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

By Marc Miller
Published: October 3, 2019 (Last updated: January 2, 2024)
The West Wing At 20: The 20 Greatest The West Wing Episodes of All Time

This ranking of the 20 greatest The West Wing episodes of all time is a multi-page feature. Please use the links at the bottom of the page to navigate through it.

1999 brought us two dramas that were influential in the entertainment landscape. One was a show that was really on no one’s radar that aired on a plucky premium cable network. They showed only someone else’s movies and was trying to create their own niche of original programming. The other had a fair amount of buzz from a very successful playwright. Who teamed with one of the hottest television producers in the nineties. They formed a partnership to bring a dull and much-maligned subject matter to a colorful network’s airwaves.

The former was The Sopranos. The latter was The West Wing. Both originally aired at various points in 1999, and they couldn’t have been more different; in fact, they were the atypical shoulder angel on one side, with the devil on the other. The Sopranos defined generations of television programs after it aired, giving birth to the Tony Soprano anti-hero tree; Walter White, Don Draper, Omar Little, Nancy Botwin, Francis Underwood, Dexter Morgan, Dr. Gregory House, and Patty Hewes couldn’t have been written without the creation of David Chase. Characters like Jed Bartlet, Josh Lyman, C.J. Cregg, Sam Seaborn, Donna Moss, Charlie Young, and Toby Ziegler, all idealistic heroes from the mind of Aaron Sorkin. These characters became passe. Practically extinct. And nowhere to be found in Hollywood. Except, 20 years later, it has become “cool” again to care openly and passionately about such things.

Simply put, good television went dark. They left behind the ideals that made The West Wing one of the last of its kind on broadcast networks that was monumentally successful. Commercially and critically. In a tribute to one of the greatest shows in television history, I have compiled a list of the top 20 episodes in the show’s seven-year run. Creating this list is like bringing home 50-60 puppies then telling 40 or more to scram. So, exceptions were made. The system was rigged. We stuffed as much West Wing goodness as one person can take. By slipping in an additional eight episodes with multiple excuses as I rationalized why it was needed.

Sadly, I still couldn’t fit in efforts like Claudia-Jean performing a number called “The Jackal.” Toby’s day of Jubilee. Why Josh’s pajamas were too big for him the entire run of the show. Danny buying the object of his affection, a goldfish. Why Mrs. Landingham feels blue around the holidays. The President’s late-night after-hours discussion on national parks. Toby asking Sam if he had tripped over something on his way into bed with a hooker. Or debating on just where did Mandy wander off to.

What I do know is that The West Wing was a show about public service. The series shaped a new generation of men and women. Who now look at that profession as a noble cause worth fighting for. In the current times we live in, Sorkin’s romantic utopian bliss was the ultimate idealistic comfort food. A show that we need back on the air more than ever. A weekly 60-minute therapy session that we would welcome back with open arms and even fuller hearts.

The 20 Greatest The West Wing Episodes of All Time: Part 1

#20: Season 6, Episode 2 “2162 Votes” [April 6th, 2005] / Season 7, Episode 16 & 17 “Election Day: Part 1 & 2” [April, 9th, 2006]

After Aaron Sorkin left, the show changed, not just in style. Still, it sorely missed the comic relief that made Sorkin’s writing so different, funny, and unexpected idealistically on network television. Seasons six and seven are dissimilar, almost a reboot if you will (I choose to look at season five as an Isaac & Ishmael-like aberration). While the laughs were left on the writing room floor compared to the first 48 episodes, the last two years were a suspenseful and interesting ride. These are the three best episodes that explored the run for the Democratic ticket and the White House; the Jimmy Smits and Alan Alda years accomplished what Sorkin never could. Show an in-depth and grassroots look at a political campaign for the presidency.

Factoid: According to Lawrence O’Donnell, a consultant on the show and later producer, the intention was for Alda’s Arnold Vinick to win. They changed the outcome after the passing of John Spencer on December 16th, 2005.

#19: Season 3, Episode 10 “Bartlet for America” [December 12th, 2001]

Every so often, Sorkin and Schlamme had an episode featuring a supporting player who made it all his own. Bradley Whitford was unforgettable in “Noel”; Richard Schiff was a tour de force in “Seventeen People”; John Spencer had his moment in Bartlet for America. While in a later episode telling the Republican counsel, “I take a bullet for the president. He doesn’t take one for me.” Everyone wishes they had an ally in our corner like Leo.

Factoid: This episode won an Emmy for Best Supporting Actor award for Spencer.

Notable Guest Star: Before Marvel made him the ultimate assistant to superheroes, Clark Gregg played an FBI Special Agent Michael Casper, who tells the president in his thirteen years with the Bureau, “…there’s no amount of money, manpower, or knowledge that can equal the person you’re looking for being stupid.”

Notable Guest Star #2: Dennis Haskins, AKA Mr. Belding, pops up as Donor #2, be careful. If you blink, you’ll miss him, and he’s practically unrecognizable.

#18: Season 1, Episode 12 “He Shall, From Time to Time” [January 12th, 2000]

In a gigantic shift, television series usually will reveal a big twist in the pilot to keep you hooked. Sorkin changes the game by revealing that after the president collapsed from what everyone thought was the flu. Which it was. However, that the president has multiple sclerosis, Mrs. Bartlett tells Leo even a fever could kill him.

Best Line: “Is it possible I’m taking something called euthanasia?” – President Bartlet

#17: Season 1, Episode 19 “Let Bartlet be Bartlet” [April 26th, 2000]

Few dramas would not just be put on display but embrace the ineptitude of their characters; That’s exactly what The West Wing did. Though, throughout the entire first season, they were stuck in the mud, so to speak, even around those hallowed halls highlighted by a speech in front of the organization of trout fishermen. With their approval rating just above our real-life current administration, the staff loved to point out that their guy was elected to the White House with less than a majority of the popular vote. Things turned around here when they Let Bartlet be Bartlet.

Best Line: “To our credit, sir, we knew it was raining once it started to rain.” – Toby explaining to the President why they were caught in the rain.

Best Line 2: “As I look over this magnificent vista…” – President Bartlet reading the speech from a prompter after they moved the event inside because of the weather.

#16: Season 2, Episode 13 & 14 “Bartlet’s Third State of the Union/The War at Home” [February 7th & 14th, 2001]

In a pair of episodes that aired separately on consecutive weeks, that can’t possibly be talked about without one another. There is a hostage situation in Columbia that the President has to resolve the night of his third state of the union address. All while the political show Capital Beat (think NBC’s Meet the Press) is broadcasting live from the White House.

Best Line: “Yeah, and it’s the BATHROBES that’s outrageous.” – C.J. to Sam after he comments how ridiculous it is that the women’s locker room has bathrobes when there are a thousand men and only around 50 women working in the White House.

The 20 Greatest The West Wing Episodes of All Time: Part 2

#15: Season 3, Episode 16 “Dead Irish Writers” [May 6th, 2002]

On the Eve of Abbey’s birthday, the news is coming down that the First Lady will lose her medical license. Why? For violating several state’s medical boards by treating her husband in secret. Amy (Mary-Louise Parker) wants to get boozy with her then write a book one day. While Donna shoots it straight. Yet, everyone comes to the same conclusion: Their men are jackasses.

Best Line: “You know, John, there are places in the world where it might be considered rude to talk about the physical attributes of another man’s wife.” – President Bartlet letting Lord John Marbury know he shouldn’t be commenting on the First Lady’s, um, assets.

Best Line #2: “If you pay close attention and stay quiet, I can teach you how to spell it.”  -Hector Elizondo (Pretty Woman) as Dr. Dalton Milgate, arrogantly telling Sam what he can teach him about the superconducting supercollider in ten minutes.

#14: Season 2, Episode 20 “18th & Potomac” [May 9th, 2001]

Few episodes can knock you over the head like a bag full of bricks. Though, this episode takes the New Hampshire Maple Syrup. It’s revealed the beloved secretary, Mrs. Landingham, was killed by a drunk driver after picking up her first brand-new car from the dealership. This is another great example of the show’s history of using smoke and mirrors before the big reveal. Leaving fans in the sense of shock, as in the episode’s final moments.

Best Line: “No, but I don’t really care that much.” – Oliver Babbish (Oliver Platt) to Abbey when she asks him if he knows what Peripheral Neuropathy indicates.

Factoid: Mrs. Landingham is played by Kathryn Joosten, the real-life mother of Peter Billingsley, who famously portrayed Ralphie in A Christmas Story.

#13: Season 4, Episode 1 & 2 “20 Hours in America: Part I & II” [September 25, 2002]

In yet another sensational, double-fisted season opener, Josh, Toby, and Donna get stranded in the middle of nowhere. Only then to realize why they loved public service in the first place.

Best Line: “The streets of heaven are too filled with angels tonight.” – President Bartlet

Notable Guest Star: Before being nominated for 4 Oscars (and being snubbed for Arrival), Amy Adams guest-starred as an Indiana farm-girl working two jobs to make all her family’s ends meet.

Notable Guest Stat #2: Before his voice broke, The Newsroom’s John Gallagher J.R. played a high-school intern with romantic entanglements and a poor sense of direction.

#12: Season 4, Episode 19 “Life on Mars” [April 30th, 2003]

This episode is best-known for the end of a story-arc for Matthew Perry, who was still on Friends and played a new White House counsel, Joe Quincy, who was responsible for taking down the Vice President Hoynes (Tim Matheson). It also features a quality guest-turn by Matheson, who portrays the perfect balance of touching melancholy and outright arrogance.

Best Line: “…the Fourth Circuit lacks the judicial imagination God gave pistachio nuts.” Joe Quincy (Perry) is repeating Toby’s line that will eventually get cleaned up by C.J.

Notable Guest Star: Grimm’s Claire Coffee pops up as a White House speechwriter intern, Cassie Tatum.

#11: Season 1, Episode 9 “The Short List” [February 16th, 2000]/Season 1, Episode 15 “Celestial Navigation” [February 16th, 2000]

Both are expertly plotted hours in a pair of episodes that focused on nominating a justice to the Supreme Court where Roberto Mendoza (Edward James Olmos) gets his “socks knocked off” by being a long-shot nominee and then refuses to sit quietly during his confirmation. Later, he gets arrested in Connecticut for, as Sam puts it, “…driving while Hispanic. While the former is played out in real-time, the latter is told in flashbacks. Josh is speaking to a group of college students at a speaking engagement. He tells the kids about his week at the White House. Even a bumbling press briefing while filling in for C.J.

Best Line: “Go into your office and come up with a secret plan to fight inflation!” – Donna

Best Line#2: “I wasn’t calling you a fool, sir. The brand new state of Georgia was.” – Sam.

Factoid: While becoming famous for it later in the series, “Celestial Navigation” was the first episode to use flashbacks.

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 finally let Bartlet be Bartlett. The season ended on the cliffhanger of cliffhangers. Bullets were sprayed from the sky into a group of onlookers. Like fireworks on the fourth. All 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]

At least through the Aaron Sorkin years, the show’s main focus was that the people who work in the West Wing are concerned about serving the people. Not the government. This sentiment is told with wonderful comic touch and heartfelt exuberance. For example, with the big block of cheese day episodes. They included 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—signature examples of Sorkin’s ability to juggle and create 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 setting up a series for success. The pilot featured the first walk and talked 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. All while being headlined by Rob Lowe and Moira Kelly. The West Wing Pilot is as perfect as series-opening episodes can get.

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

Notable Guest Star: Before Lisa Edelstein became a “House”-hold the 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 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 White House press pool journalist.

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 spending his last night on death row, 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. Malden should have won an Emmy for this guest-starring role in a powerful cameo, 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 concrete slab, 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]

An outstanding episode 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. As the show unfolds, it’s slowly revealed he is experiencing lingering post-traumatic stress throughout the episode. This hour is quite the achievement. Gracefully handling flashbacks that work exceptionally well within the plot. Which led to the suspenseful final act 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 unravels 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. 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 it 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 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. Sorkin and Schlamme toggle 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 going to run for reelection, it all leads to a climax that many misinterpreted as a cliffhanger. However, it 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), he 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 25th-anniversary list of the greatest individual episodes of Friends.