My Beloved and I almost immediately said “The Yellowthread Street mystery Sci-Fi”, which involves a masked arsonist at a science fiction convention in Hong Kong before the Chinese takeover. Most of the books in this series are rather convoluted, but this one is the best.
Fracture, with Anthony Hopkins and Ryan Gosling, was basically this.
(Spoilers?)
So a guy fires some gunshots in his house, and the police are called to the scene, and one cop goes in and meets with the guy, and they both agree to put down their guns so the cop can check on the guy’s wife in the other room, and she turns out to have been shot; the homeowner, gun in hand, walks up on the unarmed cop who promptly overpowers him — arguably using excessive force during the beatdown, but, c’mon — and then holsters his own weapon, and is on hand when the guy confesses.
In fool-for-a-client fashion, the guy represents himself and waives everything he can to get to trial ASAP; the prosecutor, figuring it’s a slam dunk, obliges; and then we learn that what we thought was the murder weapon has never been fired. The house that’s been cordoned off is searched; no other gun is found. And the victim was cheating on her husband with that cop, who can’t get ‘impartial guy’ benefit of the doubt on anything, but the suspect gets it on if the confession is worthless if he gave it next to a guy who beat him up and had reason to want him dead.
Because the setup is: the killer had stolen the cop’s gun a while back, and swapped it for the never-fired one, and shot his wife — and then picked up the gun the cop brought in, and let the cop holster the murder weapon.
Sure, it only works if that cop is the one cop sent in. Sure, it only works if that cop doesn’t realize until too late that he’s at the home of his secret lover. Sure, it only works if that cop turns his back on the guns, having failed to notice the switcheroo before and then failing to notice the second switch later. Sure, it only works if the cop gets enraged just enough to beat the guy excessively but not enough to do it lethally. Sure, that’s not just convoluted but also contrived…
Arlington Road (1999):
In the climactic scene, the innocent protagonist races after what he thinks is a terrorist’s truck en route to bomb a federal building - only to realize too late that the vehicle is a decoy and the bomb has been planted in his own car. He’s promptly killed in the ensuing explosion and posthumously labeled a terrorist by the authorities, while the actual terrorists get off scot-free.
As Roger Ebert observed, it only makes sense if you don’t think too hard about certain questions, such as
“How can anyone, even skilled conspirators, predict with perfect accuracy the outcome of a car crash? How can they know in advance that a man will go to a certain pay phone at a certain time, so that he can see a particular truck he needs to see? How can the actions of security guards be accurately anticipated? Isn’t it risky to hinge an entire plan of action on the hope that the police won’t stop a car speeding recklessly through a downtown area?”
It’s easy if Jim Phelps plans it for them! 
Is that “Nicole [will dump Chump and Dr. Alec] and [Nicole will live happily ever after]”, or “Nicole [will dump Chump] and [Dr. Alec and Nicole will live happily ever after]”?
I really like TLD but that made me chuckle a lot!
But surely Necros has the completely convincing (cough cough) reason why Bond is essential to the plan:-
I’ve worked with the Russians. My appearance and methods are well known to them. It could jeopardize my comrades struggling for world revolution who depend upon me.
Riiiight. Maybe just, I dunno, wear a disguise? And mix it up a little? Perhaps listen to The Smiths instead of The Pretenders or something?
The second
If you read Golden Age mysteries you’ll frequently run into plots that are so improbable you wonder more how the author ever came up with them than why human beings would ever think that was a good way to commit murder.
Clayton Rawson, also a high-grade magician, had a magician detective solve bizarre crimes, bizarrely. The Footprints on the Ceiling stretches improbable to jaw-dropping levels, even for 1939. Yes, real footprints on a real ceiling on the way to a real murder.
A favorite for convoluted, though, is The Case of the Crumpled Knave by Anthony Boucher from 1942. After I finished it I needed to go back through and count. Nine crimes are committed by four separate people for multiple reasons, but mostly because Boucher stranded them on an island in a house where an unsolved murder took place 25 years earlier.
Both were highly esteemed mystery writers, BTW, and very readable. The problem with the Golden Age was that it became too much of a muchness.
You know, I actually hesitated for this very reason before posting; it’s the reason I eventually put in that bit about how the “hired killer would’ve used the exact same method to pull the trigger!”
Because, well, his “method” is to be up where a guy would work the spotlight — giving him a perfect reason to take aim at the target, while no one can actually see his “appearance’, because they’d be staring right into a damn spotlight — and then, at the moment when Necros would pull the trigger despite what he’d said, we see that Bond is likewise standing up in a high spot, where he’d likewise aimed a pistol at the target!
It’s the same method!
Only: instead of doing it where no one can get a good look at him, everyone gets to see Dalton do the gun barrel sequence!
Have His Carcass, by Dorothy Sayers, one of the Lord Peter Wimsey series.
do I need spoilers for a nearly 100 year old book? Well, just in case:
The killers plan to slit their victim’s throat. To do this they must first purchase a razor. One of them is a keen amateur actor. He spends several weeks impersonating an out of work barber, in order to persuade a real barber to sell him one.
Really, were there no shops selling razors at the time?
And then, to lure their victim to a secluded spot to do the deed, they convince him that there is a counter-revolution in Russia to reestablish the monarchy, and they want him as their new Tsar. Seriously, couldn’t they think of something less elaborate, and more plausible?
The working for weeks for a razor thing reminds me of a mystery where at the start the criminals kill a cop solely to gain access to his uniform so they then can pose as a cop for their next crime.
Feels like you can acquire a cop uniform far easier than having to kill a cop for it and suddenly making a minor crime a capital one. Nobody thought of breaking into a store that sold cop uniforms or into said cops house when he was on duty?
This is a convoluted “murder solving” film. But I think it fits.
The made for TV film Rehearsal For Murder (1982) Written by Levinson and Link, and you can smell Columbo through the whole thing.
Successful playwright Robert Preston’s fiancee committed suicide on the opening night of her new play. One year later, he has gathered together the usual suspects I mean all his friends and acquaintances ti ostensibly show them his new play, a murder mystery. The set is an exact recreation of the dead woman’s apartment, and it becomes evident that the story line is a little too close to the events of the fateful night. Preston admits yes that is so, and his wife did not commit suicide.And further, her murderer is in the theater. Wait, it’s just getting started!
Because Preston thinks he will expose the killer, he has a detective hiding in the theater. Accusations fly, eventually it is revealed the detective is actually an out of work actor because the police didn’t believe him.
At a stressful moment, a gun is pulled, shots are fired and the lights go out. The detective/actor opens a drawer in the set, pulling out a flashlight. At that point the reality of the plan is revealed. Everyone knew that the detective/actor is the true killer (!!), and the whole thing was a setup to get him to find the flashlight in the darkness, proving that he had been in the apartment. Then he would confess.
Why this is stupidly convoluted and improbable: everything hinges on the killer not only knowing that the dead woman had a flashlight in her kitchen, but where it was, in a room he was in once (and was probably stressed from the murder, after all), and he must assume the set is recreated so accurately that he’d know the flashlight was there. Now I can barely remember where my own flashlights are! I’ve been in my best friend’s house for years and I have no idea what’s in his kitchen. If the killer has not known, or simply forgotten, the whole plan would have come to a screeching halt. They had nothing after that.
But even more, look at it from “outside” the film’s story. Here you are, an unemplyed actor, a guy who murdered a famous playwright’s fiancee, and a year later he comes to you and says “I think one of my friends murdered my fiancee. Can you help me trick them into confessing?” Knowing you are the killer, would you even take part?
I saw a recent comedy sketch where a gang has just performed a successful heist and is dividing up the loot. It turned out that after paying for all the expenses they incurred in carrying out the elaborate heist, they have less than fifty dollars in profit.
Heck, I once had some of my uniforms stolen from a laundromat.
Agatha Christie’s Murder on the Orient Express - Wikipedia has a convoluted plot all right 
:
- the murder takes place on a train trapped between snowdrifts
- the murderer must be on the train (e.g. no footprints in snow)
- everybody on the train has an alibi
- the victim has been stabbed 12 times
- Hercule Poirot, a renowned detective is on the train
Couldn’t you just mock up a clip showing the route you want and play it on the victim’s hacked device? The timing would be tricky, but it sounds easier than reprogramming the entire system.
Not to mention, in addition to your bullet points, the reveal of who murdered the victim and the planning behind it was pretty darn convoluted as well.
Christie goes over-the-top in the other direction in After The Funeral: a guy dies, and at the funeral a woman states that — while it may look like natural causes — it was MURDER!!1!l!!
There’s no other reason to think it was murder; their only lead is that she, uh, said that. But then: that woman apparently gets murdered for having said that, and the only lead they really have is how she’d exclaimed that the guy was MURDERED!!1!l!! And, if that’s what’s going on, then solving his murder would be the road to solving her murder! And then: her roommate gets poisoned! Nobody seems to have any other reason to kill her, so the only lead they really have is that — well, maybe she had to be silenced, if the dead woman had maybe said something to her about the dead guy’s murder? I mean, that’s kind of the one thing that’s driving this story, right?
The convoluted murder plot involves explaining that, no, the guy wasn’t actually killed; and, well, the woman who’d said so at the funeral wasn’t actually killed either; and nobody was even trying to kill the roommate, or anyone else, with the poison that didn’t actually kill anyone…
That’s pretty close the premise of the British comedy/mystery TV series Jonathan Creek, starring stand-up comedian Alan Davies. In this case Jonathan is not a magician himself, but a technical consultant who designs illusions for a famous magician. He uses his knowledge of things like misdirection and sleight-of-hand to track down murderers, all of whom seem to be strangely conversant in those very same skills.
I used the love that. Why they bothered bringing it back a good ten years after it ended I have no idea…it was awful for the 3 or 4 episodes they bothered with.