and Alan at the coffee shop when Mia shows up, as mentioned above.
No matter if you were a fan of the Charlie part of the series or Walden, Two and a Half Men did its job and made people laugh. Ultimately, ranking the seasons was harder than I had originally guessed. You could talk me into flipping a lot of the order of my rankings. The show was an all-time classic.