Why it was infuriating:
While the early opponents were sometimes challenging, you could still find their weakness (hmmm ... that inconspicuous 'X' on his stomach, perhaps), and after that it was just a matter of timing your punches.

But, when you finally made it to Tyson (or "Mr. Dream" if you bought the game after Tyson's title defeat to Buster Douglas), no amount of Rocky-inspired runs through the city were going to save you. Mac's punches have about as much effect on the champ as a stiff breeze, which doesn't stack up well against his ability to send your teeth flying with little more than a mean thought.

Basically you had to withstand a series of withering blows from Tyson, dodging each with perfect precision (if any of his punches landed, you were done) while waiting for a window of opportunity about a quarter-second long to strike back.

Saddest moment:
Watching Mac crash to the mat following a thunderous right hook by Tyson and knowing that it was time for him to "f**k you 'til you love it." Then, realizing that to get back there you have to box every f*****g one of those guys again. No saves in this game, boys and girls.

Why it was infuriating:
The game had some general weaknesses. The fun beat-'em-up platform was interrupted by annoying surface levels, and the ridiculously unequal weapon strengths made playing as anyone other than "I can kill from across the room" Donatello seem like a waste of time. You didn't get to choose, though, you just rotated through the Turtles as they died. All of this might have been overcome by the sheer Teenage Mutant Ninja Turtle-ness of it all, if not for one stage: The Dam.

The Dam level required you to try to beat the clock through a sprawling maze in order to defuse the bombs, which were prepared to unleash the fury of the Hudson River. See that pink seaweed s**t? The stuff with an opening barely big enough for a mutated turtle to pass through? It killed you. It was ... electrified somehow. The science in the game wasn't all that accurate.

Setting aside the terrible example this set forth of telling kids the Hudson was safe to look at, let alone swim in, the failure to defuse the bombs resulted in an immediate game over, no matter how many Turtles were still alive. The margin for error was about one pixel wide and half a second long.

Saddest moment:
While it would be easy to pick on The Dam some more, we're going to have to go with the first time you make the mistake of running into one of the foot soldiers' rides while walking on the top level. You learn it doesn't just hurt you, it f*****g flattens you.

Next Turtle, please.

The premise:
Mega Man is a world-saving robot bent on destroying evildoers. Also, he consumes their souls so he can absorb their powers.

Why it was worth playing:
Mega Man is also one of the most popular video game characters ever created. It was one of the first games to include the method of "winning" new weapons and abilities as the game progressed. Nearly all of the game-play mechanics that would define the series were found here, in the original game.

Why it was infuriating:
We said "nearly" all of the game play was there. A whole lot of the features you saw in the sequels were put there to make the game easier, because the first one was nothing short of sadistic. Many of the cool upgrades were often borderline useless outside of one specific boss they were designed to be used against. Also, some of the jumping puzzles were downright evil.

And, as is unthinkable now but was common then, you couldn't save. Every time you turned on the machine, you were greeted with the same f*****g levels, which made failure a hundred times more infuriating. Every misstep meant you were about to lose a couple more hours out of your life.

Saddest moment:
As aggravating as the game could be to play, there is no more embarrassing moment in a gamer's life than the time he has to put cold hard cash on the desk, point to this game box ...

... and say, "I want that. That is right up my alley."

Why it was worth playing:
At its heart, this is basically a puzzle game, where a lot of the challenge was in moving and creating colored blocks. That sounds boring as hell, but there was a real sense of reward for solving the puzzles. This made us feel smart and dulled the sense of inadequacy we felt on a day-to-day basis. There were also lots of secrets to uncover, including multiple endings. It was advanced stuff, for the time.

Why it was infuriating:
The makers of Solomon's Key were clearly Satanists. They seemed determined to make sure the key would remain safely away from Dana's clutches, and to ensure the demons would be left free to pillage and rain destruction upon the quivering, pixilated masses. Dana is far from the world's toughest gaming hero and always seemed moments away from death. Meanwhile, his opponents often enjoyed the luxury of unlimited re-spawning.

The levels (and there were more than 60 of the bastards) were often designed so that it was entirely possible to, through bad luck, get trapped in the level with no ability to progress. You were left to commit Hara-Kiri or wait for the final cruelty to take over when Dana's timer ran out. Just like the real world, kids!

Saddest moment:
Retrieving the key, only to be told you had failed to open up all 15 hidden levels, and as such, hadn't truly defeated the game. We're not sure how many million copies of the game were sold, but we're guessing about five people in the history of the world have seen the "real" ending.

The premise:
There were some sci-fi films made in the '70s and '80s called the Star Wars trilogy (Google it; they had the actor from Firewall in them). This game was based on the second, and best, of those films.

Why it was worth playing:
This came out on two systems at the same time in 1993, the NES and the Super NES. Both had multiple game-play styles and included settings from the films.

The SNES version (right) looked less like s**t.

But, both versions were as hard as brass balls.

Why it was infuriating:
When sitting in the theaters for Empire, we can only assume the designers were intently ogling their tub of popcorn and not the screen, as they left the theaters with the impression that Luke Skywalker was incapable of functioning as a member of society, let alone as a universe-saving demi-God. The game presents you with awkward controls and requires you to find force powers. All this means it takes a massive effort just to get Luke to kill that stupid probe droid.

By 1993, gaming had advanced to the point where long-ass levels were the norm, but the whole concept of a "checkpoint" had eluded this game's creators. If you died--even at the boss--you had to drag your sorry ass all the way through entire level again.

In the end, though, the sheer impossibility of the game's design may have prevented substantial property damage by Star Wars fans. If they'd progressed, they'd have reached the part where (in the NES version) Luke rescues Han, kills Boba Fett, and, in an act of Star Wars blasphemy, defeats Darth Vader in a light saber duel. We aren't making that up.

They never brought out a Return of the Jedi game for the NES. Well, we're thinking that's why. The Empire game fucked up the storyline to the point that there was nothing for a Jedi to return from.

Saddest moment:
Discovering that crouching allows Luke to put a little extra into his jumps, and realizing that the once-menacing star pilot has been reduced to nothing better than a platform-hopping, overweight plumber.

Saddest moment:
Triumphantly making it to the game's final stage, defeating two bosses and watching your just-revived father get shot to death, only to die yourself at the hands of the final boss. Then you're propelled back to do it all again, trapping Ryu in an unending emotional roller coaster that would surely have driven him quite mad.

f**k.

Saddest moment:
Any time spent between the first moment an enemy hit you on a stage and the time you died. As demoralizing as it is to sit down to play a game knowing full well that you aren't going to beat it, simultaneously spending half that time in your underwear is downright humiliating.

Saddest moment:
The first time one of your camp counselor friends die because you failed to properly calibrate your compass to retarded Friday the 13th logic. The game uses a top-down view for its map, but gives you absolutely no indication of which direction your character is facing.

So, basically you just have to pick a direction and walk, then keep checking the map to see which way your dot is moving. Meanwhile, Jason has presumably picked up your friend in a sleeping bag and crushed him against a tree trunk.

The Konami Code was already famous by the time Contra came out (it was used in the game Gradius two years earlier) and it almost seems like the developers intentionally set the difficulty so that you'd need 30 lives to make it. For the poor bastards who had never heard of it, it wasn't if the game was going to get angrily punted across the room, but when.

Contra also forced you to share your pool of spare lives with the other player, so you were forced to pay for his retarded mistakes (something we're sure ruined many childhood friendships).

Saddest Moment:
Running through your evil foes, resolute in your 30-lives-induced superiority, and watching the extraterrestrials' island explode ... only to slowly realize that you couldn't even win a video game without cheating.