The West Wing 20th Anniversary
Top 25 Best Episodes
Episodes 10-6
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:

10. “In Excelsis Deo” (Season 1, Episode 10). 

A lot of TV shows make a big deal out of certain Holidays (like Halloween and The Simpsons) and most shows mention Christmas in passing but The West Wing made a habit of hitting home runs with their Christmas episodes. At least the first few years. “In Excelsis Deo” set a high bar for this particular tradition and, for many fans, cemented Toby as the curmudgeon of their heart. This is also many fans’ favorite Christmas episode though, that may not be the case for me (no spoilers!).

The A plot focuses on the death of a homeless veteran. Found on the National Mall, the man died wearing a coat Toby had donated to charity and his business card was found in a pocket. When Toby (not understanding initially why he was called) arrives on the scene and sees the body still laying on the ground, hours after discovery, he inserts himself into the process. Seizing on this Korean vet’s poor treatment in death, Toby (using the President’s name without the President’s permission) arranges for a formal military funeral and burial inside Arlington Cemetery. Part of this plot involves learning that Mrs. Landingham’s two sons died in Vietnam right around Christmas.

A solid example of how fully formed The West Wing was in Season 1, “In Excelsis Deo” gives several plot lines lots of love and attention while deepening our understanding of Toby – a man who makes a career out of being rather closed off and hard to read.  It should be no surprise that this episode earned Aaron Sorkin and Rick Cleveland an Emmy for Outstanding Writing for a Drama Series, and actor Richard Schiff justly won his Emmy for Outstanding Supporting Actor in a Drama Series.

Here is the emotional peak of the episode, Toby and Mrs. Landingham attending the homeless vet’s funeral while, at the White House, a children’s chorus sings “Little Drummer Boy.”

9.  “The Last Hurrah” (Season 7, Episode 20). 

If you’ve read our ranking of the Best Seasons of The West Wing, you know I am a fan of Season 7. “The Last Hurrah” is the third to last episode of the season and shows the nitty gritty parts of the incoming Santos administration transition. Other than a few flashbacks, we never really got to see the Bartlet team getting ready to move in to the White House so it was interesting to watch with this much younger president and his team. In particular, I really enjoyed watching Helen (who I was sometimes not a fan of) fret over the changes that would ensue in her family once they become the First Family. And, most importantly for making this Best Of list, the scene below which shows Vinick and Santos discussing the role of Secretary of State.

The idea of people with different political ideologies finding common ground and having adult conversations over their differences was always a highlight of The West Wing. This late series scene reminds us of the Sorkin years, the promise of what government could be when it worked at its very best.

8.  “Midterms” (Season 2, Episode 3).  

Coming off the two hour season 2 premiere, “In the Shadow of Two Gunmen,” the bar could not have been set any higher for expectations and any follow up episode could have easily (and understandably) looked flat and unimpressive. But, “Midterms,” established the rule that The West Wing‘s Season 2 episodes were going to be among the best television ever made.  The episode covers a 12 week ramp up to the midterm elections while the White House staffers try to overcome the emotional (and for some, physical) scars of the Rosslyn shooting. The entire staff is suffering from collective PTSD and this is a tense, emotionally draining hour of television. So, at the end of the episode, when President Bartlet exorcises his personal demons via an impressive dressing down of Far Right Radio Talk show host, Dr. Jenna Jacobs (Claire Yarlett), we ALL got to take a deep restorative breath. This scene at the end of the episode was a release valve for the show and for us, the viewers. It’s a classic The West Wing moment where Sorkin let us know that all of these characters were going to be okay as they eventually worked through their issues.  I fully expect you to watch the below several times.  Chapter and Verse, bitches.

7.  “Pilot” (Season 1, Episode 1).  

A television Pilot needs to do a lot of things, very few of them having anything to do with proper narrative story telling.  As such, many pilots don’t really work as great episodes of their shows though they do often cause us to become attached as we meet (and fall in love with, or become emotionally entangled with) our characters.  The West Wing Pilot did everything a pilot needs to do, introducing us to the Bartlet administration in media res BUT ALSO, it works as a well crafted, fully formed, narrative story. This Pilot episode gives a better narrative story, with polish and class and confidence, than you get on many well established shows in their second, third or even fourth seasons. From the moment that Leo enters the North lobby and takes the first long, walk and talk steady cam shot, viewers knew that they were watching something they had never seen on TV before and maybe, would never see again.

This is to say nothing of President Bartlet’s memorable entrance at the end of the episode … one of the very best character introductions in the history of television. And, here it is for you to relive and love.

“Boy, those were the days, huh?”

6.  “Hartsfield’s Landing” (Season 3, Episode 15).  

Some of the best moments of The West Wing play like 2 person plays. Seasons 2 and 3, in particular, gave us many of these moments, often featuring President Bartlet and Toby clashing horns over the president that Toby wants Jed to be versus Jed’s own personal insecurities. “Hartsfield’s Landing” gives us one of these classic Jed and Toby moments but also teases us with President Bartlet grooming Sam for a future that we, sadly, never got to see play out.

“Hartsfield’s Landing” saw Sam “coming inside” the circle of the administration’s upper echelon of decision makers, President Bartlet’s assumption being that Sam will run for President one day and will need to think through these kinds of problems. Rob Lowe was basically gone from the show a year after this airing so we never got to see what a Seaborn presidency would have been like but, here, in “Hartsfield’s Landing,” we all got the tease of the spin-off series we hoped Aaron Sorkin would write.