Up and At Em: Is it even possible right now? (Spoiler Alert: Yes)

[Lord Anonymous]

I beat the game today with a gunslinger and then started to do a few cleanups on achievements. I don't have the Decked out or Scholar achievement, but one of those requires more grinding and the other might just require more luck (Scholar seems luck based to me, but I don't know). However, I just tried doing the Up and At Em run and even without stopping to pick up much of anything (aside from the shotgun) and running past every enemy, I couldn't manage to kill Benedict any faster than 254 seconds. That's even after using the lever in his arena that can quickly do half his health. I'm wondering if there's a shortcut or something I don't know about since I felt that I made it there pretty quickly. Might have to try another tactic, I guess, but I can't exactly make my character run any faster or anything (outside of Dash, but that would require stopping at the wizard and even then, I would have to have found it, I think).

[Ego Homini Lupus]

I haven't even begun attempting this yet but I figured the window would be tight. I suppose the good news is that it's only a 3 minute time investment per run so it shouldn't take that many tries to figure out the best strategy. I'm still working on my first "collect and do everything" run. Probably going to save Up and At Em for last. Keep us posted if you figure out a good strategy.

[Lord Anonymous]

Okay, so an update:
I am throwing myself at this right now and have found some important shortcuts that one needs to take. First: the friggin' hole in the entrance of the Edge Cave. Drop in it, but know that you will take damage and won't necessarily be able to heal all of it due to the two bandits at the top of the hole initiating combat and, thus, restricting healing. Second: Benedict has wizard bodyguards that come in once he hits a certain damage threshold. One spawns in around 75% health and the other closer to 25%. This means that the lever that can take out his health should probably be kept until at least one of these guys is brought into the fight. Third: Wizard class is fairly decent in that the fire spell can at least keep damaging Benedict while you are reloading or something. However, unlike the Gunslinger class, you only start with a revolver. You can grab the shotgun but I don't think it actually helps all that much. I will keep trying. Closest I have gotten is 184 seconds, but the RNG is really getting in the way of this one.

[Lord Anonymous]

Well, another update not long after the last one.
I did it. 166 seconds. Method:
1.) I was a Gunslinger. Marked Benny with the "Q" ability before slamming him hard with the flame shot and rapidfire capability of the repeater. NOTE: I ONLY used the repeater for this. Don't bother loading the revolver as it takes extra time. Only use one weapon or the other.
2.) As mentioned in my last post, you have to fall into the hole that leads directly into Benny's den. You will take damage, but try to slide against the wall to minimize the damage. He will not immediately react.
3.) Whittle his health down so that at least one of his wizards spawn in. This is where things get really tricky. I had a few times where Benny hid behind one of the boulders while reloading and did not get hit by the falling meteors that are activated by the lever. However, on my winning run, I got incredibly lucky when Benny decided to walk into the radius of like three of these things. He was brought down to near death and all I had to do was shoot him once to end this misery.

If you have problems with "legitimacy" or "gaming the system" then this next tip should not apply to your run. However, one can cheat the quicksave system in place. I quicksaved as soon as I entered the cave. Then, whenever I died or Benny dodged the trap, I would Alt+F4. I'm not fond of this method myself, but given how many times I died during this, it would have been even more aggravating to have to constantly make new characters for every attempt.

... I don't do speedrun achievements or anything, I have to admit. However, I felt like this was one of those I should be able to do. I don't know how I found myself actually pursuing this.

Great game, devs. The exploration was easily my favorite part. This Up and At Em bit was easily my most hated.

[Pilgrim]

Great job on completing this achievement! I'm not a speed runner, but Riot (the other dev) and I used to speed run just the first Dark Souls boss over and over to see how fast we could do it. It was so fun to us finding little tactics that could shave a second here and there, and since we were doing just the first boss, it wasn't much of an investment. I wanted something reminiscent of that when making achievements. I used a very similar tactic as you to beat it myself.

[Ego Homini Lupus]

I can confirm this strategy works. I was able to do it in 173. The deciding factor is whether you can get enough boulders to fall on him. It's also helpful if in the initial attack you can position him between the other shooter in the room and possibly the first fire wizard because sometimes he takes friendly fire and makes your job easier.

I despise speedrun achievements.