In the Badass Olympics, there is one badass who takes the competition, shoves a .44 Magnum into their face, growls something Batman-esque and proceeds to paint the sidewalk with their cranial matter. That man is Harry Callahan, and even if you've got a prostate the size of Antarctica, you can be damn sure you'll be pissing your pants when he comes to town.
In the first Dirty Harry film, Clint Eastwood's Callahan was an inspector for the San Francisco Police Department. When he wasn't busy killing hippies and trying to preserve what little masculinity was left in that city, he was on the trail of Scorpio, a depraved serial killer who loved to taunt the police. Since no one taunts Harry Callahan and gets away with it, he'd pretty much signed his own death warrant at that point.
As it turns out, Dirty Harry, one of the baddest motherfuckers ever to grace the screen, was inspired by this dude on the left:

Dave Toschi was, like Dirty Harry, an inspector in the San Francisco Police Department and, strangely, Dirty Harry wasn't the first--or last--time somebody would work him into a movie. The flamboyant-even-for-San-Francisco cop would serve as the inspiration for 1968's Bullitt, in which the main character (Steve McQueen's Frank Bullitt) was based on Toschi, complete with an upside-down quick-draw shoulder holster.
It was actually in the couple of years after Bullitt when Toschi would gain nationwide fame as one of the investigators tracking down the real-life Zodiac killer. For the second time, Toschi made such an impression that a Hollywood writer ran home and tried to work him into a screenplay.
Thus, in 1971, Toschi would see another fictionalized version of himself on the silver screen, in the form of Dirty Harry, where Harry hunts down the "Scorpio" killer. The difference being that while the Zodiac case never got solved, Dirty Harry finds Scorpio and kills his fucking ass.
So were filmmakers suggesting that Toschi secretly capped the Zodiac killer in his off hours and left his body floating face-down in a quarry? Not exactly. Dirty Harry writer John Milius said the whole "shoot the fucker and save on the trial" aspect of Dirty Harry was inspired by another cop, a friend of his in Long Beach who remained unnamed, probably to avoid the wrath of Internal Affairs.
Here's where it gets bizarre: In 2007, Toschi would then see himself on screen a third time, this time under his real name, played by Mark Ruffalo in David Fincher's Zodiac.
That film actually portrays the character Toschi attending a showing of Dirty Harry. The real Toschi worked as an advisor on Zodiac, which means at some point
the real Toschi attended a screening of a film portraying him, played by an actor, attending a screening of a different film portraying him, played by a different actor.
I know its not really what this thread was looking for, but I still thought it was pretty cool