What is the hardest Sonic boss you ever fought?

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You mean besides BrakEggman? Then the Biolizard from SA2.
On a side note, the most annoying Sonic boss I've faced is King Boom Boo from SA2 or maybe The Death Egg 2 mini-boss as Super Tails in S3&K
 
...I don't think I've ever seen a difficult Sonic boss before (save S2GG's first boss). Especially in SRB2, they're really easy.
 
I don't have a top boss for "hardest" but a really annoying one was in sonic 1 when there was that mini boss with the lazer beam and the moving spike platforms. IIRC.
 
...I don't think I've ever seen a difficult Sonic boss before (save S2GG's first boss). Especially in SRB2, they're really easy.
This. Turn super all kill every boss without effort. (Obviously, this doesn't work in SRB2, but those are easy without super anyway.)
 
Again, that stupid Sonic 2 GG first boss comes to mind. That's not really "hard" as much as it's "cheap", though.
 
Sonic 2 GG first boss, I have never beaten it, as opposed to every other Sonic boss I've played, all of which I have beaten.
 
Never fought anything more challenging than the Sonic 2 GG first boss. Every once in a blue moon I would beat the boss, other times I would be trying to beat it for the nth time.
 
Is it considered a hard boss if getting to the boss is a lot of the challenge? If so, then maybe Sonic Spinball's last boss. Just trying to get to that boss is hard.

I haven't played any Sonic game in a long while, so I can't really remember how hard they were.
 
Dr. Robotnik, Mean Bean Machine. Unless you're a real buff for puzzle games of the "drop blocks into a pit" variety, you'll get raped repeatedly just trying to get to him, let alone beat him.

Seconding Spinball's final boss, moreso because it's really irritating than it is capable of actually killing you. Screw up a difficult shot three times and you're sent halfway back down the level again. As mentioned, just getting up there is a challenge in itself, and there's the risk of having to do he majority of it all over again if you hit those windsocks too much.

The second fight with King Arthur in Black Knight is notable, but at least beatable. Lancelot Returns, on the other hand, just displays how much of an asshole Shadow can really be when he's not pulling punches, mostly in the form of projectile and Chaos Blast spam, and the reflexes of a goddamned robot. And the sword-clash moments? **** them to hell, I've never been able to win one even once and to this day I still don't know the trick to it.

Sonic 2's final boss, not the game gear one. This is actually somewhat easy (hell, even boring) once you have the pattern figured out, but expect to lose dozens of lives learning it the hard way. The fact that it's one of relatively few bosses that expect you to win with no rings just adds to the trouble.

Dark Gaia, oh for the love of god Dark Gaia. Again, the difficulty is mostly fake. It's bad enough that we had to endure the Mighty Morphin' Power Rangers shtick, but slowly advancing through gigantic fireballs with such slugglish controls is more difficult than it sounds, and then every now and then Gaia just thows a high-damage near-undodgeable beam at you just to be a pain in the tits. Then we have QTE sequences in lieu of the two punch buttons designed specifically for this boss fight, and a hectic run through a brief Sonic section loaded with trial and error deaths and a super-strict invisible timer. Rinse and repeat two or three times and that's Dark Gaia for you.

The last two bosses of Secret Rings I recall being pretty hard, but for what reasons I can't remember right now. Just that landing the close range smackdown with Darkspines is absolutely awesome and easily makes up for whatever difficulty it throws at you.
 
Sonic and the secret rings was hard? It was pretty easy, especially the last boss.

Sonic Unleashed - I agree. Dark Gaia was a big pain in the butt. I figured if you stop blocking at the end. You can just simply run through everything (And get hurt) but manage to get by him before he launches his second laser.

Sonic 2's boss - SONIC MEGA COLLECTION GAME STATES YAYAYAYYAYAYAYYA
 
Well, lets see here.

1.Sonic Unleashed - Dark Gaia. Same as everyone else's problems, blah, blah, blah, invincible lazer, blah, blah, blah, Bad reaction time.

2.Sonic 2 Game Gear - 1st Boss. ...Oh come on, do I even have to say it?!

3.Sonic Adventure 2 Battle - Biolizard/Final Hazard. Basically a bunch of **** when you battle him and yeah, he is tedious in both outings of the game and whatnot.

4.Sonic Adventure DX Director's Cut - chaos 6/final, egg viper. All three of them are very tricky when depending on how you handle the situation, especially Viper.

5.Sonic Spball - Sega Genesis/Mega Drive. Jesus! This wa a hard boss that I still have not beaten to thi very day.

And, I think that's all of them.
 
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Absolute hardest? I'd say the entirety of Sonic 06 if I could. But chances are I can't so I'm saying Erazer Djin as I was unable to figure out how/when to attack him.
 
I remember being frustrated by Biolizard in SA2B, I still have trouble timing the jumps without falling in water and the last bit is just... I was lucky to win that one time...

There's also Erazer djinn from secret rings... until I found a time break stratagy...

King Arthur was so hard I discovered the first glitch fighting him...(Just kick instead of soul surge and sonic flys! Discovered the day after US release)
 
Alright let me think let me think....uh besides Biolizard from Sa2 , got to say the final boss for Sonic Advance 1. What makes it that frustrating to defeat him would be that he switches to a random arsenal of weapon that limits your chances of hitting him when he's open (this being a giant lazer, bombs, etc). Afterwards he's completely invincible until he chooses his next weapon.
 
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