The West Wing 20th Anniversary – The Top 25 Best Episodes, Episodes Ranked 20-16

The West Wing 20th Anniversary
Top 25 Best Episodes
Episodes 20-16
July 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 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 is the second installment, which will tackle Episodes Ranked 20-16. You can read about the Episodes Ranked 25-21 here.

The Top 25 Episodes of The West Wing:

20.  “Election Day” (Part 2) (Season 7, Episode 17). 

John Spencer, the man who played Leo McGarry for the entire run of The West Wing, passed away right before Christmas in 2005. Leo was one of the characters carried forward into the next phase of The West Wing, joining the Matt Santos campaign as Santos’ pick for Vice President. As such, Spencer still had a significant role on the show, even as long time stars like Martin Sheen and Allison Janney had far less to do in Season 7. Executive producer, John Wells, is on record as saying that they would have tried to do one more season of the show but, when John Spencer died, all parties decided it was time to end it.

The question became, how do you say goodbye to Leo McGarry on the show? Scripts for the back end of the season were re-written and in Episode 17 of Season 7, “Election Day” (Part 2), Annabeth (Kristin Chenoweth) discovers, off screen, an unresponsive Leo. It’s election day for the Santos campaign and once she discovers Leo, the episode becomes a split narrative of election results between Vinick and Santos and the news that Leo has died in his sleep. Again, Bradley Whitford shines in this episode. Like so many of the best The West Wing episodes, Whitford’s Josh Lyman breaks our hearts with his genuinely sincere and heartfelt performances. Leo McGarry was a father figure and mentor to Josh in every way and some of the best moments on this show were their interactions, Leo scolding Josh or servicing praise and Josh always searching for Leo’s approval or trying to protect him.

From the moment that Donna tells Josh that Leo was found unresponsive, the air goes out of the room and Josh’s story becomes one of trying to process the death of his most important family member. No good videos are on YouTube from this episode but there is a scene where Donna finds Josh in Leo’s hotel room, trashed from the paramedics, where Josh is feebly trying to clean up saying he doesn’t want Mallory (Leo’s daughter) to find the room in such disrepair.  It encapsulates perfectly the heart break we ALL felt when we learn John Spencer died, a true central heart of this show.

For the raw emotion of Leo’s death juxtaposed against the unlikely win of the Santos campaign for presidency, “Election Day” (Part 2) has earned its place on our Top 25 The West Wing episodes of all time.

Photo: NBC
19.  “Manchester” (Parts 1&2) (Season 3, Episodes 2&3)

(Note: “Isaac and Ishmael” is listed as the season premiere in the official count).

Manchester, Parts 1 and 2, were the first (canonical) episodes following the “Two Cathedrals” cliffhanger. Jed had just announced his MS to the world and Season 2 ended on the reporter’s question of whether, given this startling revelation, President Bartlet would seek another term. Manchester bounces back and forth between Jed telling the reporter that yes, he was running again (and was going to win too) and the immediate aftermath of that event and 4 weeks later with the President and his staff at the Bartlet compound in Manchester planning the formal kickoff to Bartlet’s re-election campaign.

There are significant side plots involving (i) the fallout from CJ’s major gaffe during a press briefing on the Haiti situation (a possible invasion of Haiti is a background event during the President’s MS disclosure); (ii) Abbey being super pissed at Jed for announcing he was running for re-election (they had a deal for only 1 term); Josh making some political mistakes by way of over-compensating for his anger and feeling of helplessness in the wake of the MS reveal; and the introduction of campaign manager, Bruno Gianelli (Ron Silver), and his staff – brought in by Leo when the President’s polling numbers fail to rise in the aftermath of the MS disclosure. Surrounding all of this is a persistent theme of whether the President would (or should) apologize for keeping the MS from them and the country.

The West Wing specialized in dramatic Season Premieres and “Manchester” is one of those strong entries. It also makes great use of flashbacks (another The West Wing specialty) to keep the viewer on their toes. Full of tension and discord, “Manchester” thrusts the viewer into the staff’s initial elation of getting a chance to run for re-election and then the hangover the staff experiences when they realize how angry everyone really is at the President. Plus, it sets up  a Season 3, one of the best seasons of the show, perfectly!

The below clip exhibits the tension between Bruno’s people and the Senior Staff, and the general unease and tension palpable in the air. (Note: It’s not great video quality.)

18.  “Game On” (Season 4, Episode 6).

Once it was obvious that Bartlet would be running for re-election against the “every man” Governor of Florida, Robert Ritchie (James Brolin), the conflict among the Senior Staff (namely Toby) and the President was whether Jed would dumb himself down to match the simpleton that Ritchie is portrayed as or act like the intelligent statesman that he really is. The question came down to being good for all time zones (Ritchie) or being the smartest kid in the class. “Game On” was the debate episode of this election cycle. The staff spent the hour trying to come up with “10 word answers” to vastly complex political questions because this was a skill that the Ritchie camp mastered and they wanted to be able show that they could do the same. Though, they wanted to show it as a cautionary tale.  The clip below is Jed’s dissemination on the danger of trying to lead a complex country like America with ten word answers. It’s also the nail in the coffin of the Robert Ritchie campaign. Last, it’s one my favorite Bartlet monologues. All of this adds up to “Game On” earning a place in our Top 25 Episodes of All Time.

“Every once in awhile, every once in awhile, there is a day with an absolute right and an absolute wrong. But those days almost always include body counts. Other than that, there aren’t very many un-nuanced moments in leading a country that’s way to big for ten words”

17.  “Let Bartlet Be Bartlet” (Season 1, Episode 19).  

Who would have thought nominating members to the Federal Election Commission could be such a catalyst for events?!? After a season long malaise of not getting done anything they really want (besides putting Mendoza on the bench), frustration and bureaucratic impotence comes to a head in “Let Bartlet Be Bartlet.” When 2 spots on the FEC become available, President Bartlet decides to appoint Democrats as the new Commissioners, bucking how such appointments are typically handled in Washington. President Bartlet sees this as an opportunity to make headway on campaign finance reform. The B Plot features the leak of an Opposition Memo, written by Mandy during the period she didn’t work for the Bartlet administration, that lays out all of the problems and weaknesses with the Bartlet Administration. The Memo focuses on the middle of the road, non-commital posture of the administration.  The C Plot has Sam holding meetings with military brass discussing the elimination of the ban on gays in the military

These three political plotlines coalesce around the idea that President Bartlet has flights of fancy but, out of fear of jeopardizing his bid for a second term, refuses to throw his weight behind anything meaningful. Without the President’s strong and vocal backing, the staff knows that such hard political changes can never happen and worse, their opposition knows it too.

The clip below is the turning point in Season 1 and really, in the series as a whole. After Leo and Jed have a blow up about which one pulls the other to the middle of the road (an issue raised in Mandy’s memo), President Bartlet confesses that he hates the way he feels every night when he goes to bed, spinning wheels with nothing ever changing. Leo tells him its time for a new strategy and then he takes the staff “off the leash.” They may not win every battle but they’re going to give 150% no matter the case.

When people talk about the The West Wing as a font of optimism and hope that government can be a force for good in the world, THIS is the episode they are talking about, this is where it all begins.

“If we’re going to walk into walls, I want us running into them, full speed.”

16.  “Crackpots and These Women” (Season 1, Episode 5).  

A fun episode, “Crackpots and these Women” is a deserved fan favorite, known for its overall light tone. Leo has the idea that once a year, on “Big Block of Cheese Day,” the staff should interact with fringe groups that normally would not get access to senior staff at the White House. The result is the CJ deals with a group pitching a $900 million Wolves Only Highway and Sam has to deal with a UFO conspiracy theory nut.

The B Plot is about Josh being given a Continuation of Government card, detailing where he should go in case of a nuclear-type disaster that would threaten the continued existence of the American government (think: the President having to go to a bunker in case of an attack on the White House).  Josh is uneasy because he realizes that his assistant, Donna, won’t receive this kind of protection and then even more uneasy when he realizes none of his co-workers on his level (CJ, Sam, Toby) received a card either. In the course of this episode, we learn about Josh’s life long bout with guilt (over his sister’s death when he was a kid) and fear of losing his loved ones; character traits that are a recurring theme for Josh over the 7 seasons of the show. The clip below is pulled from Josh telling CJ about the card and why he’s been down all day. “Crackpots and these Women” is the first time we pull back the curtain on Josh Lyman, one of the most complex characters on the show (if not the most complex), and Bradley Whitford really lets his acting chops fly in this episode.  This performance by Whitford is what lands this episode in our Top 25 of all time. Well, that and the story of Pluie.

The C Plot deals with the introduction of Zoey, President Bartlet’s youngest daughter. A young (17-ish during this episode) Elisabeth Moss would portray Zoey over the life of the show with several significant plots involving her as well as her frequent love interest, Charlie (the President’s body man). The President uses Zoey’s arrival as an excuse to make chili for the staff throw a casual dinner party. The “These Women” part of the episode’s title comes about at the end when Jed and Leo and the other men of the West Wing discuss the cool dames that they work with. It’s also during the chili party that Josh gives back the NSA Card, telling Leo and the President that if the end comes, he doesn’t want to be separated from his friends.

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