On September 22, 1999, NBC debuted a new political drama from master playwright and screenwriter Aaron Sorkin, detailing the behind the scenes world of the President of the United States and his senior staff. From the opening scene to the closing credits of the pilot episode, it was clear that THE WEST WING was going to be something special. The stories Sorkin told were thought-provoking looks at an idealized version of the American federal government, as told by one of the best ensemble casts ever assembled.

THE WEST WING ran for seven seasons, four of them with Sorkin at the helm, dealing with issues like gun control, the death penalty, Social Security and more. They were topics that most people would find boring, but with talented actors like Allison Janney, Richard Schiff, Rob Lowe, John Spencer, Bradley Whitford and Martin Sheen debating topics almost poetically, they became intriguing. And even after Sorkin left at the end of the fourth season, the series continued to produce thought-provoking stories with intriguing characters, though the show never reached the heights of its first four

With the advent of DVD box sets and streaming services, I am almost always in the middle of a rewatch of THE WEST WING. I’ve probably watched each of the show’s 155 episodes at least a dozen times. It’s one of my favorite shows, and I rely on it to fill odd moments of silence in my life.

I think it’s almost impossible for me to narrow down my favorite episodes of THE WEST WING down to just 20, but it’s an appropriate number for the series’ 20th anniversary. So I have compiled a list of my favorite episodes and randomly selected 10 episodes to highlight today, with 10 more to come later in the week.

Season 1

The Crackpots and These Women (Season 1, Episode 5) – It’s the series’ first “Big Block of Cheese” day, where senior staff take meetings with people that normally wouldn’t rate an appointment in the White House. The episode takes the staff out of the comfort zone that had been established over the first four episodes and establishes the show can be funny as well as it can be serious.

Let Bartlet Be Bartlet (Season 1, Episode 19) – The Bartlet administration can’t seem to have anything go right for them and morale around the West Wing is pretty low. Finally, Chief of Staff Leo McGarry (John Spencer) had enough, whipped President Bartlet (Martin Sheen) into shape and re-energizes the staff for the coming battles.

Season 2

Two Cathedrals (Season 2, Episode 22) – As he’s planning to reveal his multiple sclerosis, the president has to deal with the loss of his long-time executive secretary, Mrs. Landingham (Kathryn Joosten) and decide whether he’ll run for re-election. The second season’s final scene, as President Bartlet gets asked whether he’ll seek a second term at a press conference, is one of the greatest scenes of television ever filmed.

Season 3

Bartlet For America (Season 3, Episode 10) – An episode that mostly focuses on Leo McGarry, who’s been subpoenaed to Congress to discuss President Bartlet’s MS secret. But a Republican congressman knows some secrets about Leo and is set to reveal them to publicly embarrass him. John Spencer was the heart and soul of this series, and episodes like these showed off how great he was.

Season 4

Game On (Season 4, Episode 6) – President Bartlet debates his Republican challenger before his re-election and mops the floor with him. Meanwhile, Deputy Communications Director Sam Seaborn (Rob Lowe) goes to Orange County to talk the campaign manager of a dead congressional candidate into ending his campaign.

Inauguration Part One and Part Two – Over There (Season 4, Episodes 14&15) – OK, I’m cheating a little bit on the whole 10 episodes thing, since this is a two-parter. The episodes surround President Bartlet’s second inauguration, from the mundane issues like finding a Bible that he can use to be sworn in to a genocide in Equatorial Kuhndu. Most importantly, the staff thinks assistant Donna Moss (Janel Moloney) gave a negative quote to reporter Danny Concannon (Timothy Busfield). When Deputy Chief of Staff Josh Lyman (Bradley Whitford) figures out what’s going on, he leads a group of his coworkers to throw snowballs at her apartment window in one of my favorite scenes of the series.

Twenty-Five (Season 4, Episode 23) – The senior staff reels from the reveal that President Bartlet’s youngest daughter Zoey (Elisabeth Moss) was kidnapped after the assassination of Abdul Sharif, and the president has to make a serious decision about his future. Meanwhile, Director of Communications Toby Ziegler (Richard Schiff) takes some time to get to know his newborn twins.

Season 5

The Supremes (Season 5, Episode 17) – After a Supreme Court justice dies, the senior staff comes up with a wacky idea to install the first female Chief Justice to the Supreme Court, but they have to get the current Chief Justice to sign off on it. Glenn Close and William Fichtner guest star as potential candidates.

Season 6

King Corn (Season 6, Episode 13) – With the Primaries for a new president in full swing, the episode follows Democratic candidates Vice President Bob Russell (Gary Cole) and Congressman Matt Santos (Jimmy Smits) and Republican candidate Senator Arnold Vinick (Alan Alda) as they navigate a speech in Iowa where they’re expected to take a pledge to support ethanol.

Season 7

The Debate (Season 7, Episode 7) – Originally aired as a live episode where Santos and Vinick debated the issues in THE WEST WING‘s universe as they compete for the presidency. Sure, it’s a bit of a gimmick, but it shows off just how talented Smits and Alda are as they debate in a live setting.

That’s all for our first installment! Which episodes of THE WEST WING are your favorites? Let us know in the comments!