Sauce on fine steak? You’re admitting this in public? Blasphemy! 
Zoolander.
You can probably just start with Season 2. The quality jump began pretty much there but once you fall in love with the show, you will probably go back and watch season 1 and enjoy it too (I did).
It’s crack I tell you!
I never saw 30 Rock except for one episode with Oprah that I didn’t think was that funny. Then I started watching it on Netflix and now it’s one of my favorite shows.
For those of you who want to start watching Parks and Recreation, I started with season 2 because I heard season 1 wasn’t that great and I don’t think I missed anything. Season 2 is hilarious. I saw the pilot episode on a plane and it definitely didn’t inspire me to keep watching.
Me too. I watched an eiosde and thought it sucked, despite the fact that I love both musicals and Jane Lynch’s acting. I recently watched the Carol Burnett episode and the Rocky Horror Glee Show, and have converted.
To be fair, everyone agreed that Big Bang had a weak premise and was barely watchable at the beginning. It was only after the actors jelled and Jim Parsons broke out as Sheldon that the show became such a hit.
It was 2Shy, the one with the guy who did online dating to find women to suck the fat out of. eww.
Buffy the Vampire Slayer. I saw the movie when it was in the theaters, thought it was OK but not great. Saw a few random episodes when it was on broadcast, and they did not pull me in. Finally got Season 1 through Netflix (thanks to all the boosters on the SDMB) and watched all the episodes in order–and got totally drawn in, so I now own all of the DVD’s.
I do think that it requires the episodes to be watched in order to allow the viewer to bond with the characters and follow the on-going plot, which was kinda revolutionary for TV in the 90’s.
Book: Wuthering Heights. It was assigned reading in high school and college. I didn’t fully “get it” until I saw the movie with Lawrence Olivier. Now it’s one of my favorite books. In essence, I was looking for heroes and villains. In this book, the hero and the villain are the same person if you look at it from one perspective. Or, from another perspective, the villain is being tortured by an even more villainous character.
Movie: Mr. and Mrs. Smith: on the first viewing, I thought it was average for an action film. However, I constantly think about themes and questions it raises about marriage and relationships. My wife is still shocked when I want to talk about part of the film in regards to our own marriage. I still don’t really like it, but I watch it whenever it’s on, because I learn something new about relationships every time I watch it. After watching it, I usually think about it for hours or days afterwards.
TV: I didn’t understand Star Trek: TNG, although I did enjoy DS9. However, when it went into syndication, I realized that each episode was a self-contained story, and that it was a character driven show like ds9. When I started watching the characters instead of the stories, the show got a lot better for me.
That was going to be my third guess, after “Squeeze.” 
Whoa, same here – I freaking love that song and think it’s the best thing Madonna’s ever written. But it doesn’t count for me for this thread, because I loved it the first time I heard it in the '80s, and I still love it now.
I’m thirding Seinfeld. I hated it when it was airing – I hate all comedy based on misunderstandings and people being awkward. Wellll, now, make that *most *comedy based on misunderstandings and people being awkward. A few months ago I was staying with my mom as she had health problems and decided to humor her Seinfeld love and watch an episode or two with her. Once I got over the fact that I didn’t have to dread the four friends’ comeuppances because they would never happen, I relaxed and noticed how well-written and cute the show was.
And George Costanza, whom I had previously written off as the most loathsome fictional character ever, became my favorite. Jason Alexander is fantastic in that role.