Losing your copy of the manual and not knowing how to do something
Most modern games begin with about an hour of tutorials before the action really gets started. Thats a bit too guided for some, especially when compared to old games that expected you to seriously study the manual before playing. Those booklets removed the fluff when starting a campaign, but woe be to those that misplaced the manual. You better memorize how to unequip items or unlock bombs early, because you wont have that information after your little brother misplaces the written instructions. This lack of a manual was also the pain you simply accepted when renting a game, because Nintendo actually sued rental stores to prevent them from including the official booklets.
Running out of money during the final level of an arcade game
As much as I loved arcade brawlers back in the day, they didnt love me back. Games like Double Dragon, TMNT, and Gauntlet were all designed to steal your quarters through unfair gameplay and cheap boss battles. You could tough it out to the end if you had enough money--but you had to budget properly to avoid coming up short near the end. If you ran out at the final boss, youd helplessly search your pockets for any missing cash as the Game Over counter slowly ticked down, crushing your soul with each second. The only thing worse was running off to get more change, only to return to see someone stole your spot and beat the game while you were away.
Demos were limited to discs
Using the power of the Internet to sample a game before you buy it was an impossible luxury in the days of dial-up modems. Back then, the web could barely share a 480 x 200 JPEG, so you had to either trust what you read in magazines, or seek out whatever demos Sony would put on discs for the public. Some demos came with magazines in the US and UK, others were packed in with your PlayStation system or high profile releases, and a few you simply had to buy at the store. Then again, when compared to the price of Metal Gear Solid 5: Ground Zeroes, maybe $5 for the first Parappa stage wasnt that bad after all.
Missing one disc from a set of four
Cartridges had the edge with load times, but CD games had them beat in the storage wars. If you wanted higher quality music and cutscenes, a compact disc could hold it all, though it sometimes took more than one disc to contain a massive game. That meant some games--particularly RPGs--came with the responsibility of protecting as many as five different discs. Titles spread across multiple CDs increased your odds of breaking or scratching your precious game exponentially. Misplace or damage just one of them, and youll be buying Final Fantasy 9 all over again--Squaresoft didnt sell disc 3 separately.
Getting kicked off of a fighting game by someone better
Youre safe to enjoy multiplayer games in your homes now, but when arcades were viable, you had to actually deal with other human beings to get in a few rounds of Street Fighter 2. One of the worst drawbacks to this occurred when a new challenger quartered-up. When you were moments away from beating Bison with Chun-Li, this strange challenger kicks your butt in front of whatever spectators are around. After losing two quick rounds, youre left with the choice of a hopeless rematch or slinking away in defeat, holding back tears and knowing you may never see Chun-Lis ending. Your online defeats are pretty private by comparison.
Mario Party ruining controllers (and hands)
Mario Party ultimately transformed from charming multiplayer game to over-annualized monstrosity, but the constant releases did have the bonus effect of ditching some of the early, painful minigames. Just the sight of the bicycling challenge up top will no doubt cause phantom pains in the palms of many N64 owners. However, your palms would eventually heal, while your analogue stick would be permanently scarred by the abusive circular motion Mario Party demanded. It isnt surprising that some conspiracy theorists believed Nintendo created the franchise to increase sales of replacement controllers.
Nintendo game boxes were so flimsy
Sony and Sega used the sturdy cases needed to protect the delicate CDs that held their content, while Nintendo stuck with rough and ready cartridges for all its 1990s systems. On the plus side it was much harder to scratch a copy of GoldenEye, but it also meant that the cardboard boxes SNES/N64/Game Boy games came in were treated us disposable from Nintendo. You had to be a very careful collector to keep you manual and box mint, something younger family members didnt always respect when handling your copy of Tetris Attack.
Scratching a CD is bad?
Transitioning from cartridges to compact discs wasnt easy. You could pour heap-tons of abuse on your copy of Duck Hunt with no worries, so many simply applied the same lack of care to their first copy of Ridge Racer. Turns out using your PlayStation and Saturn discs for coasters isnt such a good idea if you ever want to play them again. Hopefully you learned your lesson the first time or youd have to invest in an unreliable disc-repair kit of some kind.
Learning the hard way about save data
Heres a true life horror story: My little brother starts SaGa Frontier on PSOne, but doesnt have enough space on his only Memory Card to make a save file. The storage is filled up with massive amounts of data from games like Final Fantasy 7 and Resident Evil. The game suggests formatting the card to make room, and my brother--being unfamiliar with the term--went along with it and lost everything... all to play SaGa freaking Frontier. These are the hard lessons you had to learn in the brave new world of save data.
You had to make sure your friends didnt screen-look
When an N64 was all you had for multiplayer FPS fun in the 1990s, you had to share your view of the action with your less-than-honorable competitors. Everyones trying to enjoy a nice round of Deathmatch in the Temple map, and one player is doing good--too good. They must be screen-looking--aka, checking an opponent's corner of the four-player split-screen battle. How do you know? Because youd do the same thing to them. Dont go thinking that everyone lost their manners when shooters went online; you couldnt trust anyone to not screen-look--least of all yourself.