The West Wing 20th Anniversary: The Top 25 Best Episodes (25-21)

The West Wing 20th Anniversary
Top 25 Best Episodes
Episodes 25-21
June 24, 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 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 List in 5 Episode Installments.


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. I think most people will agree that my Top 5 represent the best, though everyone’s order may differ.  Slots 6-25 represent to me, either in part or in whole, the greatest parts of what The West Wing could be when it was at its best. This first installment will tackle the Episodes Ranked 25-21.

The Top 25 Episodes of The West Wing:

25. “Shutdown” (Season 5, Episode 8).  

With Jed and his family still trying to recover from the horror of Zoey’s kidnapping, he’s still pretty out of it by the time we get to “Separation of Powers” (Episode 7 of Season 5). At the end of that episode, President Bartlet finally remembers he’s got a duty and job to do and also, Speaker Haffley is a giant dickweed and he walks away from the Budget negotiations with the Republicans. shutting down the Federal government. The episode (in)famously ends on the Law & Order-inspired clink clank clunk. A low point for this show.

But, the following episode, “Shutdown,” gives The West Wing a good dose of old school TWW problem solving. When Abbey returns to the White House and asks her husband why Josh is being treated like a little bitch by Leo and Angela Blake, Josh gets taken off the bench and is put back in the game (enjoy it while you can, fair treatment of Josh won’t continue). Jed and Josh work together to upstage the Republicans. They literally march up to the Hill to confront the Speaker and his cronies. Haffley overplays his hand (naturally, remember, he’s a dickweed) and the President is able to negotiate a final budget that’s a good compromise, if not exactly what he wanted. It’s a return to the “we can do this if we work together and act creatively” brand of idealism that sparked this show in Season 1.


24. “The Supremes” (Season 5, Episode 17). 

An running gag of Seasons 4 and 5 of The West Wing was that the Chief Justice of the Supreme Court, Roy Ashland, was losing his mind. This was demonstrated by him writing opinions in different metered poetry verses. After collapsing during Episode 7, the pressure is on to get Ashland, a God among liberal politicos, to resign. In “The Supremes,” another member of the Supreme Court drops dead unexpectedly. This dead Justice was a bastion of Conservative politics and no liberal nominee desired by the Bartlet White House will be approved by a Republican controlled Congress.

After witnessing a big Conservative thinker, Christopher Mulready (William Fichtner), verbally wrestle (respectfully yet passionately) with the ideal Liberal judge, Evelyn Baker Lang (Glenn Close, in a 1 episode appearance and being amazing), Toby comes up with a plan: they will replace the dead Justice with Mulready (keeping the Conservative voice of the Court intact), and Ashland will step down so that they can appoint the Liberal Lang as the first female Chief Justice of the Supreme Court. THIS is the heightened idealism that made this show great (and which is sorely lacking from the rest of Season 5). A respectful exchange of ideas aimed at improving everyone’s lot together. Not bad for Government work.


23. “Bad Moon Rising” (Season 2, Episode 19). 

Coming the week after the classic Episode, “17 People,” “Bad Moon Rising” had a lot of expectations and it really comes through. Now that President Bartlet has told Toby about his MS (who, BTW, is Hella Pissed), he needs to tell the rest of the staff AND he needs to talk to a lawyer. “Bad Moon Rising” focuses on the latter.

Enter White House Counsel, Oliver Babish (the AMAZING Oliver Platt), as prickly as previous White Counsel, Lionel Tribbey, ever was, where Tribbey was all shouts and menacing cricket bats, Platt’s plays Babish is quiet, cerebral and has an additional layer of cool aloofness. He’s the kind of “every man” who only reads Le Monde and appreciates an heirloom gavel (the “big hammer”). He handles President Bartlet’s news with a simmering anger coated in professional veneer. We’ll go on to see Babish in 8 episodes of The West Wing but “Bad Moon Rising” is the first and he makes a hell of an entrance. “What do we say? Bring it on!”

(As a side note, ALL of Oliver’s interactions with Abbey which will come over the course of the show are legend and far outdo his scenes with Jed and Leo in this episode which are pretty awesome. Watch them all if you haven’t)


22. “Undecideds” (Season 7, Episode 8). 

Watching Season 7, we suspect that Congressman Matthew Santos may be the obvious spiritual successor to Jed Bartlet. Aside from their shared Catholicism, the two men both see government as the tool by which the lives of all Americans can be improved. Though Santos and Bartlet come from very different backgrounds, it’s easy to see why Josh chooses Santos as his “new Bartlet.” None of the obvious choices in the field reach for the stars of idealized government the way Jed does, so Josh heads to Texas to find his man. Josh sees Santos as the future of the Democrat party and the man that could continue and improve upon the work done by the Bartlet Administration.

In “Undecideds,” we see that Josh’s confidence in Santos as the future isn’t as concrete as we thought. In a conversation with Toby, Toby highlights Josh’s unspoken concerns about Santos and Josh waivers. By the end of the episode, seeing how the Congressman handles the politics and humanity of the shooting, we all know that Santos is the right successor to Bartlet.

Election Day is coming fast and candidate, Matthew Santos, has grown weary of being the “brown” candidate.  His fear of being pigeonholed for being Latino is exacerbated when a Spanish cop shoots a black child. The press want Santos’ take, not because he’s a candidate for President but because he’s a Spanish candidate for President. This is to say nothing of the pre-existing strained relationship of the black community with the Santos candidacy. There is discontentment that a Spanish man is running for President before a black candidate (this predates Barack Obama by several years).  A demographic assumed to vote Democrat no longer seems certain with middle-ish of the road Vinick on the one hand and a Spanish candidate on the Democrat ticket. Matt Santos has to figure out how he can go to a pre-planned campaign stop at a black church and bring comfort and healing to all sides.

The speech he gives (see below) is the kind of speech Bartlet would have given a few seasons earlier. His words are earnest and his delivery is sincere. If you’re a Bartlet fan, Santos is the guy you want to win the next election.


21.  “He Shall, from Time to Time…” (Season 1, Episode 12). 

As President Bartlet is making final preparations for his second State of the Union address, he collapses in the Oval Office. At the same time he’s incapacitated, the Joint Chiefs brief Leo on troop movements between India and Pakistan, a powder keg waiting to blow. And, we’re also in the midst of Leo’s drug problem coming to light. This is the worst possible time for the President to get the flu. When Abbey cancels a trip and returns to the White House to nurse a sick Jed, Leo’s antennae perk up. He corners Abbey about whatever it is that she and Jed are keeping from him and she confesses that Jed has multiple sclerosis.  It’s in remission but could flare up at any time, especially when triggered by something like the flu.

Across the years that The West Wing aired, Leo and Jed demonstrated to each other the very best kind of friendship. Always having each other’s backs when the other is down, but also keeping the other in check when they fly off the handle, Leo McGarry and Josiah Bartlet have the best relationship on the show (pre-Season 5, anyway, because John Wells destroyed that relationship and made Bartlet a pod person version of himself). Anyway, after speaking with Abbey, Leo goes to visit his oldest friend in his sick bed. Watching Jed break down in tears as he apologizes for not telling Leo and Leo telling him that he still would have made him President is one of the single best moments in the history of the show. It gives me all the feels no matter how many times I see it.

“I could have been a friend.”
“You’ve been a friend.”


A double entry clip because, along with the MS reveal, “He Shall, from Time to Time …” also focused on Toby. As the President’s head speech writer, he’s pushing back against feedback on well tested phrases that he feels go against what they should be doing. In the clip below, Toby sells Josh and the President on embracing the idea of Big Government instead of running away from it. It’s the ideal that propels The West Wing’s pathos and Toby Ziegler sums it up, right here, perfectly.

“Government can be a place where people come together. And where no one gets left behind. No one … gets left behind. An instrument of good.”

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