The West Wing 20th Anniversary

Top 25 Best Episodes

Episodes 5-1

September 22, 2019

Premiering on September 22, 1999, this Fall will mark the 20th Anniversary of Aaron’s Sorkin’s seminal political drama, The West Wing. Telling the story of fictional President, Josiah Bartlet, and the trials and tribulations of his senior staff, The West Wing helped to usher in the Golden age of serialized drama that we’re still living in today. It is not hyperbole to say, The West Wing changed television in a real way, and for the better. In the end, The West Wing is a love letter to civil servants who sacrifice so much for their idealism and the greater good.

This Top 25 List represents the second in a series of articles I will be writing over the coming months, celebrating the show’s 20th Anniversary. Read my first entry here, the Best Seasons of The West Wing. Due to the size of these articles, I’ll be publishing the Top 25 List in 5 Episode Installments. This is Part 4.

Over the course of 7 Seasons, The West Wing aired 156 episodes, but really, 154 episodes. Two, “Documentary Special” from Season 3 and “Isaac and Ishmael,” a standalone episode produced and aired within 3 weeks of the terrorist attacks of September 11, 2001, were non-canonical “special” episodes. Over the course of the first 4 seasons, when Aaron Sorkin directly ran the show and wrote almost all of the episodes, week after week saw groundbreaking television; complex characters telling (mostly) nuanced stories about the successes and failures of government and those who run it. After Sorkin left in Season 5, there was a noticeable shift in tone and decline in quality, but the show recovered, and, in the end, aired a very good final Season 7 (my fourth favorite season of the show).

Below, I rank my Top 25 Episodes culled from the 7 Seasons of the show. These episodes represent, to me, the greatest parts of what The West Wing could be when it was at its best.

This is the fifth installment of the Top 25 List, covering Episodes Ranked 5-1. You can read about all of our West Wing 20th Anniversary Coverage Here!

The Top 25 Episodes of The West Wing:

5. “17 People” (Season 2, Episode 18).

“17 People,” by revealing President Bartlet’s MS to Toby, begins the Season 2 endgame. Like so many of Season 2 and 3’s best moments, Toby and Jed go at each other with pure emotion of unbridled anger and disappointment. From the beginning moments of the episode, punctuated by the thump thump of Toby’s rubber ball, “17 People” is an hour of tense television; the kind of TV where you have to remind yourself to breath.

Watching Toby work through the ramifications of Jed’s disclosure combined with the ramping up of his anger at Bartlet’s deceit, matched blow for blow by President Bartlet’s increasing anger at the vitriol being thrown at him; even now, two decades later, this episode makes me hold my breath.

This episode features Schiff and Sheen at the Top of their craft, a roller coaster ride of emotion – loud verbal explosions followed by unbearable silences where only the sound of a ticking Grandfather Clock can be heard. It’s a masterclass in writing and acting, a stand out for anyone trying to point at what great television is.

“For 90 Minutes, there was a coup d’état in this country.”

*Silence except the ticking grandfather clock*

“And the walls came tumbling down.”

4. “In the Shadow of Two Gunmen” (Parts 1&2) (Season 2, Episodes 1&2).

I have watched the two hour season premiere of Season 2, “In the Shadow of Two Gunmen,” more than any other episode of The West Wing. I’ve seen it no less than 50 times.

Sorkin found himself coming into Season 2 with an unexpected hit on his hands and had two missions with this season premiere: complete the Rosslyn shooting storyline begun by the Season 1 cliffhanger and more importantly, reintroduce the show to newer viewers and give us the first of many glimpses into the origin stories of these heroes of public service.

In the present, we are dealing with the revelation that not only was President Bartlet shot (non threateningly) but also, Josh. The end of the cold open where Toby finds Josh holding his stomach as blood seeps out of him, it still makes me teary — and I have seen this 50+ times. Everyone is at the top of their game in this episode as we watch them deal with the fall out of the shooting but, for me, it’s the flashbacks that make this one of the top episodes of The West Wing ever.

Through Josh slipping into a coma-like state, we are brought back two years to the infancy of the Bartlet campaign. We see how Leo recruited Josh to come board (and eventually the other main staffers) and how Toby, already on board, is almost out the door. It’s this moment below, however, that seals the deal for me on The West Wing.

Watching the conversation between Jed and Leo, two old friends, discuss why Leo wants Jed to make it to the White House, you can’t help but drink the Kool-Aid and fall in love with these people. Whether you agree with their politics is immaterial, their devotion to a cause, to the idea of serving for service sake, it’s inspiring and one of the best examples of the love letter that The West Wing was to public service.

“This is the time of Jed Bartlet, old friend. You’re going to open your mouth and lift houses off the ground. Whole houses, clear off the ground.”

3. “Bartlet for America” (Season 3, Episode 10).

Another flashback episode, “Bartlet for America” features Leo’s retelling of how he initially convinced Jed to run for President and also, filled in more of the nascent campaign that we began to explore in “In the Shadow of Two Gunmen.” The plot for the episode is that Leo has been called before a congressional panel to testify on what he and others in the administration may have known about President Bartlet’s MS diagnosis prior to it becoming public.

“Bartlet for America” is a prime example of Sorkin at the height of his story telling powers. Seamlessly shifting us back and forth in time while never confusing us as to where we are or why we’re watching something, BFA is pure beef, no fat on this storytelling burger, an Aaron Sorkin classic. John Spencer was a gifted actor who shined brightly in The West Wing but, for me, when I think of his best moments over the course of the series, really his entire career – it is “Bartlet for America” that I come back to over and over.

The scene I am using is another one of those that never fails to make me get misty eyed.

“Merry Christmas Leo … that was awfully nice of you.”

Then Leo breaks down in tears, God, I can’t even.

2. “Noël” (Season 2, Episode 10).

After “Midterms,” our show and characters largely returned to normal life; the wounds of Rosslyn left to heal internally. That is, until we get to the Season 2 Christmas episode, “Noël.” Through another flashback episode, this one only going a few weeks back, we examine Josh falling further and further into the throws of PTSD.

After a uncharacteristic blow up in the Oval Office and other troubling events, Leo has Josh sit down with a no nonsense trauma specialist, Dr. Stanley Keyworth (Adam Arkin in the first of several recurring appearances on the show). Josh and Stanley trade barbs the entire episode as Josh reluctantly relays the events of the past few weeks and days to the good doctor. Stanley is trying to get Josh to come clean about what’s really happening inside his head and how he hurt his hand (which we see is bandaged). The episode culminates in an increasingly agitated Josh telling the Doc (and us) that he punched his hand through a window.

If “In Excelsis Deo” was the episode where we get to see inside Toby’s hard shell, “Noël” is the episode where we get to see how much emotional pain Josh is in following being shot at Rosslyn. It becomes a part of the character’s pathos and Bradley Whitford solidifies his role has one of the most impressive actors on the entire show. Seriously, Whitford takes us through ALL of the emotions in “Noël” and it’s a singular performance that is hard to beat across any television show ever.

For our scene, I have chosen the episode’s climax, with a diegetic Yo-Yo Ma cello performance serving as the background score. It’s so powerful, even without any other context.

1. “Two Cathedrals” (Season 2, Episode 22).

I don’t this will come as a terribly controversial choice, even if it’s not your Number One favorite episode of The West Wing, I bet all the money in my pockets against all the money in your pockets (a “17 People” shoutout) that it’s in your Top 5 or 10.

Following the shocking death of Mrs. Landingham at the end of “18th and Potomac,” the Season 2 finale of The West Wing, “Two Cathedrals” has President Bartlet burying his longtime friend and confidante while also preparing to confess his MS diagnosis to the country in a televised interview. There are a couple of things on the President’s mind as “Two Cathedrals” unfolds.

Like the previous 3 entries in this Top 5, “Two Cathedrals” is a flashback episode. But, unlike the workplace -based flashbacks we’ve seen already, “Two Cathedrals” takes us on a very personal journey, bouncing us between the present where a thoroughly numb Jed goes through the motions of this stressful day and the long ago past when Jed first met and befriended a young Dolores Landingham (played wonderfully by Kirsten Nelson). Young Jed (played Jason Widener with pitch perfect devotion to Martin Sheen’s idiosyncrasies) and Young Dolores meet when she takes over as Jed’s father’s executive assistant at Jed’s expensive private school (where Mr. Bartlet is the headmaster).

Not only does “Two Cathedrals” teach us all about the origin of this longtime friendship that we’ve just always taken for granted but it plants the seeds of conflict which will erupt in Season 3 as the President’s toxic relationship with his father (who was a real douchebag) affects his re-election campaign. Oh, speaking of, “Two Cathedrals” also ramps us up for the next season by dangling the question of whether President Bartlet will run for another term (in direct contravention of his agreement with Abby).

Jed only appears to be truly awake twice in this episode, at the end when he bounds into the press conference, full of renewed purpose, to take on the question of re-election and this scene below, where is bubbling anger finally bubbles over in a Latin-filled rager against God … while smoking in the National Cathedral. It’s an epic scene, maybe one of the most famous from all 7 seasons of The West Wing and proves why “Two Cathedrals” is our Number 1 Episode of The West Wing of all time!

(this clip provides a Latin translation at the bottom so, you’re welcome)