My Top Five
1. Breaking Bad. All seasons were solid, but I think things got interesting at the end of Season 2 (with the Jane/Walt/Jesse triangle), and just proceeded to get really crazy. We actually did watch a guy with a few lurking weaknesses, when put into a complex and stressful situation, eventually "break bad," as gradual as the frog in the slowly boiling water who doesn't realize how bad things are until he gets there. Some of the bad guys were good, some of the good guys were bad; and everyone was actually some kind of "mix." It is one of the few series that I've seen where season finales/cliffhangers actually were cliffhangers and were legitimately dealt with.
I felt like the second half of season 5 meandered a bit, but the last three episodes of the series were some of the best TV I've ever seen. It's a credit to the writers, the actors, and the directors.
Best season(s): Pretty much all of them, although Seasons 3-4 really had the series locked in, and Season 5 was more the resolution of the entire show winding down.
2. Lost. Had some of the most interesting characters; introduced the idea of flashbacks (and later flashforwards) as an actual structural element of the show in order to explore characterization; and the actors were really solid, they were their characters. For some of the actors (like Terry O' Quinn, who really was John Locke), their Lost character will probably be one of the defining parts of their career, the role that everyone will remember.
It was also a show that took chances, didn't promise any character a free pass, and was willing to spin mysteries without provide easy answers. The show really explored the idea of community in a setting that could have gone far more "Lord of the Flies." I think the last season was kind of a disappointment, unfortunately, some of the resolutions of ongoing enigmas just were not as satisfying (or coherent) as the mysteries themselves. Some of the series finale was mishandled, but I think they got all the big stuff right, and for me that last half hour (coming full circle to the series opener) was so worth it.
Best season(s): The show started to get intriguing at the end of Season 1. What really made this 'must see' TV for me, though, was the beginning of the plot line with Henry Gale. Those who have seen it know which moment was just a, "OMFG!" and after that Lost just really bumped up a level. I love Charlie's arc, as he was not meant to be likable in some ways, but he was still driven by love (for Claire).
3. X-Files. I think today's television owes Fox and X-Files a round of applause, because a lot of the great TV we're getting in the 'speculative" genre stems directly from X-Files really legitimizing shows about the paranormal and exploration of faith vs science. Before then, frankly, any kind of "fantasy" show was purely light-hearted entertainment and not taken seriously dramatically (although I guess shows like "The Incredible Hulk" tried to bring some pathos to the genre). X-Files was very different; not only did it explore the kinds of mysteries Leonard Nimoy popularized over a decade before in "In Search of," but it did it in a dramatically complex way, with two lead characters with wonderful chemistry who drew in both male and female audiences. X-Files also popularized the idea of a "show mythology," in this case the ongoing arc of government conspiracy + the existence of extraterrestrial life. The show also had a host of character actor and comedian guest stars throughout its run, including Tom Noonan, Bryan Cranston, Bruce Campbell, Michael McKean, Kathy Griffin, Lily Taylor, Nora Dunn, Tony Shalhoub, etc. Many many more than I've listed, and all appropriately cast for the episode at hand.
Also of importance: Vince Gilligan got his start here and wrote some of the show's favorite episodes -- he had quite a way of mixing substantial character drama simultaneously with wry and goofy humor. It's not a surprise that he later went on to do Breaking Bad, which perfected that combination even further.
Best Season(s): Probably Season 3-6 were the best, highlighting some of the show's most famous episodes (like Pusher, Leonard Betts, etc). The show tried to struggle on when David Duchovny (and thus Fox Mulder) left, but things weren't just the same despite the strong efforts of show newcomer Robert Patrick as John Doggett; the show likely would have done better just winding down at the end of seven seasons.
4. Six Feet Under. Overseen by Alan Ball (American Beauty), the show explored life under the eaves of death (in a family-run funeral home). I didn't know any of the actors really (although Kathy Bates and Patricia Clarkson came in later, and the wonderful Lili Taylor for a season), and it had the interesting approach of the deceased dad appearing to members of his family throughout the series + the opening montage of someone always dying, sometimes in serious ways, sometimes in darkly funny ways. The show also had a strong gay character in actual gay LTRs on a show that WASN'T on Logo network nor a "gay show." The show also wasn't afraid to let its main characters be fucked up... and I don't use the word inappropriately. It was one of the first times I remember having main characters were generally positioned as 'good' but also very flawed... and some (like Nate) became even unlikable in some ways as the series progressed.
Best Season(s): I don't remember the specifics of the seasons, and I think they were all mostly on par with each other. The most important thing I could say about the show is that it has arguably the best (or in the top five) series finales ever created. It doesn't wimp out for cheap sentiment and addresses the uncertainty of life and how we humans make the best choices we can, based on our values and the things we hold dear, and then... step (or drive) forward. The last 10-15 minutes usually leave me sobbing no matter how many times I've watched it.
5. Seinfeld: I do hate putting this on here because so many people liked it, but I'm not jumping on the bandwagon, I genuinely found this show really really funny. Hilarity revolves around the absurdity of the mundane. I thought the series finale was terrible, and Jerry was actually the weakest "actor" of the bunch, but that doesn't diminish how hilarious the show could be with its main four cast stars + the amusing supporting cast. Who can forget "The Contest" or the show where George pretends to be a Marine Biologist or the great episode where jerry becomes Even Steven, George becomes successful by ignoring every one of his natural instincts, and Elaine becomes the scapegoat for the bad luck George is sloughing off?
Honorable mentions:
- The Simpsons: Started the cartoon prime-time revolution, where people finally took cartoons seriously as entertainment, some depth, and as social commentary. Futurama might be more "solid" but Simpsons started it all.
- Family Ties: This is my 'sentimental' series, I loved it when I was a kid and it just leaves me feeling good when I watch it, this was a family that loved each other. Made Michael J. Fox a star.
- Cheers: Just damned funny, and had a memorable cast. Was able to launch Frasier into its successful run, gave Woody Harrelson feet to move into a successful long movie character (with dramatic roles, wow!), gave John Ratzenberger his opening to become the Pixar voice mainstay, and even made Kirstie Alley look half-competent.