The West Wing at 20: Ranking the 20 Best Episodes of All Time

The 20 Greatest The West Wing Episodes of All Time: Part 4

#5: Season 1, Episode 14 “Take This Sabbath Day” [February 9th, 2000]

In an episode that explored what a man of great religious conviction would do when asked to pardon a man who is spending his last night on death row, while another one finds out how his “delicate system” reacts to a night out at a bachelor party. President Bartlet meets a Priest (acting legend Karl Malden), a Rabbi (The Sopranos David Proval), and a Quaker (Oscar-winner Marlee Matlin), and begins to wonder “what the hell” is he doing here. In a powerful cameo, Malden should have won an Emmy for this guest-starring role, which would be his last before his death on July 1st, 2009.

Best Line: “I have a very delicate system.” – Josh

Factoid: This episode landed Martin Sheen an Emmy Nomination for Outstanding Lead Actor in a Drama Series.

Factoid #2: Did any of you bother to ask yourself who the actor was that plays Joey Lucas’s translator, Kenny? His name is actor Bill O’Brien, who appeared in 15 episodes during its series run.

#4: Season 2, Episode 1 & 2 “In the Shadow of the Two Gunmen Part I & Part II” [October 4th, 2000]

Everyone assumed it would be Mandy, who would be revealed as the staffer that was shot and killed when it was announced over the summer after the opening season finale that she had left the show, but we were wrong. Toby found Josh, sitting slumped next to a slab of concrete, bleeding from a gunshot wound in the abdomen.

Factoid: The term “Mandyville,” would be coined after actress Moira Kelly left the series, as many characters in later years would disappear without explanation. Mandy was seen in the final moments before the shooting in the season one finale but was nowhere to be found when the season two premiere tape rolled.

Factoid #2: Longtime collaborator and Sorkin director Thomas Schlamme won an Emmy for Outstanding Directing in a Drama Series for this episode.

Notable Guest Star: Jane Lynch plays a White House reporter asking tough questions after the shooting, former NFL player and Olympic athlete Willie Gault shows up as a Secret Service Agent assigned to the First Lady, and before her run on CSI, Jorja Fox played Secret Service Agent Gina Toscano, who was tasked with keeping the president’s daughter safe.

#3: Season 2, Episode 10 “Noel” [December 20th, 2000]

In an outstanding episode that is in-tune with Sorkin’s history as a playwright, Adam Arkin guest stars as a trauma therapist, who talks to Josh about the past few weeks, and is slowly revealed throughout the episode to have lingering post-traumatic stress. This hour is quite the achievement for the show, gracefully handling flashbacks that work exceptionally well within the plot, that led to the suspenseful finale, and its dramatic unveiling. Whitford is phenomenal here, and it might be his finest work in the series, in a handful of great ones.

Best Line: “And I was so hoping we’d have a second date.” – Josh’s response to Dr. Stanley Keworth after he tells him he is unimpressed with clever answers.

Factoid: This episode won Bradley Whitford an Emmy for Outstanding Supporting Actor in a Drama Series.

#2: Season 2, Episode 18 “Seventeen People” [April 4th, 2001]

In a show-stopping performance by Richard Schiff, as the cantankerous Toby Ziegler, he slowly begins to unravel why Vice President Hoynes plans a series of speeches that looks strangely like a run for the presidency. When he confronts Leo with his concerns, the President lets him know he has Multiple Sclerosis; of course, Toby doesn’t handle it well, and the verbal jabs start to fly, spark, as his moral outrage is an ominous test balloon on how the public may react to the news. For my money, the kind of dialogue in the episode Seventeen People does not come around often, maybe never twice, and is signature Aaron Sorkin.

Best Line: “…tell me if this is funny.” – Josh

Best Line #2: “And the walls came tumbling down” – President Bartlet

Factoid: Alison Janney does not appear in the episode. She was written out when she had to fly to England to reshoot scenes for the film The Hours.

Notable Guest Star: Only a few; three to be exact, for financial reasons — the smallest set of guest stars in an episode in the show’s history.

#1: Season 2, Episode 22 “Two Cathedrals” [May 16th,2001]

What makes Martin Sheen’s character so interesting is finding out how much you can throw at a good man to see if he ever breaks. Here, with the pressures of being President, having an incurable disease, hiding a secret from the public that must feel like a giant weight tied to his ankle, and on top of it all, losing the big sister, he found years before, who was basically family; which we only discovered after watching the episode that was The West Wing’s crowning achievement. While jumping back and forth through flashbacks, toggling the origin of the start of the Jed Bartlet and Dolores Landingham relationship in its infancy, while the staff waits to see if their boss is indeed going to run for reelection, it all leads up to a climax that many misinterpreted as a cliffhanger, but really wasn’t if you were paying attention. Two Cathedrals” is simply one of the finest hours of television ever produced.

Best Line: You can google the entire speech from Martin Sheen in the cathedral.

Notable Guest Star #1: The American television pundit and host of Morning Joe, Lawrence O’Donnell, was a long-time aide to the Senator of NY, Patrick Moynihan, initially a consultant on the show (while increasing his role as a writer and producer later in the series), played the President’s father in the flashback scenes.

Notable Guest Star #2: Kirsten Nelson guest stars as the young Mrs. Landingham, who went on to work with Dule Hill in the USA Network show, “Psych,” a year after The West Wing ended.

And with that, I’ll ask, “What’s next?”

If you enjoyed this list of the definitive ranking of The 20 Greatest The West Wing Episodes of All Time, be sure to check out some of the author’s other chunky features, such as his mammoth ranking of every episode of The Sopranos, a list of the very best road trip movies ever made, his 25-year anniversary list of the greatest individual episodes of Friends, or his Memorial Day appreciation list of the best films featuring American servicemen and women.

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M.N. Miller

M.N. Miller has been a film and television writer for Ready Steady Cut since August of 2018 and is patiently waiting for the next Pearl Jam album to come out.

3 thoughts on “The West Wing at 20: Ranking the 20 Best Episodes of All Time

  • October 6, 2019 at 7:03 am

    I have one pet peeve here, and that’s no inclusion of “In Excelsis Deo”, another fine episode featuring Toby as well as more backstory on Mrs Landingham. The final scene with the funeral, and the accompanying music (Little Drummer Boy), brings tears to my eyes, every time.

  • October 7, 2019 at 5:21 pm

    While I was reading the article, I was thinking to myself “better two cathedrals be number 1”. It might be the best television episode ever recorded.

    You say you can Google the whole church speech? I can quote it. ?

    • October 9, 2019 at 3:58 am

      You can quote the entire speech from, “Two Cathedrals?” Nice!


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