The 10 Best Seasons of Television of the Last 20 Years

So, continuing on my rant about TV, I have decided to compile a list of THE 10 BEST SEASONS OF TELEVISION (in my lifetime). This is not the best shows, but single seasons that rung loud and delivered a lasting effect.

These are single seasons, out of longer runs. So shows that only ran for one season (Firefly, Terriers, Freaks And Geeks) wont be included. This is more where shows hit their peaks and why… Some possible spoilers ahead.

10. The Wonder Years – Season 6 (1992-1993)

The 6th and final season of THE WONDER YEARS was a perfect example of a show going out at the right time. It’s rare for a show to still be watchable in season 6, let alone to actually get stronger. Granted the ratings didn’t reflect this, (thanks 90210) but as we all know, ratings and quality are often not on the same page.

As the season, and series ended, it did so with a real sense of connection to the viewer. Kevin Arnold had become like family, and unlike most shows, THE WONDER YEARS was allowed to insert some closure. This is the first time in my life I can really remember being affected by a TV show.

Best Episode of the Season – Episode 22: Independence Day

9. The Wire – Season 1 (2002)

THE WIRE has to be one of the least watched, best shows ever. Had this been a network show it never would’ve survived, but luckily HBO puts a premium on quality. And while later seasons may have received more accolades, for my money Season 1 was the peak.

The drawn-out chess match between the Baltimore PD and Avon Barksdale (or more accurately Barksdale’s right hand man, and brain Russell ‘Stringer’ Bell) was so far superior in terms of development and pacing to any cop show on Network TV it’s embarrassing. This back and forth, alongside of the activities of one of the best characters in HBO history, Omar Little, made sure to reward anyone lucky enough to have watched it.

Best Episode of the Season – Episode 11: The Hunt

8.  The Shield – Season 4 (2005)

I have never been much of a Glenn Close fan. I don’t deny her ability, I just never liked her much. That is until she popped up on THE SHIELD, solidifying and already excellent cast, and help to Vic Mackey redeem himself to the audience.

The Shield Season 4, Vic Mackey, Glenn Close

After the strike team is dissolved, with Shane leaving, Vic needed a PR boost to keep the audience on his side. In steps new Captain Monica Rawling, who sees Vic as an asset that could be vital to doing some real good on the streets. Vic accepts the challenge and cleans up his act for a short period of time, reminding us that under the corruption, he’s still a damn good cop, albeit a dirty one.

Anthony Anderson’s ‘Antwon Mitchell’ gives us a new nemesis for the remainder of the series.

Best Episode of the Season – Episode 7: Hurt

7.  Seinfeld – Season 4 (1992-1993)

Thursday nights in the 90’s were dominated by Jerry Seinfeld. This is one of those shows where I could’ve put 2 or 3 seasons on this list, as the whole run was great, but I felt Season 4 is when they really hit their stride.

Kramer is a suspected serial killer in LA, Jerry and George pitch their idea for a “show about nothing” to NBC, and we all crave ‘Junior Mints’. We met The Virgin and The Bubble Boy, and bear witness to The Contest. This season is full of a litany of the show’s best episodes. Jerry dates Teri Hatcher (they’re real and they’re spectacular.) and Elaine sends out Christmas cards with her nipple visible. Practically every episode in this season is a classic. From The Smelly Car to The Handicap Spot, season 4 was when SEINFELD’s ratings exploded like George’s wallet. This is when it moved into the Top 30 and never dropped out after.

Best Episode of the Season – Episode 7: The Bubble Boy

6. Arrested Development – Season 2 (2004-05)

The funniest show since SEINFELD, but without the opportunity run for as long, ARRESTED DEVELOPMENT is now fondly remembered and talked about by the masses who didn’t bother to watch it while it was on. I loved it and was in constant terror that it’d be canceled at any moment. And though it ran barely 3 seasons, while it was on, it created comic gold. Season 2 gave us Tobias trying out for the Blue Man Group, George Sr. faking his own death, and a brilliant homage to Charlie Brown.

Ben Stiller cameos with maybe his best role since HEAVYWEIGHTS as Magician Tony Wonder. He is only one of a plethora of guest stars though. A list of whom includes Rob Corddry, Carl Weathers, Ed Helms, Mo Collins, Zach Braff, Ione Skye, Martin Mull, Amy Poehler, Dave Attell, Martin Short, and Julia-Louis Dreyfus as fake-blind Lawyer Maggie Lizer.

Best Episode of the Season – Episode 13: Motherboy XXX

5. The Simpsons – Season 5 (1993-1994)

Much like SEINFELD, this is a show where I could’ve thrown a dart and picked anything from Seasons 3-8 and wouldn’t have gotten much argument. This is when I really remember watching new episodes. In an era where a lot of kids my age (11 at the time) weren’t even allowed to watch THE SIMPSONS, my old man gathered us around the TV Sunday nights for family time. And for me Season 4 is when the Simpson family really hit it’s stride. They set a bar for cultural significance that now show since has done, and while it’s not the same as it ever was, it’s still maintaining its original time slot from 1989.

Season 5 gave us some of the show Best Episodes in it’s 20 year run. Cape Feare, Deep Space Homer, and Homer Loves Flanders are all included in the run.

Best Episode of the Season – Episode 4: Rosebud

4. Sons of Anarchy – Season 2 (2009)

The first season of SoA was entertaining, but not especially memorable. That is why I was so shocked when season 2 turned out to be some of the best television I’d seen in years. Jackson Teller’s MC is faced with opposition from every side as the Aryans move into Charming.

Gemma is raped, Half-Sack gets killed, and little Abel Teller’s kidnapping caps off a season that is truly balances an abundance of action with believable drama, a balancing act that was less successful in Season 3.

Best Episode of the Season – Episode 13: Na Triobloidi

3. Dexter – Season 4 (2009)

After what I considered to be a bit of a Season 3 disappointment, America’s favorite serial killer came back with the goods. In the best season of DEXTER by far, John Lithgow’s ‘Trinity’ killer provides a look at the life Dexter Morgan craves, at first anyhow.

The murder of Lundy and shooting of Deb provided ample motivation for MPD to catch Trinity, that is until we find out he’s not responsible. An incredible season is capped off with what seems like a pretty unceremonious ending as Dexter kills Trinity, that is until Dex gets home to find that wife Rita was Trinity’s last project. One of the best season enders I’ve ever seen.

Best Episode of the Season – Episode 12: The Getaway

2. 24 – Season 1 (2001-2002)

The day we met Jack Bauer is one of the greatest days in Television history.

CTU is established as an easily infiltrated super organization, that Jack is forced to repeatedly side-step in order to keep David Palmer and Jack’s own family alive. Dennis Hopper has a terrible accent, Lou Diamond Phillips gets killed REAL quick, and we learn who the biggest badass in TV history is: Jack Bauer.

The show’s dynamic format was something new, and those who watched were hooked quickly. This show kept us on edge for all 24 episodes. The pace never slowed and laid ground work for 7 seasons to follow, as well as a made for TV movie. And while the later season got bigger in terms of scale, season one’s quest to save Palmer and the Bauer women is as personal as we see Jack, and it made for great television.

Best/Worst Episode of the Season – Episode 23: 10:00 p.m.-11:00 p.m (Nina is exposed as the real mole – Nooooooooo!)

1.  The Sopranos – Season 2 (2000)

When SoA’s 2nd season was in full stride, and I was trying to explain to people how good it was, the example I used was: ” It’s reminds me of early Sopranos”.  That is as high of praise as I could think to give it. THE SOPRANOS’ first season introduced us to life in the modern mob. At times characters were outwardly reminiscent of THE GODFATHER, a glorified sense of honor and family put on as a front. But behind closed doors they seemed seedier, less likable, and more true to Scorsese’s GOODFELLAS.

When season 2 began, and we had a feel for who Tony and the rest of the family were, they gave Tony a real adversary other than himself, his sister. And once she hooks up with Richie Aprile, who just got out after ten years in prison and starts reasserting his authority.

For me, this 13-episode arc is the best in Television history.

Thanks for taking the time to check out this list and please let me know what you think in the comment section and by voting in the poll below.

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14 thoughts on “The 10 Best Seasons of Television of the Last 20 Years”

  1. Great List! Takes me back to a better time in TV, although shamefully I haven’t seen half these shows, but I’m Canadian, so yea, take that however you want. I’m surprised that all those great Seinfeld episodes were in one season, talk about a great year for the show.

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  2. Good list but IMO you are missing a few things:
    – Carnivale Season 2: Most underrated show ever, and how they did season 2 was just perfection.
    – Oz Season 2: Not much to be said really, awesome show and season 2 as the best imo.
    Deadwood Season 1: Western tv show done to perfection, season one could not be better in anyway, its a real shame that this show ended when it did. The characters, acting and direction in season 1 is just perfect.

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    1. I loved CARNIVALE, but I couldn’t put up a show with no ending. Season 2 was awesome, but with no closure it’s hard to say the buildup paid off. But that’s not their fault as much as HBO’s. And as much as I loved OZ, there wasn’t one season in particular that really stood out to me.

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    1. I would put season 3 of BREAKING BAD ahead of 2, though they were both great. Also, LOST was good, but much like CARNIVALE too much was left unanswered, season didn’t feel complete. But I totally agree about 24.

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  3. Sons of Anarchy s2, really? Badly written show.
    And Shield s4… well, s5 was much better, Forest Whitaker OWNS everyone. Even Glenn Close.

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  4. Personally, I think the list misses a lot of better TV shows with stronger seasons at the expense of newer and better known shows. This would be my list and you are more than welcome to disagree with it

    Roswell Season 3 – Laugh if you want, but the show was addictive and captivating at the same time. If you’ve never seen it, then you have no idea what I’m talking about
    Jack & Bobby Season 1 – This show was amazing from start to finish and went up against American Idol in its heyday. That would explain why no one watched it
    Once and Again Season 1 – This has to be the best show that everyone has just forgotten. It’s funny how good writing and acting reflecting the drama of real life is all you need for a captivating show. Simple formula that they made work
    Life Goes On Season 4 – This is another show that too many people have forgotten that diserves a lot more credit than 24 or Dexter
    Twin Peaks Season 1 – Too bad no one remembers who killed Laura Palmer
    Murphy Brown Season 4 – Who can forget Murphy Brown vs Dan Quale…I guess you did. :)
    The Shield Season 4 – You had it right on this one for evey reason you stated
    3) Homicide Life on the Street Season 4 – Quite simply one of the best seasons on television for one of TV’s best shows
    2) Oz Season 4 – Season 4 of OZ was definately the show’s high point
    1) Sleeper Cell Season 1 – This show was criminally ignored and is definately some of the best television of the last 20 years

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    1. And since shows like LIFE GOES ON played on people’s emotions they are remembered as being better than they were simply because they elicited an emotional response. Like when Corky burned down the restaurant.

      OZ and HOMICIDE are 2 of my favorite shows of all time, but I wouldn’t say that those seasons stand out more than any other, in fact if we’re talking HOMICIDE, I’d take season 2 over 4. And TWIN PEAKS, much like CARNIVALE left too many questions unanswered to be considered a standalone. I love TWIN PEAKS, but season 1 was simply the posing of the question.

      Roswell was ok at best.

      And as far as LIFE GOES ON “diserves a lot more credit than 24 or Dexter” – Why? LIFE GOES ON was just another Drama, while 24 was one of the most original shows on Television, is way more entertaining, And if you watched DEXTER than you have to admit that the 4th season stepped it up considerably, making it especially memorable. Lithgow was brilliant.

      And I didn’t forget MURPHY BROWN, but are you seriously suggesting it was anywhere near as good as SEINFELD?

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