Inspired by this thread about things that start off with a weird hook but soon become conventional, how about the opposite? Media that starts off as fairly conventional, but becomes in some way wacky, weird, or way out there over time. I’m thinking of things like Community, which started off as a fairly conventional sitcom but ended up going with all sorts of parody episodes.
How about Family Matters, which, in the words of Key & Peele, was “supposed to be a blue-collar Cosby Show,” but which wound up with Steve Urkel building time machines, androids, and clones of himself?
The Bee Gees, who started out as a fairly conventional rock/pop group, but ended up making a butt load of money singing disco? That is weird!
I don’t know if you only want TV show references, but this is basically how many Stephen King novels work: you get sucked into the normality, so when he works ghosts or evil clowns into the plot, it’s more convincing and much more frightening.
In terms of TV, I’m wondering how often it’s due to the writers trying to come up with fresh plot lines or reel in dwindling audiences. I give you Mork and Mindy, a fairly conventional sitcom whose main attraction was the brilliantly frenetic Robin Williams. When that show’s audience share started tanking (It ended up in something like 50th or 60th place), they brought in Jonathan Winters as the son Mork hatched from an egg–middle-aged because Orkans age in reverse. The show was canceled at the end of that season.
Dollhouse started off as a rather conventional spy-adventure of the week show in the style of La Femme Nikita, with just the sci-fi gimmick of the spy having her memory erased and imprinted with the identity of the person she was pretending to be each time.
It evolved into a dystopian sci-fi future by the end of season 1. It was made by Joss Whedon, so we were all expecting it, but it was still a pretty dark and sharp right-turn.
Dark Shadows was never exactly conventional but when it started out it was much more like a typical soap opera. Then they introduced the ghost of Josette Collins, after that it was vampires, werewolves, Frankenstein’s monster, alternate universes mixed with time travel and even a possessed hand.
The Beatles went from Love Me Do to Revolution #9 in less than 6 years.
Hard to beat The Prisoner for this: it starts out as a spy-thriller story, and explodes in the last two episodes into exalted levels of surrealism.
(I adore it! It’s my favorite TV show. But, wow, does it follow that pattern!)
Star Trek got a little “out there” in the last season. Get Smart was always goofy, but as time went by, it got a little goofier.
Man from U.N.C.L.E. got weird…until the very last (short) season, where they tried to haul it back into something more conventional. The James Bond movies went through a similar arc: sorta standard, rollicking and weird, then something more rational again.
The final season of Roseanne went crazy.
Til Death was a mediocre sitcom until they reached their contractually obligated 4th season that nobody really wanted or cared about so they went nuts on the meta in a glorious way. The AV Club has an amazing summary, including comments by some of the people involved (although they might now be impossible to find in the new Kinja comment system).
2 Girls 1 Cup
College Football.
The web comic Questionable Content started out about the sexual tension between two millennial slackers in Northampton. one of whom had a small filthy minded robot companion who was clearly there for the lols. Other than that, it was a pretty straightforward, will they or won’t they? relationship comic. Ten years (or whatever) later, and the robots have pretty much taken over the plot lines of the comic and there’s every indication that one of the original cast members (Faye) is going to end up in a relationship with a giant ex-warbot named Bubbles. So…I guess that’s going in a weird direction?
Never had the honour of seeing it yet, myself.
So it starts off conventionally, then?
When Tommy James of the Shondells got heavily into the acid in the late 60’s he decided that his r and b hit “Mony Mony” made him into too much of a bubblegum popstar, and veered off into drugged-up psychedelia with “Crimson and Clover”.
Miley Cyrus went from a squeaky-clean Hannah Montana to lasciviously-tongued twirking.
As has been discussed a number of times here on the SDMB, the comic strip Funky Winkerbean started out as a comedy strip about high school students, and mutated into a dramatic strip which has frequently featured particularly bleak storylines.
The Drew Carey Show was a regular office comedy, and then slowly went round the bend.
Married With Children also started out fairly straight, but it didn’t take long before it turned into Three’s Company-style oddness.
You could argue Schulz’s Peanuts went in unexpected directions, but I guess it was a peculiar strip from the start, for its time at least.
When Peanuts started, it was a typical “cute kids” comic strip. It wasn’t until around its fourth or fifth year that the characters evolved into their familiar form.
I remembered that review when starting this post, but couldn’t remember the name of the series (I saw only a few episodes from early on, never reached the crazy part.)
That’s the example that first came to mind for me, a sitcom with an unexpected breakout character who ends up drawing plots toward him and his particular quirks. Arguably Happy Days went a similar route, when the Fonz (intended as a minor supporting character) gradually and shark-jumpingly became the focus.
The movie Brazil started off weird, got steadily weirder, and at some point in the middle abruptly became very very weird and remained so for the rest of the show.