Time out to show us how they became a supervillain/henchman?

I recall the hilarious scene in one of the Austin Powers movies where we get flashes of the extreme pain the family of mook#375 feels when Austin kills him.

Also an episode in the fairly crappy TV show Legend Of The Seeker where the hero gets to find out why one of the thousands of people he has been slaughtering became a henchman.

Any more like this?

In an early issue of the comic Invisibles, the anarchist terrorist heroes storm a government facility where they’re performing inhuman scientific experiments on homeless teenagers, in the process killing several mooks.

Maybe a year later, there’s an issue of the comic from one of the dead mooks POV, showing all the little tragedies and indignities and disappointments that led to him taking a job as a faceless guard, all leading up to the point where one of the series usual protagonists shoots him in the face.

In the original run of “the Avengers” (comic book, not TV series), the Avengers occasionally ran afoul of a villain called ‘the Taskmaster’ whose gimmick was that he trained all the henchmen and goons that other super-villains employed. The first time they encountered him was when the Wasp infiltrated a “Correctional Institute for the Criminally Insane” which was really a front for a school for training goons.

Obligatory XKCD link

I feel certain The Venture Brothers did an episode like this.

This is a game ad about a henchman for Serious Sam 3 game - “Headless Kamikaze: Screams of Glory”.

Gary the Stormtrooper from Robot Chicken deserves mention.

Syndrome spent some time explaining his backstory to Mr. Incredible in The Incredibles.

They actually SHOWED the backstory as the very first scene in the movie, too.

I feel obligated to point out that, in a long run of siily costumes, Wasp was wearing a great one in that story. If you were 13 years old and a leg man, anyway.

There’s a sequence in the video game Spec Ops: the Line where you’re shooting soldiers defending a building and your target is on the radio saying stuff like “Man, that guy just got married! Awww, not John! He knew how to make the coffee!” and other like-minded remarks about the men you’re gunning down.

I can’t find it, but Tom the Dancing Bug had a joke like that in one of the “Billy Dare” strips. Billy shoots a uniformed henchman, and there’s a brief discursion into the guy’s life, and how he’d signed up for the recruitment bonus and health plan.

What was the deal with Austin Powers? Deleted scene or something, not part of the movie? The guy who gets squished by the slow steamroller and another guy as well (sea bass?).

Johnny Sasaki from Metal Gear Solid is a nice antagonist with irritable bowel syndrome. You meet his ancestor who is similar, just trying to get by.

And maybe “Fumbles” of Cobra, and formerly GI Joe.

Skyrim: COPS shows you what the guards of Whiterun do when they’re not bitching about arrows to the knee:

And Ponda Baba from Star Wars.

Not a villain or a henchman, but a pretty minor character who would probably be disposed of without any information:

In Frederick Forsyth’s first novel The Day of the Jackal, the French policeman who sees the disguised Jackal enter the boarding house, and is subsequently dragged by Commissaire Lebel to apprehend him, when Lebel suddenly realizes the Jackal’s plan (only to get killed by the Jackal as soon as they break in on him) gets a brief flashback to a summer at the beach when we first encounter him, and a brief internal monolog when he dies. It ain’t much, but it transforms him from a cardboard target into a human being.

Unfortunately, there’s no time for that kind of thing in a movie, so in Fred Zinneman’s excellent film adaptation the [gendarme remains pretty anonymous and nameless and without backstory as he dies.

There’s a Star Wars comic that has the POV of one of the storm troopers who board the rebel transport at the beginning of episode four. He’s at the front of the assault lamenting about the strategy of trying to fit everyone through one tiny door. He’s amazed that blowing up the door actually works…thinks he’s going to survive the encounter and is killed by Princess Leia a few minutes later.

Wouldn’t the Simpsons episode “You Only Move Twice” sort of qualify?

Homer had no idea he was being hired by a supervillain when he went to work for Hank Scorpio. All he knew was that he was getting a good job with a really nice, affable boss. He didn’t know what he was really a part of.

Which raises some uncomfortable questions about the workers in those bases that James Bond is always destroying, the ones we tell ourselves “well, they were bad guys anyway”…

(Then again, there’s the “Clerks” Death Star argument…)

There’s an episode of Samurai Jack that centers on the life on one of the robot minions, the robotic assassin X9. Unique due to being given an emotion chip, he lasts longer than his brethren because he actually cares if he dies, until he’s the last. He’s long obsolete/retired and just wants to play music & hang out with his dog Lulu, but is blackmailed into fighting Jack by Aku’s threat to his dog. Despite knowing he has essentially no chance, he tracks down Jack to fight him, and Jack kills him.

Much of Soon I Will Be Invincible is about Doctor Impossible’s development into a supervillain, from his viewpoint.

And that reminds of of Doctor Horrible’s Sing-A-Long Blog, which, funny though it is, properly treats Billy’s descent into darkness as (a) a tragedy and (b) his own damn fault.