Curb Your Enthusiasm: Series 1 (Created by Larry David, 2000)
So I had initially watched this first season a few years ago - Sarah joined me for three episodes before deciding she thought it was trash. Myself on the other hand watched the entire first season deciding, at the end, that I wanted to watch everything. I sold it - on the basis that I wuld buy the boxset and Sarah, the perfect woman and equally glutton-for-punishment, purchased the entire series for my birthday. Great times for me, not so much for Sarah who - again - after three episodes, decided, again, she hated it (despite liking Larry David in 'Whatever Works').
The Same Old Story
I think the awkward-situations-with-strange-character television shows can never be 'got' upon the first viewing. You need to understand the character in whatever context - understanding their traits and the inevitable outcome of situations. Larry David's character is constantly wound-up, but the comedy is not only in his reactions (he simply gets so angry!) but in the progression of the story. After two episodes you realise that the intelligence of Curb Your Enthusiasm is how the programme is set-up and plays out. Every single thing that happens in the first ten minutes will come back to haunt Larry. The irony in how, as you watch these first ten minutes, you can understand Larry's choices and the difficult (sometimes just obvious...) decisions he has to make. The way you can relate to him makes this set-up that much more intrinsic - but like the best comedy (and horror), you cringe throughout as you know it will go wrong, you know someone will get upset and you know Larry will take the fall... you just don't know how. Akin to horror, whereby you know the ghoul is around the corner you just don't know when it will appear and what it looks like (I think Hitchcock said something similar about horror in publicity for Psycho).
Some example perhaps. In the very first episode as Larry's very flippant comment referring to his wife as 'Hitler' has huge ramifications through Jeff's parents, the situation escalates through - as Larry simply digs a deeper hole. In fact, thats a great way to enjoy Curb - 30 minutes of Larry David digging himself into a hole. What I loved about re-watching the first episode is that, even knowing the style of the programme, the problems that arise continue to happen - in some cases with no consequence. So, again, in the first episode, Larry David, having insulted and fallen out with Richard Lewis's girlfriend turns down the dinner invite the four were due to have and, instead, goes to a meal with Cheryl and, as they sit down to eat, Richard Lewis and his girlfriend sit on a table at another section of the restaurant. You watch this and think "Oh God, what will happen now?" and nothing becomes of the situation. In fact, it simply adds to the awkward environment for the sake of Larry David. Larry David alone feels awkward and can see what could happen - but knows he can't do anything about it. This is funnier still, as we the audience are constantly in that position, whereby we simply see the situations play out and know something will happen - but can do nothing to stop it...
Having only recently started the second series, you have only a handful of long-running storys. On the whole, anyone can simply watch one episode and just see the sword fall on Larry David, but certain themes seem to continue on. 'Sour Grapes', Larrys film is constantly brought up - without anyone actually seeing footage from the film - whilst the bracelet Larry and Richard Lewis fight over recurs, as does the fight itself. These are small aspects that don't affect your watching of each episode - but from watching the series back-to-back, its a nice little pay-off.
Its Not Over Yet
Most people, I have found, who like Curb Your Enthusiasm watched a random episode from the later series and then 'got into it', going back to the first series. I watched the first series first and therefore decided to get into it before having watched it (it could have gone wrong, but when you pay for something you watch it the whole way through!). Fact is, friends - Richard and Jo (from 'The Beautiful Game?' blog) - both watched a few episodes and became increasingly frustrated with the bad-acting of Larry David - and the extreme personalities of some of the side characters (the shoe guy from the second episode, the wife of Gil in the episode Porno Gil). I can appreciate this, but I think Larry David's 'acting' is more of just his character - so I personally simply 'accepted' that it was who he is. The side characters are often seen as ridiculous by Larry David- their eccentricities being the reason for Larry's exceptional frustration. I have a funny feeling that Larry's acting gets better in the following seasons and the episodes become more refined and defined int time.
Personally, I think if - like me - you enjoy The Office (More specifically, the British version) - then you should give the first series of Curb Your Enthusiasm a chance and, like the best of these, one episode is not enough. Once you have 'got' the style, set-up and characters, you'll never look back.