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

The 20 Greatest The West Wing Episodes of All Time: Part 3

#10: Season 1, Episode 22 “What Kind of Day Has it Been” [May 9th, 2000]

A few weeks after the staff let Bartlet finally be Bartlett. The season ended on the cliff-hanger of cliff-hangers, as bullets were sprayed from the sky into a group of onlookers like fireworks on the fourth by a group of Skinheads, that included the President, his staff, and his constituents.

Factoid: In all of Aaron Sorkin’s television series, the last episode in each of the first seasons is titled “What Kind of Day Has it Been.”

Notable Guest Star: Before Dr. Ken, Suzy Nakamura had a recurring role as Sam’s assistant, Cathy.


#9: Season 1, Episode 5, “The Crackpots and These Women” [October 20th, 1999] & Season 3, Episode 17, “Somebody’s Going to Emergency, Somebody’s Going to Jail” [February 28th, 2001]

The main focus of the show, at least through the Aaron Sorkin years, was that the people who work in the West Wing are concerned about serving the people, and not the government. This sentiment is told with wonderful comic touch and heartfelt exuberance with the big block of cheese day episodes that include a spunky bunch of cryptographers, wildlife experts, UFO enthusiasts, or protesters against the WTO. These episodes are the perfect genre blend of comedy and drama that are signature examples of Sorkin’s ability to juggle genres into something completely his own.

Notable Guest Star: Nick Offerman pops up as a wildlife expert who wants to spend, get this, only 900-million dollars of the taxpayer’s money to build an All-Wolves highway; that would be 1,385,977 dollars in today’s money if you adjusted it for inflation.


#8: Season 1, Episode 1 “The Pilot” [September 22nd, 1999]

The Pilot, written by Aaron Sorkin and directed by Tommy Schlamme, is practically an impeccable case study on how to start a series and set it up for success. Featuring the first walk and talk from the late veteran character actor John Spencer, the birth of a star in Alison Janney, the out-of-left-field performances of Richard Schiff and Bradley Whitford, while being headlined by Rob Lowe and Moira Kelly, The West Wing Pilot is as perfect as series-opening episodes can possibly get.

Best Line: “On the other hand, I think that five dollars are too high a price to pay for ***********.” – President Josiah Bartlet

Notable Guest Star: Before Lisa Edelstein became a “House”-hold name, she guest-starred as a DC law student who was paying her way through law school by servicing Democrats and Republicans, alike.


#7: Season 2, Episode 8 “Shibboleth” [November 22nd, 2000]

There is something about someone or something or, for instance, a show, that almost always tries to do the right thing. In Shibboleth, Sorkin and company knew when to manipulate your heartstrings and unabashedly went for the jugular, but always under the best intentions. Here, in an episode that is as timely now as it was then, the President must decide what to do with a band of men and women for China looking forward to winning a better life in the States.

Best Line: “If the Oscars were like that, I’d watch.” – President Bartlet commenting when asking why he needs to pardon two turkeys.


#6: Season 2, Episode 4 “In This White House” [October 25th, 2000]

This is the episode that got me hooked on The West Wing, so much so that it made me go back to the very beginning and find out what exactly happened in the first season by binging episodes I would watch on Bravo. In a terrific stand-alone episode, Toby and Josh attempt to help an African President, whose fictional country of Kuhndu is dying of AIDS.

Best Line: “…there’s more money to be made in a giving a white guy an erection that curing a black man of AIDS.” – Toby Zeigler explaining President Nimballa’s point to a table full of pharmaceutical executives.

Notable Guest Star: Sam Jaeger (Parenthood, The Handmaid’s Tale, The Politician) pops up as a journalist in the White House press pool.


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
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    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.

    Reply
  • October 7, 2019 at 5:21 pm
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    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. ?

    Reply
    • October 9, 2019 at 3:58 am
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      You can quote the entire speech from, “Two Cathedrals?” Nice!

      Reply

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