- The first Devil May Cry offers a few headaches that will lay demonic beatdowns on your ass, especially in Dante Must Die mode.
- The aptly named Nightmare, an amorphous blob that you can't even damage unless you hit the blue crystals scattered around its stage, which will solidify it and allow it to be damaged. It will also attack you with rapid fire projectiles regardless of what state he is in, which makes him difficult to counter. To make matters worse, in his blob form it is also capable of swallowing you whole to send you into another dimension; where you fight degraded versions of any of the previous bosses (Phantom, Griffon, or even Nelo Angelo). This process will take a large chunk off your health and Devil Trigger bar, and if you allow it to happen more than once, Nightmare might even enter Devil Trigger to increase its strength and regenerate for a short while. On the other hand, breaking out of the dimension does give a lot to your Devil Trigger bar and deal a large chunk of damage to the boss. And just to make it all the more tedious, you encounter this boss three times across the game, all toward the endgame.
- Nelo Angelo (a.k.a. Vergil) is already a Wake-Up Call Boss when you meet him and the second time you face him is no pushover, but his final fight is a pain. Not only he grows to about 1.5 times his normal size, his moveset (which mirrors yours, plus some) becomes stronger and faster. And if that isn't enough, he sometimes teleports outside of your reach and attacks you with Summoned Swords, which can rain down Death from Above on you or attack you like a Reverse Shrapnel from an angle. He can also summon it to spin around him to serve as a makeshift defense against your guns and damage you continuously until the swords break if you are too close to him. Have fun, Dante certainly doesn't after finding out Nelo's true identity.
- And that isn't even the hardest fight. Mundus is a whole new league of difficulty; you fight him in a gruelling three-phase battle, the first of which will force you to fly across the sky of an alternate dimension he summons, firing projectiles against the demon god while avoiding his plethora of attacks, including laser blasts, lightning and explosions. Even after forcing him back to the ground for the second phase and with the help of the Sparda Devil Trigger, his slow but powerful attacks will wreck you if you don't avoid it. Fortunately, the third phase is you against his Clipped-Wing Angel form, which is a lot easier.
- While Devil May Cry 2 is in general not so hard, some of the boss fights on Dante/Lucia Must Die can be very difficult.
- Bolverk. Not only is he fast, but he also hits hard, and his wolves Freki and Geri are both very hard to hit. Oh, and he can also block bullets, just in case you though you can just shoot him to death, like you can with most bosses in this game. Thankfully Lucia never fights him outside of Secret Rooms.
- Tateobesu is fairly easy on lower difficulties, but he is a nightmare on Lucia Must Die. The reason? The boss spends the entire fight invisible, which means no lock-on. During an underwater battle. Your best bet is to spam Cranky Bombs, and pray it swims into them. This boss holds the award of being the only boss that is actually harder to beat with Trish than it is with Lucia.
- Trismagia. First of all, melee weapons are completely useless in this fight - you better have high level guns to win. Then he splits into three heads, of which only one is vulnerable, and even then it only takes half damage. Secondly, the boss periodically throws ice pillars, which screw with lock-on, which can cause you to lose sight of which head is vulnerable. The only times the boss combines is when he is about to perform his ultimate attack, which covers pretty much the entirety of the small platform Dante/Lucia are confined to. And if you deplete his health when the heads are split? He still does the ultimate attack, and the battle doesn't end until it's finished.
- It gets even worse in the Must Die difficulties, though. If you thought this fight was annoying on Hard mode, get ready to do nothing but dodge your way out of fireballs, lightning spheres, ice chunks and so much more as Trismagia will attack you relentlessly without much breathing room to do anything. The only "good" news you get is that it doesn't go into Devil Trigger mode like most other bosses in this mode.
- Devil May Cry 3 has several, befitting the Nintendo Hard difficulty of the game.
- Cerberus, who was a major cause of returns, resales, and complaints of the difficulty of the game, followed by Agni and Rudra. Cerberus was the boss at the end of the third level (meaning if you died, you probably didn't have enough continue items and had to play the level over) and Agni and Rudra were the end of the fifth, mostly because of your lack of Devil Trigger as well as your low stats and lack of powerful moveset.
- Nevan, which is annoyingly persistent. She has electrical attacks that cause huge amounts of damage if not avoided, an attack that drains a massive amount of your health to regenerate hers, and has a regenerating bat shield, which absorbs damage separately from her health bar, meaning she can only be damaged for a certain amount of time before the shields regenerate.
- Sparda-powered Arkham, whose One-Winged Angel form is a blob with very accurate tentacle attacks and projectiles. In addition, he could submerge into the demonic waters of the stage, protecting himself from attacks and summon annoying demonic dolphins. The second phase of the fight also prevents you from using Devil Trigger and Style moves (greatly limiting your move list), while the boss will fire the aforementioned projectiles even faster, forcing a painfully slow long-range fight. It's tough, even though Vergil does help you as an ally.
- All three of Vergil's fights are absolutely brutal, and they only rank up in difficulty over time.
- The first one is tough due to the lack of Devil Trigger, coupled with Vergil's insane speed with his katana Yamato and his signature Judgment Cut, orbs of space that can cut you up regardless of your distance.
- The second one is a lot harder, because he will start using Devil Trigger whenever he can, which increases his attack, defense, speed and heals him continuously for the duration, just like yours. To make matters worse, he also uses the Beowulf gauntlets and greaves, which, while slow, is used in conjuction with his teleportation abilities to deal massive damage, in addition to his Yamato (which he will start using when his health is reduced to half).
- The third and final one is nightmarish; Vergil drops the Beowulf in favor of the Force Edge, a broad sword, which he can either use as a homing boomerang to hit you from a distance or as a way to extend his already extremely damaging sword combos. His Devil Trigger duration becomes even longer and allows him to perform Limit Break attacks (which either spams Judgment Cuts on the entire map or has him chasing you around by dropping from above and smashing your skull with his sword, before teleporting back to the air to repeat the process), and regenerating all the while. In other words, he will obliterate you if you're not extremely careful and precise, as even one small slip on your part will allow him to combo you and deal massive damage. Similarly, you have to deal as much damage as you can with precision, as he will eventually heal from all your attacks if you are not consistent.
- Oh, in DMD mode, all three fights will be even worse thanks to his use of Summoned Swords, similar to albeit not as heavily used as Nelo Angelo's back in the first game.
- In Devil May Cry 4, however, That One Boss is clearly and easily identified. In keeping with the Bishōnen Line, the rematch with Dante is way, way harder than any of the other bosses. All the other bosses have a pattern. Dante's pattern is to wait until you attempt an attack, then dodge with computerized precision and counter with an impossible-to-avoid attack. Don't even get started on what he does on higher difficulties. You can't even effectively use ranged attacks because he will deflect your bullets by shooting them out of the air. It was cool when he did it in the tutorial level, but as a real boss... ugh.
- And in an interesting twist, just as you keep all unlockables on harder unlocked difficulties, so does Dante. On unlockable difficulties, he adds weapons to his move-set that he chronologically gets later on in the story. So he's NG+ just like you.
- To its credit, though, this fight can look amazing if you get the hang of it. Nothing says "Devil May Cry" like fighting the man who made stylish combat what it is with your own equally stylish attacks. This combo video on Youtube actually ends this battle with both Nero and Dante falling at the exact same moment.
That One Boss / Devil May Cry