Piecemeal Funds Transfer

In the land of TV and movies, all electronic funds transfer systems work by transferring the money a little bit at a time.

We know this because while the transfer is in progress, you can clearly see a Viewer Friendly Interface displaying the amount of money, which starts at zero and quickly increases. This is apparently because the money is being stuffed, one dollar bill at at time, through the connection.

In reality, a form of fraud known as salami slicing or penny shaving exists. Often using rounding errors to steal substantial amounts of cash, often a cent at a time. Of course, the goal is to steal the cash so slowly that nobody notices. If you're going to steal a whole load of cash in the time frame of the following examples, then you may as well just steal it all in one transaction rather than slicing it up into tens of thousands of microtransactions. (Unless it's being directed at multiple accounts, though obviously it isn't feasible to have thousands of those.)

Well, unless you want to further annoy your victim with the arrival of a bank account statement several thousand pages long at the end of the month. Or annoy the bank by making them print and ship it. Or both!

Another real-life approach is structuring or smurfing: if all transactions above a certain limit ($10,000 in the United States) are reviewed by regulators as a matter of course, then a large illegal transaction may be split into several still-sort-of-large pieces that are each below the limit. To muddy the waters further, each piece may be transferred by different accomplices at different locations.

This might become Truth in Television in the future if electronic stores of value are ever implemented which would consist of individual, cryptographically signed, monetary tokens in the form of computer files. They would work in a similar fashion to electronic postage or coupon codes and if you had a large number of small denomination tokens, they would take time to transfer one by one.

Anime and Manga

 * In an early chapter of A.I. Love You, Hitoshi has to correct a bank error himself using an AI program. On his screen, he sees the balance of his account go down several yen at a time. Somewhat justified in that the process of removing the virtual money is represented as his AI avatar entering a house and taking out armfuls of bills and dumping them...

Film

 * A terrible movie featuring model Cindy Crawford (and a yacht the villains needed to hack a undersea phone line) featured this, and worse, the transaction was aborted because everything exploded before the Exact Progress Bar was finished.
 * IIRC Mission Impossible II featured a slow bank transfer with a progress bar.
 * The theft of the billions in Entrapment was shown on a progress bar. Granted, this ridiculously huge amount of money was probably stored on multiple accounts.

Video Games

 * For a game that intentionally invoke Hollywood Hacking and gleefully use Magical Computer tropes, Uplink surprisingly averts this.
 * An AI on the Citadel in Mass Effect is siphoning money from Flux. When you confront it, it both transfers its money and threatens to self-destruct, taking you with it. Shutting down the self-destruct allows you to take whatever money it couldn't shuffle away.

Western Animation

 * On The Simpsons, a character downloads money on to a floppy disk, employing this trope.

Real Life

 * Truth in Television: One man was actually caught because his program worked too fast. He hadn't thought about how much money he would actually acquire, and when his account grew beyond reasonable levels, someone wondered where all the money was coming from.
 * That is pretty much the plot of Office Space, too. Due to a rounding error, the program in that film actually transfers a dime at a time, rather than a fraction of a cent... still a small transaction, but now large enough to be noticed.
 * And of course in Office Space they point out that the same technique was used in Superman III. Which was the exact reference that sprang to mind for me at that point, too.