In addition to an engaging tale set in a detailed universe, South of Midnight also treats gamers to thrilling boss battles, which are accompanied by captivating music for added appeal.
Although numerous instances involving legendary beings occur, not every one of these can be classified as boss battles, since they lack a health bar system. Instead, they consist of brief episodes where the mythical creature’s presence is felt but not quantified. An illustration of this would be the Altamaha-ha.
Regardless if you’re embarking on your initial playthrough of South of Midnight or have finished the game and wish to learn about the most challenging boss battles, this article is designed to provide answers to those very queries!
I’ve completed the entire game at the Grand Weaver level, so I’ll be compiling this list based on that challenge.
5. Benjy
“I Took My Hammer, My Ticket To Hell”

Location | Chapter 4 |
Special Weakness | None |
As long as Benjy doesn’t assault you, his substantial health meter qualifies him for inclusion on the list.
Without anything to avoid, it’s only natural that Benjy would rank last. However, his exceptional skills as a boss in the game and the empathy players feel when defeating him make him one of the top-tier choices.
In the battle against Benjy’s boss, players are given an opportunity to familiarize themselves with the platforming challenges in South of Midnight. Simultaneously, it serves to train them on the strategy of focusing their attacks on vulnerable spots or wounds during confrontations with these boss characters.
During their journey to the summit of Benjy, players will be treated to stunning vistas and one of the finest soundtracks found anywhere within the game. Let’s make sure we don’t overlook this aspect of the adventure.
4. Rougarou
The Most Traditional Boss Fight In The Game

Location | Chapter 7 |
Special Weakness | None |
Most bosses in South of Midnight are large entities that tend to predictably attack, requiring a certain action before retaliation is possible. However, Rougarou distinguishes itself by not adhering to this norm.
In simpler terms, Rougarou is the sole boss battle that calls for an agile combat style of hitting and dodging, reminding me somewhat of a challenging boss from Dark Souls, yet fortunately it lacks the same level of toughness.
Absolutely, Rougarou often uses predictable strikes prior to transitioning into a different phase, yet those moves were among the most straightforward to avoid throughout the entire game.
Although the setup for Rougarou’s battle and its initial stages were captivating, I managed to avoid taking any damage throughout the entire fight, making me feel that it was not challenging enough, based on my personal opinion.
3. Two-Toed Tom
A Tragic Tale For Animal Lovers

Location | Chapter 5 |
Special Weakness | Church Bell |
In the following chapter, you’ll encounter the much-anticipated showdown with Two-Toed Tom, which was merely hinted at in chapter 4.
As a first-time manager, I assumed Tom would comply effortlessly, but it turned out that the situation with South of Midnight had other ideas in store for me.
Apart from causing harm to him without first ringing the church bell, his powerful jaw attacks are so tricky to avoid that I often found myself needing to restart the boss battle due to the damage incurred during my initial attempts at mastering the proper dodge timing – all while still getting accustomed to Tom’s relentless assaults.
Furthermore, one of my most enjoyed scenes in South of Midnight was when I went inside Two-Toed Tom after the battle, and eliminated the infected wound internally.
2. Kooshma
The King Of Common Enemies

Location | Chapter 13 |
Special Weakness | None |
In an action-adventure style, I expected there to be multiple instances where I’d battle waves of opponents in quick succession within the game titled South of Midnight. However, it was disheartening to learn that such intense combat sequences were saved solely for the climactic showdown against the final boss.
By now, you’ve likely committed to memory all the standard attack patterns of common foes and have all necessary healing tools at your disposal. Notably, Kooshma doesn’t possess a unique move set as such, but it does exhibit occasional tentacle attacks and a dodging sequence following the depletion of one of its health segments.
Frankly, I couldn’t suppress a sense of anticlimax. Battling against standouts like Huggin’ Molly and Two-Toed Tom, I found myself questioning, could this be the final showdown with the formidable Kooshma?
1. Huggin’ Molly
Ignores Social Distancing

Location | Chapter 9 |
Special Weakness | Blood Vessels |
As a gamer, every hint, every anticipation, and every confrontation was flawlessly designed for the chilling encounter with Huggin’ Molly. Right from her introduction, I found myself shivering under her imposing aura.
Moving through the game environment proves more challenging compared to the main battle, since the distance between platforms grows larger as you get farther from Huggin’ Molly. Countless times, I found myself tumbling into the void while attempting to leap onto the following platform.
Stepping aside, it’s evident that her fighting style primarily aims at hindering your movement in the battlefield by employing traps, much like a skillful spider does.
Or,
Moving to one side, it seems that she focuses on making it difficult for you to navigate the arena with her trap strategies, mimicking the agile moves of a spider.
After completing one of her health sections, she moves to a different location, requiring you to navigate platforms to catch up with her, all the while staying alert for any unexpected assaults she might launch.
The Huggin’ Molly boss battle seamlessly combines elements of combat and platforming, making it my preferred boss encounter within South of Midnight.
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2025-04-13 19:39