5 Chrono Cross
Although I consider Chrono Cross to be one of the greatest video games ever made (certainly better than Trigger), it's really fucking hard. Save points far away from deep dungeon bosses, a consumable magic system, and the Dario/Miguel fights make Chrono Cross the type of game that hands you unexpected game overs. You can breeze through the area monsters easily only to get your ass blown apart by a startlingly tough boss fight with a team of dwarves. Also, Chrono Cross's final boss is only defeated when you do a 12 step magic spell cast that must be done in order, very irritating.
4 Final Fantasy Tactics Advance
My favorite of the FF Tactics game, FFTA's message is simple: Plan every single move, purchase, and decision you make in advance, This game will punish you if you didn't grind your characters correctly early on, or made a job switch decision that you don't realize was incorrect until 15 hours later. To beat the game and truly excel at it's system means you must spend 80+ hours meticulously mapping out your massive partys' most intricate details. I love it because of this.
3 Lunar Silver Star Story
Lunar was so good at breaking your heart. The story was beautiful and very unique for it's time, which made it very upsetting when the game presented an unbeatable boss to roadblock your plot progression. Dungeon bosses were always difficult, always, and there were no quick exploit tricks to get you past them. Nope, the only way to win in Lunar is to grind. For hours. Sometimes you'll crawl through a dungeon for a couple hours, get spanked by the boss, and realize you need to grind 10-12 more levels to even have a shot at beating the guy. Brutal.
2 Persona 3
None of the Persona games are easy, but I found 3 particularly challenging. The bosses are few but crazy hard when they did arrive, and a couple cast high percentage instant death spells. Persona is also a game that ends when your lead character drops in a fight, not when the entire party falls. You could be two turns away from finishing a tough boss, your whole team healed up, and then one big hit to your main character and it's a game over screen. Type memorization and sheer luck are all that can do it sometimes.
1 Wild Arms
The fights could last hours. You only get the same three people in your party for the duration of the game, and they all had once-per-battle mega moves that missed. Often. The dungeons were never-ending and the weapons were expensive with money (gella) hard to come by. Wild Arms is a merciless dungeon crawler doesn't only beat the player with hard boss fights, but also demoralizes with monotony, and a 60 hour story. I beat this game, and I can't ever imagine doing it again.
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