I've seen Hacks like Sonic Boom, Sonic Megamix, or The S Factor Sonia And Silver. But which Hack featured new bosses?
I doubt anyone has a definitive answer. I used to keep score on things like this, until around 2004, after which things just start to blur together for me. I will say, based on my knowledge of events, it was *probably* one of those you mentioned. The first new boss I personally remember was the one from Sonic Boom. But what sometimes happens, and may be the case here too, is more than one person is doing the same type of thing, and they may or may not be released in the order they were being worked. Or maybe they came out around the same time (e.g. for SAGE). So there may not even be a clear "first".
Didn’t South Island Adventure feature modified bosses? I recall that was one of the earliest notable ASM hacks, made by none other than Hivebrain, the dude who made the original disassembly of Sonic 1.
It did have some basic ASM stuff, but not custom bosses. I don't think I would've understood enough about bosses at the time. Sonic Megamix 4.0 is the first one I can think of. That was 2008 or 2009, so probably not the actual first.
It definitely wasn't Sonic Boom, my Brother Trouble hack predated that with a boss in April 2009. The Megamix 4.0 leak in this thread https://forums.sonicretro.org/index.php?threads/sonic-megamix.14121/ is dated 20th February 2009 for 4.0, but since it was a leak, it'd been earlier than this by who knows how long and I'm not sure if it counts... For S-Factor, I know there were a few bosses in development by late 2008. But nothing released until 2013, so I guess it doesn't count either... There was however a screenshot reveal of a boss in the thread https://forums.sonicretro.org/index.php?posts/283670/ 25th Feb 2009, 5 days after the Megamix leak release. However, I think Malevolence probably wins from a unique bosses ROM hack he released in 2nd November 2008 here https://forums.sonicretro.org/index.php?threads/malevolences-bosses.12645/ Unfortunately the link no longer works, I'll have to see if I can find an archieve copy. This is the hack which got him Tech Member. EDIT: Thanks to Razor & Zenon there's a video, and link in the description. If there's anything earlier than this, I wouldn't know and would be surprised too.
When did Sonic Delta get bosses? I remember they weren't in for a long time, but that hack is also ancient so time feels like it's skewed.
I had thought about mentioning Malevolence yesterday but couldn't remember when a ROM was released other than knowing that is what led to the bosses in The S Factor and a few others. New Bosses in Delta are fairly recent over the last few years, I think they previously went straight to the capsules or were just relocated copies of existing bosses (see here for a playthrough of a 2020 version). You can check https://www.neto-games.com.br/rom_hack/sonic_delta_40_mb.php for the changelog (requires translation) along with all of the older versions of it. The much earlier versions of Delta can be found here.
It's really cool to see these modified bosses. In the custom ROM I'm doing, the most I can do is change the bosses' values in the source code to make them faster to attack and/or move, for example.
I remember specifically a post on these boards along the lines of "I wish we could do custom bosses" in around 2004/2005. i.e. it hadn't been done then - 2008-ish seems reasonable(?)
The closest I can think of when it comes to original bosses made from the ground up is vladikcomper's Sonic Quick Winter Adventures. One boss in particular was made in 2009 with the red-eyed Sonic clone (always though he acted a bit like dark Link from Zelda 2): Jump to the 03:06 mark to check it out.
I always wanted to make custom boss battles. But no matter how far I got the scene just got even more out of reach. With Sonic 2 Flicky Turncoat Edition, I focused on making harder edited versions of the bosses that have a pinch mode behavior change after 8 hits, for a total of 12 hits. Not only did I not get to finish them all including editing the final boss, a lot of the pinch mode attacks either didn't work or got defeated too fast to even trigger. I mean wouldn't it be cool if all the rocks and spikes in Mystic Cave's boss fell precisely on your position and you had to weave back and forth to dodge them, controlling the fight? I could only find one video that showed that in action. If I went back and remade the entire thing, I am sure I could do much better, and including a proper Marine the Raccoon to go with it. I need to use the sprites ChelseaCatGirl made for me after all! Then there is Sonic 2 Tailsplosion: In the boss fights Tails is actually a custom new object that uses Tails' sprites that fights along vanilla Dr. Robotnik. So it is a sidekick to the boss, not the boss itself? Like the Mystic Cave Spikes, Tails falls down on your last position, covering a large vertical pillar of death. You cannot choose when Tails falls, but you do choose where he falls. So I kept adding the basic custom Tails object to the boss and make sure the fight was fair. When I hit the Metropolis Zone and Wing Fortress Zone, Sonic in the basic fight could be stuck on the side of the screen with no where to go without being hit by Robotnik's wide spinning clone eggs and Tails would unavoidably hit Sonic from above, which was a no go. So when Sonic was in these situations in the MTZ boss, Tails does an entirely different attack. One that Sonic can jump over even by standing still. Wing Fortress Zone had to have yet another Tails attack pattern that was unique to the boss. Once again, I ran out of contest time to finish the Final Boss, which would have been heavily modified to the point you wouldn't realize the parts were made from the Death Egg Robot. Wanted to include Selbi style explosion attacks and an explosion tornado that would suck Sonic in. Only got the art done. Sonic Skychaser: Here the sky chase badniks are stripped down code wise and built up into bosses in their own right. It abruptly ends because SUPRISE, there was supposed to be more. I built an entire arena afterwards that goes completely unused where you faced off of one last boss. Bosses 2 & 3 were supposed to have more attacks like boss 1, but were fine as is. Overall I need to go back and finish some of my projects, but it is hard physiologically. Like jumping into a game save of your playthrough of Skyrim 5 years ago and not knowing what you did to get you in your current position. It is easier to just start over on a new game save and only do that for a month until you have something presentable.
I just remembered what it was, you put a boss hit counter into the HUD, IIRC. Not a custom boss per-se, but still custom code relating to bosses.