One of the most anarchic, squalid shows in TV history, It’s Always Sunny in Philadelphia is about to turn 20. It’s run for more seasons than any other live-action sitcom (although it should be noted those seasons were always short, and only got shorter), a surprising achievement for something that made its name plumbing the depths of a certain type of American psyche.
‘The Gang’, played by Glenn Howerton (Dennis), Charlie Day (Charlie), Rob Mac (Mac), Kaitlin Olson (Dee), and Danny Devito (Frank) are each alcoholic, sociopathic narcissists locked in a co-dependent quintuple, bumbling through various schemes they tire of by the end of each episode. Season one embraced the type of cringe comedy that was flourishing at the time (the UK Office was a stated reference point), and signalled its intentions by calling the first episode “The Gang Gets Racist”, but it was when DeVito entered in season two that the show found its feet.
It's Always Sunny in Philadelphia: Season 17
His character’s wealth opened the door for a larger scale of misadventure, and his desire to “live in filth and squalor” recalibrated Sunny into something closer in tone to an American The Young Ones. The core creative team of Mac, Day, and Howerton also realised having the sole female lead be a voice of reason wasn’t great, so Dee became as much of a scumbag as the rest of them.
It’s generally agreed upon amongst fans (to varying degrees) that seasons two through seven are Sunny’s high point, and it’s true the standard of comic anarchy was very high. This period is littered with classics like “Who Pooped the Bed?”, “The Nightman Cometh”, and “The D.E.N.N.I.S. System”.
But I’d argue the following nine seasons, while not as consistent as their predecessors, still hit impressive highs. In fact, my favourite three episodes, the three that really define the show, happened in this run. The show adapted to changing times, its stars’ ages, and its own longevity, becoming more meta, much weirder, and more willing to take creative risks.
Here are ten high points from Sunny’s latter half that number among the show’s best.
S08E05 “The Gang Gets Analyzed”
My personal all-time favourite episode of Sunny is one that could only happen this far into a show’s run. Each member of the gang is individually seen by Dee’s therapist, drawing on years of character-building in the process.
Mac casually tells her he gained and lost over 20kg in three months (Rob Mac really went through this physical change for the sake of the show, just over a much longer period of time). Frank reveals that as a child he was “shanghaied to a nitwit school” (this show really has a way with esoteric phrases), where he kissed a girl who had no lips, and made friends with a “frog kid”.
Dennis explains he’s been manipulating the gang for years (supplying Mac with “size pills” that are actually Ephedra, for example), and draws a picture of himself and the therapist:
S09E05 “Mac Day”
A lot of Mac’s early storylines revolved around his pursuit of women, but as the years went on, it became apparent he was a very, very closeted gay man. This episode introduces his cousin, Country Mac (Seann William Scott, one of many Sunny guest stars doing a great job playing it straight).
He’s everything Mac is not: out and proud, handy in a fight, calm and collected at all times. The episode ends with Frank flushing Country Mac’s ashes down a toilet after he unceremoniously drops dead.
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S11E03 “The Gang Hits the Slopes”
A good example of the show ramping up its absurdity, this whole episode seems to take place inside an 1980s ski field sex comedy. The characters all fall into place as various archetypes, the show not-so-subtly pointing out how gross those 80s sex comedies actually were.
S11E05 “Mac & Dennis Move to the Suburbs”
For many years, Sunny has implied to various degrees that Dennis is a serial killer and/or sex offender (yes, this is a comedy). His more unhinged side makes an appearance in this episode after he and Mac—both correctly identified by Frank as “city scum”—find themselves uniquely unsuited to suburban living, giving birth to this meme format in the process:
S11E10 “The Gang Goes to Hell: Part Two”
My second personal all-time fave finds The Gang trapped on board a sinking ship. Like many of the show’s best, it’s built around their five personalities butting up against each other in a single location. As per, this is when things get really weird. Here, that involves The Gang making engine noises with their mouths for an extended period, eating imaginary food, and eventually accepting their almost certain death.
S12E01 “The Gang Turns Black”
Another example of Sunny leaning into surrealism, this one finds them, well, turning Black. How and why that is, I won’t spoil, but I can say it involves a very funny cameo from Quantum Leap star Scott Bakula.
S12E06 “Hero or Hate Crime?”
This one is number three on my personal list, and again finds our five associates stuck with each other, this time joined by an arbiter. When a piano falls from a building above Mac, Frank alerts him by calling him a slur. This leads to an exploration of language and why certain things are unacceptable. Many bad words are spoken, and it all leads to a weirdly heartwarming conclusion. This is the episode where Mac finally comes out of the closet for good.
S13E10 “Mac Finds His Pride”
In what might be the show’s most divisive entry, Mac attempts to explain his queerness to Frank by staging an interpretive dance. The dance itself makes up the last third of the episode, and is played completely straight, initially funny because it’s so out of place, then becoming genuinely moving as it goes.
The episode ends with an emotional sucker punch from Danny DeVito, reminding us that he can be an incredible dramatic actor when he wants to be. It remains the sole time Sunny has been completely sincere, with no jokes to undercut Mac’s final moment of catharsis.
S15E01 “2020: A Year in Review”
A series of flashbacks reveals The Gang’s involvement with various incidents surrounding Donald Trump’s first term in office, from Rudy Giuliani’s runny hair dye to the Jan 6th riots.
S16E08 “Dennis Takes a Mental Health Day”
As well as Trump, Sunny has engaged with real-world specifics more and more, (largely things involving social media, and Dennis’ attempts to seduce politically-aware millennials), and this episode devotes itself to a very modern type of complication, involving apps, phones, and coffee orders.
It all builds to one of the show’s most intense, weird sequences. As hilarious as it is unsettling, it’s a perfect way to round off Sunny’s 16th season.
