The thing to keep in mind about the version of Aaron Sorkin that created and ran the two-season ABC dramedy Sports Night, which premiered 20 years ago this week, is this: He was not yet a name. A respected playwright, sure; an accomplished screenwriter, definitely. But he was still relatively young to both of those fields — his breakthrough play, A Few Good Men, had debuted less than a decade earlier, and its film adaptation (his first screenplay) premiered in 1992. He was an outright newcomer to television, and as such, he did something totally understandable with Sports Night: He filled it to the brim with ideas, perhaps more than it needed, perhaps because he didn’t know how many shots he would get.
Needless to say, he got many more, and thus Sports Night has taken on an interesting position within his body of work: It’s something of a Patient Zero for Sorkin World. The show concerns the behind-the-scenes workings of a SportsCenter-style nightly cable sports-news show, anchored by cocky buddies Casey McCall (Peter Krause) and Dan Rydell (Josh Charles); produced by brilliant but flighty Dana Whitaker (Felicity Huffman) with the help of tough, bright Natalie Hurley (Sabrina Lloyd) and charismatically nerdy Jeremy Goodwin (Joshua Malina); all under the supervision of wise managing editor Isaac Jaffe (Robert Guillaume). Themes and threads of the show reappear in the films, plays, and shows Sorkin wrote in the two decades that followed. Those echoes became clearer while revisiting the series to rank its 45 episodes, as did the subtler shifts in its style (and, often consequently, quality). And thus, our highly subjective but totally accurate ordering of those episodes, from worst to best.
45. “Dear Louise” (Season 1, Episode 7)
“Dear Louise” was the first of two episodes narrated by Jeremy, a newcomer to the newsroom, in the form of a letter to his deaf sister. While this presumed tribute to M*A*S*H is an effective method of backfilling — Jeremy is able to give its recipient, and thus the television audience, everyone’s biography, as well as the history of the show and its network, CSC — the execution is saccharine, all thoughtful voice-over accompanied by plinky guitar and Hallmark sentiments (“I’ve only been here three months but it already feels like home to me”), clumsy internal-monologuing (“I felt terrible for suggesting the story wasn’t important enough”), and, worst of all, the kind of character description that’s usually, wisely kept to the stage directions of a script (“The result is an irresistible combination of brilliance inside the office, and something a little less than brilliance anywhere outside of it”). Even the worst episode of Sports Night has its moments, and this one certainly does — Casey trying and failing to razz Dana’s newish boyfriend Gordon takes a funny turn — but overall, this feels like someone at the network suggested Sorkin write “Dear Louise” to catch up latecomers to the show.
44. “Pilot” (Season 1, Episode 1)
The debut episodes for character-based sitcoms are traditionally rough going (ever sit through the first Friends? Good heavens), because when your laughs and tears are based on how these people respond to situations and each other, you first have to get to know these people. But the first episode of Sports Night is even shakier than most, because Sorkin and Thomas Schlamme (who directed it, and much of the subsequent run) hadn’t yet nailed down the tone. That means it veers into too-hyper, too-broad scenes like Jeremy’s Big Bang Theory–worthy interview, which is capped off with wild cheering and wooing from the studio audience/laugh-track hybrid. That sound of laughter is a big problem throughout season one, especially early on — a network directive that is particularly out of place on a show that’s not really “laugh out loud” material anyway (it’s more of a “chuckle lightly” and “grin at the cleverness” sort of endeavor), and the laugh track is often awkwardly layered atop the dialogue because the actors aren’t holding for laughs, because why would they. Throw in some reallllllly on-the-nose expositional dialogue (“I love producing Sports Night,” Dana announces. “I live from 11 to midnight”) and you’ve got an inaugural outing that basically requires a, “No, really, stick with it,” assurance when recommended to friends.
43. “How Are Things in Glocca Morra?” (Season 1, Episode 17)
The second (and thankfully last) “Dear Louise” episode isn’t nearly as obnoxious — there’s less of the narration, and it’s doing way less heavy lifting. But it’s still an unnecessary addition to an otherwise key moment between Dana and boyfriend Gordon, who has been complaining frequently that she puts the show ahead of their relationship — and its outcome is complicated by the fact that, unbeknownst to Dana, Gordon is also sleeping with Sally, the producer of the network’s 2 a.m. “West Coast update,” who ends up taking over the show. The emotional fallout of that decision is clear; we don’t need Jeremy’s voice-over assuring us, “I have a hunch it’s gonna be quite a while before Casey and Dana are quite the same with each other.” (Some unrelated trivia: The title of this episode comes from its original script, which featured a running gag in which Isaac was attempting to recall the lyrics to the title song. When Gulliaume had his stroke, he was hastily written out of the episode, but that showtune thread was revived for the season two episode “Celebrities.”)
42. “The Quality of Mercy at 29K” (Season 1, Episode 9)
An episode full of wonderful moments — Dana’s call to the Lion King box office, attempting to procure tickets for that same day (“He’s laughing … now he’s telling his friends … now they’re laughing … and he hung up”); her subsequent religious experience there (“It was like … church. I didn’t know we could do that. Did you know we could do that?”); Isaac’s explanation of why he no longer gives money to the Democratic Party (“You get your heart broken often enough, you learn your lesson”); Natalie’s response to Dan’s charity inquiry (“Well, my portfolio’s pretty much tied up in food and shelter”) — is semi-wrecked by the clumsiness of its closing minutes, in which Dan, who has been trying to focus his charitable giving, is conveniently confronted by a homeless person in his office, and to put it mildly, does not respond in a believable way. And then there’s a needle-drop for “The Weight,” which is unsubtle even by this show’s standards.
41. “When Something Wicked This Way Comes” (Season 2, Episode 2)
The second episode of the second season introduces one of the series’ best occasional characters: Sam Donovan, the “gunslinger” fixer who comes in (at the behest of Isaac, not the network) and gets into everyone’s heads. He’s a marvelous character, unpredictably written and enigmatically played by the great William H. Macy (also, not incidentally, Huffman’s husband). Also, “Dan has a crush on Hillary Clinton” sounds like either a cheap joke or a prototypical Sorkin the Liberal log line, but it’s neither; it’s a funny subplot in which Dan’s overworked self-confidence is the target. So why is this episode so low? Because it is the episode that introduces “the dating plan,” wherein Dana and Casey, whom we spent the entire first season waiting for Sorkin to put together — a union that seemed entirely assured by the second season debut — is delayed by Dana’s impossible-to-swallow “epiphany” that in order for the pair to “have a clear shot at this,” he has to date other women for six months. It’s a plot thread that would eat up way too much of the second season before shutting down their relationship entirely; Dana/Casey shippers still steam at its mention.
40. “Shoe Money Tonight” (Season 1, Episode 10)
Sorkin loves a good poker game; his directorial debut Molly’s Game is built around the inherent drama of high-stakes card play. So when Dan and Casey have to cancel their Atlantic City trip to cover the 2 a.m. show, we get to watch these characters entertainingly go at each other around the card table, while the hand-off of the 11 p.m. anchors to the 2 a.m. producer creates some sharp tension (nicely captured in the visual of Brenda Strong’s Sally towering over Huffman’s Dana). But there’s a strange ugliness to the Jeremy/Natalie subplot in this episode — in the way he seems to delight in humiliating her at the table, and the big mansplainy speech about how he’ll never hurt her, which sticks a bit in retrospect considering how he ultimately, y’know, did.
39. “A Girl Named Pixley” (Season 2, Episode 9)
“Casey’s out with Pixley?” Isaac asks. “Do you suppose the two of them could be any more white?” The official beginning of the “dating plan” does little more than underline its fundamental silliness — and make Casey deeply unsympathetic in the process. “A Girl Named Pixley” also includes one of the show’s rather frequent statement–question–reversal-of-statement joke constructions (“I wasn’t mean to Pixley!” “How did it go?” “I was totally mean to Pixley”); sole writing credit for this episode goes to David Walpert, and this is one of the rare moments in the second season where you can see another writer, covering for Sorkin (who was simultaneously writing and running The West Wing), trying to write like him. And there’s just something unseemly about the way Sorkin will so often show his characters chuckling at each other’s jokes or remarking on their wittiness; it’s one of the things that ended up sinking Studio 60, a show full of people talking about how brave, brilliant, and hilarious a terrible sketch-comedy show was.
38. “The Hungry and the Hunted” (Season 1, Episode 3)
Sorkin’s theatrical roots are particularly evident in the show’s earliest episodes, which often seem structured for the specific purpose of setting up a character’s hand-crafted, poignantly revealing show-stopper monologue. That inclination isn’t necessarily a bad thing – it comes together nicely in the second episode, “The Apology.” But it hurts the show’s momentum somewhat to have another episode, so similar in construction and tone, follow suit. This time, it’s an earnest anti-hunting diatribe by Jeremy, who mildly resists the assignment for CSC’s outdoor show (“I don’t know anything about hunting. I’ve never hunted. I’ve got a deli on the corner and they deliver 24 hours, so…”) but goes along so as not to rock the boat, only to voice his objections after the fact. “What we did wasn’t food, it wasn’t shelter, and it sure wasn’t sports,” he tells Isaac and Dana. “It was just mean!” Fair enough! But this kind of overtly political, super-serious material would find a much more comfortable home on The West Wing the following season.
37. “The Giants Win the Pennant, the Giants Win the Pennant!” (Season 2, Episode 10)
So this is the episode where Dana finally realizes what we’ve all known for the previous eight episodes: “The dating plan sucks.” That’s all well and good; the trouble with this one is how it explicitly paints Dana as kinda-crazy, particularly when Dan comes into her office and tells her things like, “All I’ve seen you do is hide behind this psychotic behavior dressed up as cute.” (This kind of professional-ladies-be-crazy characterization that would end up coming to an ugly head on The Newsroom.) That said, the imagery of the closing scene – in which Dana shows up at the neighborhood bar, looks around, and discovers Casey just left with Pixley – is potent. And it’s clear that, by now, they know all they have to do is give Huffman a close-up, as she weighs this information while acting like everything’s fine, and she’ll play a symphony.
36. “Intellectual Property” (Season 1, Episode 4)
To this day, whenever anyone sings “Happy Birthday,” I think of Isaac’s incredulous response to Dan discovering the network has to pay royalties to its songwriters: “It took two people to write that song?” That B-plot, in which Dan decides he’ll only sing public-domain songs on the air, is a funny one, but the main focus here is the escalation of what Natalie calls “the Casey situation” (“It’s not a situation,” Dana objects, to which Natalie replies, “I’ve already named it!”). Of note is the delicate writing and acting of Dana and Casey’s conversation about her upcoming ski weekend with Gordon; it slowly slowly ramps up from idle, strained chatter between friends to a real confrontation, and the way Huffman barks “KNOCK IT OFF” at the end of that escalation, and means it, makes clear that this is not just some cute Ross-and-Rachel, will-they-or-won’t-they thing.
35. “The Sword of Orion” (Season 1, Episode 18)
One of the things that becomes clear, when binge-watching Sports Night, is a noticeable increase in the pacing during the first season, a screwball snap that came to define the series but wasn’t quite there until around episode 15 or 16. The hyper-stylization of the dialogue, from above-TV-average to Sorkinese, takes over at roughly the same rate. So by this late-season episode, they’re really firing on all cylinders – particularly in the duet scenes between Josh Charles and Teri Polo (later of Meet the Parents) as Rebecca, the new object of his affection; the way they bat their jazzy dialogue back and forth is a joy to watch. The central metaphor of the Jeremy story, in which he becomes obsessed with a yacht wreck in order not to think about his parents’ divorce, is more than a little cumbersome (“I’m not sure how this boat that was supposed to win met with this kind of disaster”), but in general, “Orion” is quite an adroit dramatization of how we will force ourselves to become distracted by the stupidest bullshit in order to avoid thinking how our lives are falling apart.
34. “Ordinance Tactics” (Season 1, Episode 20)
Viewed from this vantage point, there’s a slight pall cast over this particular episode, as it concerns a bomb threat in the building where our characters work and broadcast; a building that is, as we’ve seen in countless establishing shots, the World Trade Center. (The show ended its run in spring of 2000; I’ve often wondered what its 9/11 show would’ve even been.) Aside from that, the most memorable element of “Ordinance Tactics” is Natalie’s good-natured refusal to acknowledge the “temporary” breakup Jeremy has proposed; her refusals (“It won’t take”), pronouncements (“I’m taking you into receivership, we’re not broken up”), and pre-show announcements (“I’m his girlfriend and he’s seen me naked many, many times”) are the closest the show’s come to Seinfeld territory, which is intended as a compliment. Also nice is Sally’s terse response to a dig from Casey — “Y’know, for someone I’m sleeping with, sometimes you don’t say the nicest things to me” — a real moment of humanity for a character it’s easy to view mostly as a plot convenience.
33. “Special Powers” (Season 2, Episode 1)
This one should probably rank higher simply as recognition for one key breakthrough: At long last, in season two, the laugh track is gone altogether. (They’ve also got new, overdue sets for Dana’s office and Anthony’s, the neighborhood bar). Sorkin also constructs a clever method for covering the summer break: He opens with a montage, ticking off how many days have passed since Dana and Gordon’s breakup, which Casey is presumably using as a guide for making his move. (That montage also gives us time to enjoy, dialogue free, how much better everyone’s hair is this season.) The title comes from the Jeremy/Natalie subplot, which isn’t one of their best — it’s yet another opportunity for Jeremy to be the mature, intellectual one. But Dana going for it is sexy and wonderful, informing Casey that the “statute of limitations” he’s been waiting out is not the 90 days he thought it was, with this great line: “It’s 60 days. What you been waitin’ on, McCall?” Between their first-kiss scene and Natalie’s promises for her and Jeremy’s make-up sex, this may not be Sports Night’s best episode, but it’s certainly its horniest.
32. “The Sweet Smell of Air” (Season 2, Episode 12)
William H. Macy’s Sam Donovan is back after a brief disappearance, and the way he lays back and lets Dana lose her shit all on her own is genuinely funny. But the big news here is, perhaps inevitably, the subtle pivoting of Sam from a sparring partner to romantic possibility for Dana — a move that wisely takes advantage of the married co-stars’ considerable chemistry. Also of note: A rare season-two appearance by Sally, who tries to schmooze Sam (it goes about as well as expected), and Natalie sitting in for upcoming guest Michael Jordan in a practice interview.
31. “Kafelnikov” (Season 2, Episode 5)
The West Wing premiered concurrently with Sports Night’s second season, which meant Sorkin’s focus was split – and thus we have the first episode of the show with no Sorkin writing credit. Matt Tarses and Bill Wrubel, long-timers on the show, handle it well; you honestly don’t feel Sorkin’s absence, so established is the show’s style (and his). The treat here is the test show for the Y2K changeover, a comic masterstroke filled with hilariously goofy improvisations and, clearly, genuine laughter from the crew of the show outside the show. But the Y2K business doesn’t just get them easy laughs (or easy earmarking as a late-‘90s series); in the conversation at the episode’s close, about whether to dread or anticipate the future and its technology, we can see the broad strokes of Sorkin’s screenplay for The Social Network.
30-29. “Kyle Whitaker’s Got Two Sacks” / “The Reunion” (Season 2, Episodes 7–8)
Here’s a fun fact: During Sports Night’s run, ABC was headed up by Jamie Tarses (whom Sorkin would later use as the basis of Amanda Peet’s character on Studio 60). And her brother, Matt Tarses, was a writer and co-producer during both seasons, so I wonder what he thought of the B-plot in this episode, which concerns the show having to employ the wildly incompetent relative of a network executive? At any rate, it’s a juicy thread, not just for the shade potential, but the complication of the Natalie-Jeremy dynamic: She wants the guy fired, Jeremy wants to give him another chance, and we get a rare taste of the potential friction caused by simultaneously navigating a personal and professional relationship (and, it is noted, a relationship where she is his superior). Meanwhile, Dan’s therapy scenes start getting intense – this is straight-up psychological drama, seeming to point the way towards Charles’ later gig on In Treatment.
In “Two Sacks,” the tee-up and reveal of Dana’s brother’s name on a list of players implicated in a steroid scandal is an effective piece of narrative construction; Huffman handles the arc of these episodes gracefully, going from shock to rage to finally stopping herself while chewing him out, looking at him, and noting, “You look tired,” and then they just talk to each other. It’s lovely.
28-27. “Mary Pat Shelby” / “The Head Coach, Dinner and the Morning Mail” (Season 1, Episodes 5–6)
Another two-part episode takes on the issue of women in the locker room, as Natalie’s preshow interview of a football star results in sexual-assault charges. And it’s an episode full of thorny issues for journalists: before the locker-room assault, Dana has already agreed that the player’s domestic violence charges are off-limits, and later realizes, and confesses, that she chose Natalie for the pre-interview to get a reaction out of the guy. “Does she know that I sold her out?” Dana asks, and it’s a tough question. The second half gets into equally challenging territory; Natalie’s colleagues are letting on-the-job errors slide, to her chagrin. “Why aren’t you laughing at me?” she asks them. “Why aren’t you mad at me?” It’s a good beat, getting at how sensitivity doesn’t necessarily mean treating someone differently. And, as a side note to all of that, the second episode features an all-time great Dana/Casey exchange: “How am I conversationally anal retentive?” “Let me answer that question in four parts with the fourth part first and the third part last. The second part has five syllables—” “All right, all right, all right!”
26. “The Apology” (Season 2, Episode 2)
Sorkin was nominated for an Emmy – his only nod for the series – for the writing of this episode, in which Casey is asked to apologize on-air for voicing his support of marijuana legalization, and takes the opportunity to tell the story of how he lost his brother to drugs. That big Sorkin barn-burner of a stagey monologue is, indeed, effective – but the most devastating moment comes a bit earlier, when Dan makes a Rosa Parks reference in front of Isaac and the network execs, and Isaac waits until the suits leave to take his anchor down a notch: “Danny, you know I love you, don’t you? And I because I love you, I can say this: No rich young white guy has ever gotten anywhere with me by comparing himself to Rosa Parks.” The show was obviously still trying to hit its stride here (it even includes the old “he’s standing right behind you” gag), but in those two moments, viewers got a look at how the series could both puff its chest, and do better.
25. “Shane” (Season 2, Episode 6)
The “previously on Sports Night” opening calls back to “The Apology,” from a full season earlier, which gives you an idea of how deep this therapy arc is diving into Dan’s psychosis. And Josh Charles benefits; the scenes of Dan fumbling a teaser audio recording comprise some of his best acting in the series, capturing the panic and fear of realizing (and/or admitting) you don’t have it together. It’s easy to read the frequent storylines about ratings struggles and network interference as Sports Night getting meta, but when Abby the therapist tells Dam he’s gonna be fine and he replies, “Doesn’t feel that way,” it’s clear we’re getting into some very personal territory here.
24. “The Cut Man Cometh” (Season 2, Episode 11)
Two of the best character actors of the ‘70s and ‘80s - Allen Garfield and Peter Riegert – give this Emmy-winning episode its bounce. The latter shows up as Dan’s father, much discussed in therapy, whose general shittiness (“Shouldn’t wear your hair so short, makes you look a little bit gay”) explains much about why Dan needs therapy. The former is a gem as the hilariously terrible color man at a big boxing fight; he can’t keep Dan and Casey straight and contributes such invaluable commentary as, “When it comes to the sweet science, I’m not much on predictions. But I will say this: one of these men is gonna win this fight, and the other will most surely lose.” Most importantly, this episode all but confirms the end of the Casey/Dana situation with her apology for the ridiculous dating plan. And then they head off to try and fill the remaining 88 minutes of airtime after the seven-second fight.
23. “Ten Wickets” (Season 1, Episode 21)
By this point in season one, they’re using the laugh track so sparingly that it sort of startles you when it appears, even after a good line like Dana’s, “There are three things I’m doing: I’m losing things, I’m forgetting things, and … there’s a third thing.” And some big laughs are wrung out of the crew’s inability to wrap their heads around anything having to do with cricket. But the strength of “Ten Wickets”’ is its dramatic plot: the breakup of Dan and Rebecca, who has decided to go back to her husband. What Sorkin’s script gets right is the way that you can so often see a split like this coming, and attempt to sunshine it right out of your head, with good cheer and gifts — but Dan knows the second she looks at him, and he reads her like a book with a simple, “Uh oh.” It’s a great, true, human moment.
22. “Small Town” (Season 1, Episode 13)
Sabrina Lloyd really gets to shine in this episode, which dramatizes her first time running the show solo — and crushing it. She hangs up on Dana’s concerned control-room call, shuts down Jeremy and even Isaac when necessary (“You’re good,” he tells her after, recalling the “I had no idea she was this good” bit in Broadcast News, the influence of which is all over this show). “What’d you think I was around here Jeremy, just some gal Friday?” she asks, and there’s real edge in that question. (Lloyd, for the record, should have been a huge star after this show ended.) We also have the first of two appearances by Lisa Edelstein, who turned up in several first-season episodes of West Wing; her character turns out to be a bit of a bait-and-switch, but more on that later.
21. “Louise Revisited” (Season 2, Episode 4)
Don’t worry — title notwithstanding, this is not another “Dear Louise” episode, but merely a reference to Natalie’s new pen pal. The main focus here is Dana’s dull dinner with a high-school classmate, which prompts her spontaneous decision to take off her panties at dinner, leading to the most perfectly timed beat in Sabrina Lloyd’s run on the show — which is saying something. Mostly, however, “Louise Revisited” highlights the value of the Sam Donovan character for puncturing the characters (and, by extension, the occasional self-importance of the show); throughout his episodes, he’s entertainingly disinterested in their nonsense, and when he says here, “I’ve noticed you people have an ability to chatter at someone with energy and enthusiasm, regardless of whether they appear interested or not,” well, it sums the show up pretty nicely.
20. “Thespis” (Season 1, Episode 8)
Here we have Sports Night’s version of a bottle episode — one that’s limited to the execution of a single, gaffe-prone show-within-the-show (the top half-hour, specifically — so it’s basically done in real time). The on-air fumbles and goofs are funny, but the serious beats are what stick. Guillaume is all heart (and dignity) in this moment of genuine fear; witness the moment he gets to himself when Dana tells him that her sister-in-law lost the baby in a similar situation. He’s not a greedy actor, so he doesn’t make a meal of that moment. But he takes it. Also, in shades of late season two, we get our first hint at the complications buried beneath the cool-buddy surface of Dan and Casey’s relationship; Dan is clearly hurt by Casey’s forgetfulness (and the way she immediately tries to feminize Dan in response is telling). But this mini-conflict also wraps itself up well; Dan’s handling of it is especially genuine and heartfelt. Also, this episode includes a wet turkey falling from a light grid, so it’s clearly top-20 material.
19. “The Six Southern Gentlemen of Tennessee” (Season 1, Episode 11)
There are some real problems with this one: Casey’s guest spot on The View (on ABC!) is an awfully clumsy piece of corporate synergy, a pre–West Wing Janel Moloney gives Casey a good and totally unrealistic speech, and Jeremy dismisses the women’s ice-hockey team for “beating a bunch of Slovakian cocktail waitresses,” a really unfortunate bit of casual sexism. Yet all of those moments are overpowered by the A-plot, in which Isaac must decide what to do about a feature on “the Southern tradition” in response to a Confederate flag controversy. It gets into some thankfully candid material about when to pick one’s fights and why (Isaac tells Dan, sternly, “You gotta stop thinking of me as the champion of all things black”), and it culminates with one of the finest monologues Sorkin has ever written. “In the history of the South, there’s much to celebrate,” Isaac notes, in his on-camera editorial, “and that flag is a desecration of all of it. It’s a banner of hatred and separatism.” In a scene like this, you can see the seeds of the kind of self-importance that came to full flower in the lesser moments of The Newsroom, but that doesn’t diminish the episode’s still-relevant power.
18. “Dana Get Your Gun” (Season 2, Episode 13)
The entire opening sequence — tracking the very funny process of deal-brokering and politicking, trading one favor for another for another, in order for Dan to get a night off — is a little gem of comic ingenuity, and the awkwardness of co-host Steve Sarris’s on-air meltdown yields some solid, Office-style laughs. But the greatness of “Dana Get Your Gun” lies in the duets between Huffman and Macy; it’s basically about eschewing simple left-wing talking points, with Sam’s simple but effective assurance that, “The world isn’t really like that, Dana. It’s a lot more interesting than that.” And then there’s the masterful build to Natalie and Jeremy’s unexpected (second) breakup, which begins as good-natured but then gives way to all-out ugliness. “Before we go on, do you wanna make any more trashy accusations about me?” Natalie asks, and Jeremy is happy to comply: “There are things about you I find unattractive. There are things about you I don’t like.” And like that, they’re done; the last shot of the episode, from behind with no music as they take their seats on either side of Dana in the control room, is quietly devastating.
17. “Rebecca” (Season 1, Episode 14)
One of the best things about Sports Night is the many ways its writers concoct to have their characters tell each other they’re tired of listening. This one has Isaac ask Casey, “How many more questions do I have in my future?”; it also includes a dialogue scene where Dan grows impatient with Casey’s interruptions to his story and replies thus: “You don’t have to ask questions, I’m gonna tell the story clearly. The things you need to know, I’m gonna tell you.” At any rate, Dan’s attempts to connect with Rebecca — whom he thought liked him, and discovers doesn’t even remember him — are very painful and very funny, and Isaac’s dressing-down of slimy network exec J.J. is one of Guillaume’s very best moments on the series.
16. “Dana and the Deep Blue Sea” (Season 1, Episode 15)
A fair amount of Sports Night’s gender politics haven’t aged particularly well, which isn’t surprising, and Dan’s good-natured refusal to take no for an answer with Rebecca ranks pretty high on that list. But he does, at last, discover the source of her hesitation: She was once married to a sportscaster, and one that treated her quite poorly. Dan has a response: “The fact that you’d think that man’s low-grade brand of manhood is any way indicative of my profession is beneath your obvious intelligence and class.” It’s a good line, and also a very written line — and an underrated thing about this show is Josh Charles’s ability to sell stylized dialogue as naturalistic. And thus the scene that follows — when she barely, carefully lets him in by acknowledging she saw him make a particularly silly onscreen gaffe — is lovely, and dizzyingly well-acted by Charles and Polo.
15. “April Is the Cruelest Month” (Season 2, Episode 19)
One of the most striking things about this late season-two episode is how thoroughly the Casey/Dana thing really seems to be over; the “dating plan” and its subsequent failure seemed to be a fairly standard sitcom romance-avoidance device, but had the show continued, it seems like they would have had trouble bringing that back. That aside, the focus here is the news that, per CSC’s CEO, “Finance is going to be playing a more hands-on role in CSC operations,” to which Isaac properly responds, “Well, that’s good news!” Coming so close to the cancellation of Sports Night (the ABC show), these episodes about the financial and ratings woes of Sports Night (the CSC show) feel very much like Sorkin & Co. working out their frustrations on the page, which makes for some sharp, passionate episodes. It’s a fascinating meta-textual thing: a show that’s about to end, doing shows about a show that’s about to end. Other pluses: Natalie’s priceless response to finding out Jenny’s real job, and the chasteness of Jeremy’s relationship with her (“You dated a porn star and never slept with her? What a goober”); Dan and Casey hugging it out and making up; and the dramatization of a seder ceremony, right there on network television, where such explicitly Jewish matters are usually implicit at best.
14. “Cliff Gardner” (Season 2, Episode 3)
Network struggles are fueling this top-shelf episode from earlier in the second season; the gist of the network notes, that the writing on the show-within-the-show is too smart for a mass audience, feels like Sorkin working through some stuff. We see Dana really unraveling — feeling the pressure of the job in a way we haven’t seen before — and how the network’s meddling and Sam’s mind games are turning them against each other, which is a fairly astute observation of how these things usually go. And it feels like there’s something of a fantasy mic-drop/wishful-thinking element to how Sam closes the network notes meeting — the ultimate Sorkin walk-and-talk, really, a wordy monologue that ends with a parting shot and shoving the dunderheaded execs right out the door. The monologue’s subject, television inventor Philo Farnsworth, is clearly near and dear to the author; he was also the focus of Sorkin’s sharp 2007 Broadway play The Farnsworth Invention.
13. “And the Crowd Goes Wild” (Season 2, Episode 14)
The Sam and Dana simmer finally comes to a boil as he’s heading out the door on his last day — he makes a big speech about not making any attachments, right before he and Dana make out. In other words, there’s a lot of deft two-things-can-be-true-at-once writing and acting happening in this episode; the other strand concerns how Natalie is desperately trying to play off the Jeremy breakup like it’s no big deal, before falling apart in the guise of not turning over some footage to the NYPD. “I’m supposed to hand over these things, I’m supposed to hand over these things that are ours,” she protests, and it’s clearly not about those tapes at all; there’s such warmth and humanity in the scene of her crumbling in Isaac’s office. It’s a good arc, and Lloyd acts the hell out of it. But the pathos of that scene is just preparation for the closing images, in which the camera moves in on the control-room monitor of the show in progress — and then just past it, to Sam slipping away forever, with just a dash of regret on his face.
12. “Celebrities” (Season 2, Episode 15)
It’s a shame Sorkin hasn’t written a proper romantic comedy since The American President, because the scenes of potential partners first meeting and sparking are so often memorable (Mary-Louise Parker’s first scene with Bradley Whitford on The West Wing also comes to mind). So the sparkling back-and-forth between Jeremy and Jenny (the wonderful Paula Marshall) is the highlight of “Celebrities,” though certainly not its only virtue; right from the jump, the episode gets at the very relatable difficulty of losing friends in a breakup. But the Jeremy-Jenny scenes are next level — it’s like a great little one-act play, her A+ flirting and his flustered flattery, all coming to a head when Jeremy realizes why she looks so familiar to him. “Anyway, I’ve got a website,” she tells him, “so if you’ve got a credit card you can look at me where it’s more comfortable.”
11-10. “Draft Day: Part I — It Can’t Rain at Indian Wells” / “Draft Day: Part II — The Fall of Ryan O’Brian” (Season 2, Episodes 17–18)
Sorkin’s always loved a good multi-parter; he did two-parters on The West Wing and The Newsroom, and even a three-parter on Studio 60. This was the only explicitly branded two-part episode of Sports Night, and it’s constructed like one — Matt Tarses and Sorkin’s teleplay for part one treats it like a genuine cliffhanger, meticulously setting up all the negative outcomes for everyone if it rains at Indian Wells, and then ends by letting us know those outcomes are all happening, see you next week. The Jeremy-Jenny story here sort of peters out, unfortunately. The Dan and Casey conflict, however, is rich and sticky. We’ve grown to like them and value their camaraderie so much that seeing them hitting each other in what are clearly long-festering sore spots (the magazine ranking, their comparative paychecks, etc.) is legitimately hard to watch.
9. “Bells and a Siren” (Season 2, Episode 20)
It’s so much fun to get away from all the woes of the world by binging this 20-year-old dramedy, surely nothing here to remind us of the current madness and goddamnit here’s a whole bit about Trump and his ex-wives. (“She was really good in Will Rogers Follies!”) At any rate, this is another late-series episode where the anxiety happening behind the scenes is palpable onscreen — people are starting to talk about other jobs, prepare their goodbyes, and even burn some bridges (there are not one but two jokes at the expense of Felicity, Imagine Television’s other, longer-running 1998 series). It ranks this high for three reasons: the way every single person’s attempts to insult Natalie and crumble her confidence before an SNL job interview translates as genuine love and affection (Dana: “Is that what you’re wearing?” Natalie: “I hate you!”); the highly personal material that finds Isaac, and thus Guillaume, wrestling with the physical effects of his stroke; and the perfectly executed payoff to the carefully prepared “bells and a siren” joke.
8. “Napoleon’s Battle Plan” (Season 1, Episode 22)
This late first-season episode crafts a similarly expert setup and payoff: the idea that Casey will execute Napoleon’s battle plan (showing up and seeing what happens) to keep the Gordon-Dana union from happening. Dan, of course, knows that’s not going to work, and watching him strategically work his way up to spilling the secret about Gordon’s cheating to Natalie is uproarious. More importantly, the acting Huffman is doing in this episode is admirably complex — she transcends the inherent soapiness of this love triangle and, in her reactions to these bombshells, reveals much to us, and to Gordon, about what really matters. And in the end, Casey was right. “Look. It’s your plan,” Dan notes, and his partner agrees: “I just showed up. Now, we’ll see what happens.”
7. “La Forza del Destino” (Season 2, Episode 21)
This was the first of two second-season episodes directed by Timothy Busfield, as he was simultaneously guest-starring as journalist (and occasional C.J. Cregg love interest) Danny Concannon on The West Wing; later, he would appear as, wouldn’t ya know, a director on Studio 60. Offscreen woes continue to seep onto the screen; Dana scolds her cast, “We are on life support now! We are way past the ‘show business is funny’ stage.” But the highlight here is the first appearance of Agent Coulson himself, Clark Gregg, as a mysterious bar-dweller who seems to know an awful lot about the show’s prospects, which he parcels out carefully to Dana. Like Macy, Huffman went way back with Gregg (they all started out at the Atlantic Theater Company), and they’re magnificent together, flexing the kind of well-honed timing that still rarely makes its way to network TV.
6. “What Kind of Day Has It Been?” (Season 1, Episode 23)
For whatever reason, Sorkin adores this title; he used it not only for this, the first season finale of Sports Night, but the first season finales of The West Wing and Studio 60, and the series finale of The Newsroom. And this episode features perhaps the finest acting of the series from both Peter Krause and Felicity Huffman. His comes at the culmination of his subplot with his son, after Casey discovers that the kid’s been padding his Little League stats to make his old man proud — a heartbreaking moment that Krause ends up handling with grace. “Pay attention,” he tells his son. “In your lifetime, you will never embarrass me. It’s not gonna happen.” It’s just a lovely scene (even if the plinky music is too, too much). Huffman’s comes not in words, but gestures — an incredible walk-and-not-talk, where she has to get through the newsroom, ahead of Gordon, who is about to break up with her for good. She says nothing; she just toys with her hands and puzzles it through on her face, and keeps answering questions from the staff on the way, because the job doesn’t stop. With all that and Guillaume’s gooseflesh-raising return to the show, this is an all-timer of an episode.
5. “Quo Vadimus” (Season 2, Episode 22)
There’s plenty of melancholy and paranoia to go around, at least early on, in the series finale; plans are being made, goodbyes are being said, and reunions are at hand (look, it’s Teri Polo, now known as the co-star of Meet the Parents!). So there’s something genuinely thrilling about the way Sorkin’s script reveals who exactly Clark Gregg is, and how he’s going to rescue them; the breathlessness of his scene with Huffman back at the bar, and the off-handedness of his admission (“Turns out I picked up a few more shares of stock, yeah”) is electrifying. But best of all is his summation of their chances of survival, one of the all-time great television subtweets/parting shots: “It’s a good show, Dana. Anybody who can’t make money off Sports Night should get out of the moneymaking business.” (Recall, also, that when Sorkin was fired from The West Wing, his last episode before turning it over to producer John Wells involved a literal transfer of power.) And thus, with Sports Night rescued at the 11th hour by a wise soul who saw its potential, we get a big ending with our beloved anchors and crew exchanging lingo and shop talk. It was all wishful thinking, sure, but a nice thought nonetheless.
4. “Smoky” (Season 1, Episode 12)
One of the best running bits on Sports Night is the utter inability of everyone involved in the show, from Dana on down, to keep anything to themselves. (It even gets mentioned at the end of the last episode: “My scouting says you don’t keep a secret so good.”) So Isaac’s plan to groom Dana to take over if/when he gets tossed (he’s nervous after the Confederate flag editorial) ends up rippling through the entire staff, and his attempt to get to the bottom of the leak results in this, the greatest dialogue exchange in the entire series:
Isaac: Things that I say in my office stay in my office.
Dana: Natalie’s my second-in-command, she’s the only one I told.
Natalie: Jeremy’s my boyfriend, he’s the only one I told.
Jeremy: I told many, many people.
If “Smoky” just had that, it’d be top-five material — but it also has one of the great Dana-Casey scenes, in which she dares him to “flirt with me now” to practice getting back out there. (Her prompt is telling: “Tell me why you like me better than Sally.”) It’s just a fun scene, sexy and playful and genuine — a nice hint of what a real Casey and Dana relationship might’ve looked like, were it not for the stupid dating plan.
3. “The Local Weather” (Season 2, Episode 16)
One of Sorkin’s trademarks is the cleverly constructed flashback structure, with a character telling the story in a somewhat formal setting, prompting scenes of the events in question. He uses it in The Social Network, the “Bartlet for America” episode of The West Wing, and as the framework for the entire second season of The Newsroom. But the only time he used it for Sports Night was here — and it’s an experiment so successful, it’s easy to see why he brought it back. Dan spends his entire non-appointment with Abby standing in the doorway with his coat and scarf on, explaining the psychological intensity of Jeremy’s promising rebound and the emotional exhaustion of watching a long-jump record that stands for like a minute and a half. Dwell too long on things like that, and everything can start to feel pretty pointless, and that’s not the kind of theme we were used to extrapolating from network comedies in the ‘90s.
2. “Sally” (Season 1, Episode 16)
Sports Night is usually paced within an inch of its life, so the contrast of this episode’s opening — the languid, laid-back semi-despair of a slow news day — is striking. There’s a wonderful idle hands/devil’s playground vibe to this entire episode, as confessions are spilled and mistakes are made while sitting around waiting for the games to start: Jeremy contemplates the inconsistencies of the Bible (an idea that would recur, with some frequency, on The West Wing); Natalie tries to keep Dana from sounding nutty with Gordon; Dan tries to figure out who Casey slept with; and then Sally shows up and reveals that it was her. All that dithering around ends up diverting us from the big reveal sitting right there, the shocking revelation of exactly where Casey’s missing shirt went after his hook-up with Sally:
Gordon: What’s on your mind, Casey?
Casey: You’re wearing my shirt, Gordon.
Gordon: I was wondering why it felt so tight.
I still remember, no exaggeration, leaping out of my chair during this exchange — it was, for me, the moment Sports Night went from a good show to a great one. And the “Crimson and Clover” pull-away and play-out is awfully good too.
1. “Eli’s Coming” (Season 1, Episode 19)
“You’re gonna have quite a little day, ” Casey tells Dan, and he doesn’t know the half of it; they’ve got a perfect storm of catastrophes on deck for March Madness coverage. The turn on the Bobbie Bernstein story is excellent, making the hero (Dan) into a villain (albeit briefly); the fighting between Dana and Casey is loaded and rough-edged (“Dana, whatever we’re gonna do, can we not do it in front of the help” is an ugly line, and to his credit, Krause doesn’t soft-soap it); and the health scare for Isaac was especially potent for those of us who watched the show when it first aired, wondering if the actor’s stroke would make its way into the show, unsure if the actor would, in fact, ever return. “This day’s got the earmarks, Casey,” Dan says. “Rebecca isn’t here, Isaac isn’t here. There’s a strangeness about this day.”
And then he puts it into words: “Eli’s coming,” the title of a Three Dog Night song that’s not, in fact, about a dark cloud of events, but about an inveterate womanizer — but the words are so evocative, and the connotations of it are so vivid, that when everything does go to pieces and the needle-drop sneaks onto the soundtrack at the end of the episode, we know exactly what Danny meant.