This show should not work.
The characters are flat.
The dialogue is unrealistic.
The plots are overly silly.
There is no development and growth.
The main main star was a terrible actor.
And everyone on the show is generally immoral and unlikeable.
This show should not work.
But it does for one simple reason: it is funny.
For the first few seasons, Seinfeld was a cookie-cutter sitcom about a group of friends living in the big city. There were some creative moments, but for the most part it was nothing terribly special, with the ratings to prove that.
But then they started taking chances by really making the show "about nothing." The show became a random series of strange experiences that elicited big laughs.
To this day, my friends and I still will randomly quote from the show like a second-hand language:
"Poppy was a little sloppy."
"She had man hands."
"As I reined blows upon him I thought 'There has to be a better way!'"
"In medieval times, they would throw you in prison just for suggesting that."
"It's the SUMMER OF GEORGE!"
"World's are colliding!"
"The Ukraine is weak!"
This was also a show that rewarded you for paying attention. In his book, Everything Bad is Good For You, Steven Johnson points out that most TV sitcoms up until this point had to have very simple, repeatable stories because of the way people watched television. But when Seinfeld became big, more and more people were collecting the episodes on VHS and were re-watching them. As a result, the show would sometimes deliver punchlines to jokes years away from the setup. And if you paid close attention and got the joke, you felt like you were in the the know.
And also Seinfeld did have an element of truth. It captured the fun, judgmental inanity of regular conversation. How often do we encounter people we don't really know and only refer to them among our friends by some quirky salient feature: Denim Vest, Close Talker, a Two-Face, "Crazy Joe," etc.? When close ranks in on our closest friends, we look at everyone outside that circle as "other," and Seinfeld captured that incredibly well. When I said that great comedy had to come from truth, I didn't mean that those truths were always nice. But there is something pleasurable about pointing at others and mocking them, otherwise people wouldn't be doing it all the time. Seinfeld let you feel that pleasure without feeling badly.
It is one of the reasons I think the finale to Seinfeld works so well. The creators were not trying to tell you that these people were role models. The fact that they freely admit to how self-absorbed these people are only contributes to the sharp insight the writers had not only on the big things, but the small things. Notice how the humor binds you to the main characters, but that affection has a limit. They are the cool social circle, not your intimate friends.
And as a Catholic, it is noticeable how the characters all go after their own selfish pursuits and are perpetually unhappy (especially George). The more they live their own way, the less happy they become. I know some Catholic hated the moment that a priest told Putty and Elaine the consequences of "just having a good time."
But what I liked about it was that the portrayal of the priest, while silly, did not have him say anything that wasn't true to Catholic teaching. It showed it in a strange and humorous way. The show was oddly respectful of religion, as when Jerry went to Confession.
In that way, Seinfeld found humor in selfish behavior without glorifying it.
"The Boyfriend/The New Friend" (3x17-18)
As I wrote above, Seinfeld took a long time to find its voice. As a result it has an incredibly long threshold. It really begins with "The Chinese Restaurant" where the group spends the entire episode waiting for a table. Here is where the show starts to realize its ability to take the simple and make it funny.
But it really discovers its personality with the two part episode where Jerry becomes friends with Keith Hernandez. This episode so clearly captures the weird experience of making a new friend as an adult man . It is a strange social and emotional mine field that should be straightforward but isn't. And it brought up so many unspoken truths about modern men. "He asked you to help him move? That's like going all the way in a guy relationship!"
And then there is the absolute silliness of the JFK-spitter storyline. It was here that the show really became what it was meant to be. They took something so small and trivial and raised it to the level of the JFK assassination while making fun of how seriously they took it.
This was the episode where it all really clicked. Soon after followed by "The Limo" episode where George and Jerry steal a limo from a guy named O'brien, who it turns out is famous to some and infamous to others.
Finally, Seinfeld had become Seinfeld.
JUMP THE SHARK
Seinfeld almost jumped the shark. At the end of the 7th season, they killed off George's fiancee Susan, to which the group reacted with nonchalance. If you were unclear about it before, this hit home that these were terrible people. The disgust that you feel towards them at the end of the season almost turns you off to the show.
But realizing this, I think, the writers realized that they needed to bring in their A-Game of humor to not lose viewers. I remember my friend, the Doctor, was a huge fan of the show but was so nonplussed by the tone, he almost stopped watching. But the returning episode had one moment that he rewound on his VHS over and over again. George felt like he was free of his dead fiancé when he gets roped into running a foundation in her name because of a quote from Star Trek II: The Wrath of Kahn. The result was hysterical.
Seinfeld was still Seinfeld. It ended when it was still humming. It ended on its own terms.
"The Opposite" (5x22)
There are so many great episodes of the show that it was difficult to choose. "The Betrayal" is a brilliant piece of writing. "The Strike" gave us the holiday of "Festivus" for the rest of us. "The Red Dot" has the funniest thing George ever said.
Seinfeld has been often imitated but it has never been duplicated. Most of the shows that tried to be like it made the mistake of taking terrible people and trying to get you to like them because they are terrible. Seinfeld never let you forget how terrible the characters were and it never apologized for them nor excused them (that's why the finale is so important to the series).
But the main reason no one has ever come close to it is because almost nothing was ever as funny.