1. The Guy Who Gets Shot in The Hallway In "Terminator 2"
Terminator 2 was the first R-Rated movie I saw in the theaters, and as a child, I wasn't too scarred by the specific, graphic violence throughout the movie (certainly not to a Temple of Doom nightmare-inducing degree), but I always felt really really bad for this random sad dude walking around the back-hallways of the shopping mall who gets unceremoniously shot to death by the T-1000.
Think about it: The guy is ALREADY a professional "behind-the-scenes mall worker," which is friggin' sad enough -- the ONLY PERK of that boring dead-end life is that you don't get remorselessly shot seven times for happening to be in the same hallway as two killer robots settling a future-war.
Honorable Mention: The chubby hospital security guard who gets stabbed through the eye. Equally sad, but also pretty bad-ass, and at least the T-1000 meant to kill him. To this day I still look over my shoulder every time I use a Keurig.
2. The Backup Catcher in "A League Of Their Own"
Right before the World Series, Dottie Hinson decides to quit baseball and retire quietly with her husband, then has a cinematic change of heart and dramatically returns just in time for the decisive Game 7, and she's immediately put right back into the lineup.
This makes sense, since she's the Peaches' best player and they're already trying to win sans Marla Hooch, but still, how much does that suck for the team's backup catcher (poor, pouting Alice)? Playing six straight playoff games then getting instantly benched with the Series on the line? Only to watch Dottie 'drop' the ball on the final play? Ooof.
3. The Little Squeaky Shoe in "Who Framed Roger Rabbit?"
It's pretty well-documented that the part in Who Framed Roger Rabbit? where Judge Doom randomly grabs a little cartoon shoe and burns it to death in a vat of dip is the most needlessly tragic moment in movie history, live-action OR animated. Don't even start naming counterexamples. I SAID DON'T. All "but what about..."s will be directed to the above GIF.
R.I.P. Lil Squeaky (1988 - A Couple Seconds Later in 1988)
4. Lips Manlis in "Dick Tracy"
Lips Manlis is only in Dick Tracy for two scenes, and it's somewhat implied that he's a horrible corrupt gangster who mistreats women and probably deserves what's coming to him, but still, he gets executed via "The Bath", where he's doused with liquid cement while conscious and pleading for his life, then dropped into the river. That's one of the most brutal deaths imaginable -- HOW IS THAT ACCEPTABLE IN A PG MOVIE??? BUT THROW IN A BOOB AND IT'S INSTANTLY R?? WHAT IS YOUR ENDGAME, MOTION PICTURE RATING PEOPLE???
Anyway. I did own the Lips Manlis action figure when I was little and always felt sad for it, like the figure never knew what was about to happen to itself.
5. This Evil 'Hawks' Kid From "The Mighty Ducks"
Poor Hawks. I know they're the 'bad guys' in The Mighty Ducks because they wear black and take cheap-shots and are all somehow 2-5 feet taller than every single kid from District Five, but c'mon, they're frickin' children -- no kids are this outwardly evil, they're clearly just unfortunate puppets of their cutthroat win-at-all-costs Coach Reilly, who not only robs them of their humanity in his bloodthirsty pursuit of winning a division his team's clearly too good to be in, but also sets them up for the ultimate embarrassment when they eventually lose to The Ducks.
At least Disney had the heart to cut the scene where all the Prep School scouts watching the Hawks shook their heads and left the rink, forever dooming the kids' athletic and academic futures.
6. The Pirate in "Hook" Who Gets Thrown In The 'Boo Box'
90s movies really had an obsession with the "Look How EVIL This Villain Is" intro scene (see: The 'Dick Tracy' Bath, Alan Rickman from Robin Hood: Prince Of Thieves randomly stabbing his underling dude, etc.) and Hook was no exception, introducing the colorful, cartoony Captain Hook in classic Disney Fashion: With him ordering a random pirate to be crammed into a treasure chest and stung to death by two scorpions while the other pirates laughed and cheered. Cool movie! Can't wait til Hook stabs his child rival Rufio through the heart!
Bonus Fun Fact! That Pirate is Glenn Close!
Double Bonus Fun Fact! Still a horrifying scene.
7. Bob from Tim Burton's "Batman"
In the 1989 Batman movie, the Jack Nicholson Joker has a trusty sidekick named "Bob" who SEEMS like he's gonna be a major character: he had his own action figure, he was a major boss in the Batman Nintendo game, and then in the movie, he barely says anything or does anything then hands the Joker a gun and gets shot with it. At least he goes out as a punchline, but what a poor, useless character.
What was Bob's personal life like? Did Bob ever learn to love? Maybe he grows his own basil in his deck-garden and plays bass in a chill bar-band on Sunday nights? Not anymore though.
RIP Bob. We literally hardly knew ye.
8. Everyone on the British Airways Plane in Die Hard 2
At the end of Die Hard 2, John McClane successfully destroys Colonel Stewart's plane and foils his plan to rescue the imprisoned General Esperanza, and everyone celebrates and 'Dennis Franz Antaognist' turns nice and "Let It Snow" plays and it's a big triumphant happy ending!
EXCEPT! In the middle of the film, Colonel Stewart CRASHES AN ENTIRE BRITISH AIRWAYS FLIGHT OF INNOCENT PEOPLE. Literally hundreds of innocent people INCLUDING CHILDREN just died. The headline the next day wouldn't be "Hero Cop Defeats Freedom Fighter General Dude", it would be "TONS OF INNOCENT FUCKING PEOPLE DIE IN HORRIFIC FIERY PLANE EXPLOSION". Yes, they'd even let the headline include "fucking," cause it's that tragic.
Granted, it's not a Die Hard movie without some loss of innocent life, but it's much more digestible when it's one well-meaning businessman (aka, the only non-wacky Asian character in any movie before like 2005) and a coked-up slicktalkin' jerk.
As for the British flight passengers, though, I still offer my most heartfelt "R.I.P., motherfuckers."