The Ten Best TWO AND A HALF MEN Episodes of Season Six

Welcome to a new Sitcom Tuesday! This week, we’re continuing our coverage of Two And A Half Men (2003-2015, CBS), which is currently available on DVD and Peacock!

Two And A Half Men stars CHARLIE SHEEN as Charlie, JON CRYER as Alan, and ANGUS T. JONES as Jake. With MARIN HINKLE as Judith, RYAN STILES as Herb, JENNIFER TAYLOR as Chelsea, CONCHATA FERRELL as Berta, and HOLLAND TAYLOR as Evelyn.

Two And A Half Men was still the most-watched sitcom during 2008-2009, once again earning Emmy nods for its two stars (Jon Cryer actually won), and Season Six mostly looks like business as usual, simply accelerating ongoing trends. However, this is the year where the series teeters over the line of passable sitcommery. This is because it’s moving away from its characters. That is, Six overindulges the rom-com, back-and-forth relationship-hopping that initially stemmed from a real part of the premise — two dysfunctional men trying to date — which contrasted the brothers’ depictions. But starting in Six, it feels like the regulars are not as actively inspiring the stories anymore and are instead merely vessels for plot. Although the prospect of Charlie seeking an actual grown-up romance has been building since Three, thereby making this serious attempt at monogamy a sign of growth, Six’s individual ideas in this arc seldom involve specific aspects of his persona. He might as well be any middle-aged doofus struggling to navigate a committed relationship, not the precise hedonistic lothario he’s premised to be. And he’s hindered significantly by the fact that his partner, Chelsea, has no personality and thus no way to be comedically or narratively helpful. This will prove to be the case with almost every future love interest on Men, and it’s a big concern as this series continues to devolve into an oversexed rom-com with women who exist more as narrative devices than true characters. Similarly, Six also has an unmotivated arc for Alan, as he briefly reconciles with Judith, who becomes pregnant with a child that may be either his or Herb’s — a soapy development that expedites the unfortunate trend of Alan supplanting Charlie as the series’ romantic rascal and primary comic force — a position that throws the show’s situation off-kilter, as we will see over the next few seasons. (Stay tuned…) Meanwhile, this year also claims another uptick in Men’s vulgarity, and though it sometimes seems like it’s still an extension of these characters, this kind of humor is now becoming so gratuitous that it’s beginning to unmoor itself from the leads — which is probably natural, given that they’re no longer as present in believable, motivated, character-revealing plots… Fortunately, despite this eroding quality, there are a handful of strong entries relative to the show’s baseline, so even with this decline, Six is MUCH better than what’s ahead.

 

01) Episode 116: “Taterhead Is Our Love Child” (Aired: 09/22/08)

Charlie fears an ex-girlfriend may be raising his child.

Teleplay by Mark Roberts & Don Foster & Jim Patterson | Story by Chuck Lorre & Lee Aronsohn | Directed by James Widdoes

Season Six opens on a memorable Charlie-focused entry that plays with a familiar idea often used for sitcom lotharios — the threat of an unknown child. It’s a notion that not only validates, inherently, the principal comic aspect of his characterization, but also the premised setup of him being an unideal or reluctant father — as he basically serves as a secondary parent to his nephew. In that regard, a story like this, albeit gimmicky and overused, is another reflection of the show’s situation, and by also using the central character well, it’s a routine example of solid sitcommery — from the last year where we can still expect to find it more often than not. Also, Rena Sofer guests and the funny Martin Mull debuts as Charlie’s recurring pharmacist.

02) Episode 117: “Pie Hole, Herb” (Aired: 09/29/08)

Charlie kicks out Alan over a money dispute.

Teleplay by Susan Beavers & Eddie Gorodetsky | Story by Chuck Lorre & Lee Aronsohn | Directed by James Widdoes

As discussed, Alan’s primary arc this season involves his brief reconciliation with Judith while she and Herb are on the rocks — a dalliance that possibly makes him the father of her second child, to which she gives birth at year’s end. It’s not a great story for anyone involved, because it doesn’t take advantage of their characterizations. But, thankfully, this pre-arc outing is decent on behalf of character, with funny moments for Ryan Stiles’ goofy Herb (who nevertheless has his best season due to this increased screen time) and a conflict between Charlie and Alan that, though indistinct, is an extension of the economic tension that has always existed in the premise, and will continue to increase, as Alan becomes branded more as a “mooch.”

03) Episode 118: “Damn You, Eggs Benedict” (Aired: 10/06/08)

Charlie takes up cooking and gives advice to both Alan and Jake.

Teleplay by Chuck Lorre & Lee Aronsohn | Story by Mark Roberts & Don Foster | Directed by Jean Sagal

One of the best ways this series can use Charlie is to have him negatively influence others. We’ve seen it often with Jake, at least in the early years, where Charlie’s role as “bachelor uncle” created conflict. But this offering has Charlie rubbing off on both Jake and Alan. As Charlie provides Jake with a flippant tip about drinking, he gives Alan advice on juggling two women — a move more typical of the Casanova brother, and indicative of something we’ve discussed, about how Alan eventually becomes the more serial dater, as Charlie seeks a more serious connection, thereby trading places and switching the series’ comic focus. So, this entry deploys Jake and Alan in relation to the still-centralized Charlie while also being narratively prescient.

04) Episode 124: “The Mooch At The Boo” (Aired: 11/24/08)

Jake is interested in the daughter of an overprotective former football player.

Teleplay by Susan Beavers & Eddie Gorodetsky | Story by Chuck Lorre & Lee Aronsohn | Directed by Jeff Melman

My choice for this season’s Most Valuable Episode (MVE), “The Mooch At The Boo” is the year’s best showing for a tentpole of the premise that’s seldom engaged with directly anymore — the idea that Charlie is the “bachelor uncle” proxy parent to Jake. It’s also the most enjoyable exhibit of Alan’s evolving characterization — and specifically, his comedic and narrative usage as it pertains to Charlie. In the first place, the A-story finds Jake wanting to date the neighbor girl (played by Tinashe), the daughter of former NFL star Jerome (Michael Clarke Duncan), a strong laugh-getter who returns later in the year. It’s up to Charlie — the known scoundrel — to mollify the stern and menacing Jerome and ease his mind regarding Jake’s intentions (which are typical for a teen, but especially concerning given his uncle’s influence). Their scenes are a hoot — some of the funniest of the season. Speaking of which, the subplot with Alan is incredibly funny as well, as he picks up a woman (Bellamy Young) by pretending that he owns a home in Malibu, which, of course, really belongs to his out-of-town mother. This plays to the recurring joke that Alan is a leech on his family, and someone who’s willing to scheme and manipulate for nookie — much more so than his brother, who has a reputation for bad behavior but doesn’t have to try so hard. The climax, although brought about by the unmotivated and unoriginal twist of the woman being a con artist, sees Alan left with nothing to wear but one of his mother’s dresses, and it’s hilarious, showcasing his shifting role as the series’ boldest comic player. And that’s why, in displaying major aspects of both character and premise, along with the sensibility of this particular year, there’s no better example of sitcommery here in Season Six.

05) Episode 127: “Thank God For Scoliosis” (Aired: 01/12/09)

Alan is attracted to his former receptionist, while Charlie and Jake compete over a woman.

Teleplay by Chuck Lorre & Mark Roberts | Story by Eddie Gorodetsky & Jim Patterson | Directed by Jeff Melman

This entry notably features the first of two guest appearances by Taxi alum Carol Kane as the mother of Alan’s former receptionist Melissa (Kelly Stables), who becomes his love interest here. Kane is always a delight, and I can’t deny that her sheer presence helps elevate what would otherwise be a forgettable story about loser Alan and his never-ending relationship troubles. Beyond Kane, however, there’s an amusing subplot where Charlie and Jake compete for the affections of a pretty waitress who is somewhere between them in age and seems to show an interest in both. It’s maybe a bit contrived, but it works well with the Charlie characterization and the premised construct of him serving as Jake’s bad influence proxy parent.

06) Episode 129: “David Copperfield Slipped Me A Roofie” (Aired: 02/02/09)

Alan’s girlfriend believes his family mistreats him.

Teleplay by Don Foster & Jim Patterson | Story by Mark Roberts | Directed by Jeff Melman

Alan’s romance with Melissa concludes in this laugh-heavy offering that again features Carol Kane as her mother, with whom Alan winds up having a drug-fueled tryst. It’s typical Men, with a hyper-sexuality that is both obvious and yet unexpectedly direct — initially a manifestation of Charlie’s character (but here, Alan’s) that has increased over time and is obviously a series-defining attribute, now beyond the regulars’ depictions that once enabled it. Again, if not for Kane — and a funny teleplay that makes fun of Alan’s placement in the ensemble — this would be a foreboding sample of how Alan’s changing usage dilutes the situation. But with those favorable attributes, it’s a memorable reflection of the series’ evolving identity in this era.

07) Episode 131: “She’ll Still Be Dead At Halftime” (Aired: 03/02/09)

Charlie must remove a half-naked woman from his room before Chelsea returns.

Teleplay by Don Foster & Eddie Gorodetsky | Story by Mark Roberts | Directed by Jeff Melman

This very funny entry boasts a classically farcical logline where Charlie, fearing that his out-of-town girlfriend is cheating on him, brings another woman back to his place and then regrets it… especially when said girlfriend, Chelsea (Jennifer Taylor), returns home on short notice. Now, Charlie and Alan must get the strange lady out before Chelsea sees her — a mission complicated by the fact that this strange lady has passed out… Okay, this setup will always be amusing, for it invites reliable slapstick comedy. But it’s also directly attached to Charlie’s characterization, hinged on him being torn between his old floozy ways and his current attempt at monogamy. So, although this is an idea-driven notion, it’s also an exploration of character — and, actually, it’s easily the funniest of all the Chelsea shows (for it doesn’t rely on her to do much of anything but be an obstacle… which is all she can be, given her lack of definition).

08) Episode 134: “The Two Finger Rule” (Aired: 03/30/09)

Charlie and Alan commiserate with their guy friends.

Teleplay by Susan Beavers & Eddie Gorodetsky & Jim Patterson | Story by Chuck Lorre & Lee Aronsohn | Directed by James Widdoes

Yet another offering that’s become one of Men’s most popular — and a testament to Season Six’s handful of big-idea gems — this MVE contender is the best version of a template that the series will try a few more times to recreate: the “hangout” or “male bonding” show. This is a formula that basically congregates all the adult males together — here, that’s Charlie, Alan, Jerome, Herb, and Gordon the pizza boy (J.D. Walsh) — to commiserate about their women. It’s a chance for established characterizations to bounce off each other in an extremely jokey context, and for the series to display both its relationship-geared narrative bent and its overarching tonal identity via a focus on caricatured masculinity, for no other major sitcom in 2009 is as centered around the male perspective (for better and for worse), with its laughs and its storytelling reiterating that attitude. And fortunately, there’s still some affiliation to character at this point in the run too… which is rapidly becoming less and less true.

09) Episode 136: “Above Exalted Cyclops” (Aired: 04/27/09)

Rose befriends Chelsea and begins dating Alan.

Teleplay by Don Foster & Eddie Gorodetsky | Story by Chuck Lorre & Lee Aronsohn | Directed by James Widdoes

If you’ve been following this coverage, you know that I’m not a huge fan of the Rose character, for I think she’s too one-dimensional to be narratively reliable, especially as Charlie’s potential one true love (which is implied). But I appreciate this excursion for better integrating her within the ensemble, as she befriends Chelsea and starts seeing Alan — whose utilization here, as he begins a largely sexual relationship with one of Charlie’s former conquests, symbolizes the role reversal that’s been gradually occurring this season between the two brothers, and will really come to be obvious in the final few years of Charlie’s tenure. Accordingly, this is more dynamic and revealing for character than most of Men’s Rose-heavy samples.

10) Episode 139: “Baseball Was Better With Steroids” (Aired: 05/18/09)

Charlie is romantically conflicted and Judith goes into labor with a baby that may be Alan’s.

Teleplay by Chuck Lorre & Lee Aronsohn | Story by Mark Roberts & Susan Beavers | Directed by Lee Aronsohn

Season Six ends with a Big Event that I seriously considered excluding from this list. I don’t like its clichéd cliffhanger with Charlie caught between Mia and Chelsea and some of the familiar “chaos for chaos’ sake” surrounding the events of Judith’s labor. However, it’s one of the funniest outings for Ryan Stiles’ Herb — who’s well-featured this year as a result of the otherwise unfortunate triangle arc for him, Alan, and Judith — and I think this teleplay actually manages to pack in enough laughs so that, from a bird’s eye view, it feels like this episode has to be here, for it’s the climax of an important storyline that is unique to this season, and there’s no other half hour in the arc that’s as enjoyable. (Joel Murray and Ken Lerner appear.)

 

Other notable episodes that merit mention include: “Good Morning, Mrs. Butterworth,” a silly show where Charlie and Alan are nevertheless well-contrasted in such a way that it was worth considering for the above list. I’ll also take this space to cite two entries in the Alan/Judith/Herb arc, “It’s Always Nazi Week” and “Best H.O. Money Can Buy,” along with “The Flavin’ And The Mavin,” which is well-predicated on Charlie’s character, “A Jock Strap In Hell,” which guests Alicia Witt (from Cybill) and calls back to a fine installment from Season Two, “The Devil’s Lube,” which guests Emilio Estevez and tries to be thoughtful about Charlie, and “Hello, I Am Alan Cousteau,” which is the year’s best showing for Evelyn.

 

*** The MVE Award for the Best Episode from Season Six of Two And A Half Men goes to…

“The Mooch At The Boo”

 

 

Come back next week for Season Seven! And stay tuned for a new Wildcard Wednesday!

4 thoughts on “The Ten Best TWO AND A HALF MEN Episodes of Season Six

    • Hi, Nat! Thanks for reading and commenting.

      I agree — and he was also a fresh way to link Charlie and Jake in story and hopefully reiterate a key part of the premise.

  1. I like seeing more of Herb this year but I dont like Chelsea either. She’s hot but always such a buzzkill. Her seasons are not my favorites!

    • Hi, Brad! Thanks for reading and commenting.

      I share your disfavor for Chelsea as a comedic character — she wasn’t defined well for laughs or story!

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