South of Midnight captivates players with a rich narrative and an expansive mythological universe, not to mention a thrilling array of boss battles enhanced by mesmerizing soundtracks. Each encounter is designed not just to challenge players, but also to immerse them deeply in the game’s enchanting world.

Although the game boasts numerous mythical beings, some encounters do not qualify as traditional boss fights due to the absence of health bars—these fleeting moments showcase creatures like the Altamaha-ha, which merely add to the ambiance without offering a full-fledged battle.

Whether you’re embarking on your journey in South of Midnight for the first time or have already emerged victorious and are eager to know which battles are deemed the toughest, this guide will provide comprehensive insights!

As someone who has navigated the entire game at the challenging Grand Weaver difficulty, I’ve compiled this list to reflect those experiences.

5. Benjy

“I Took My Hammer, My Ticket To Hell”

Location:

Chapter 4

Special Weakness:

None

Benjy may not engage in combat, yet his presence is undeniably impactful as he features a health bar, qualifying him for this list. While his fight is more about platforming than dodging attacks, Benjy serves as an excellent introduction for players to learn how to focus on wound attacks during boss engagements.

The visuals and the soundtrack while scaling Benjy are some of the most breathtaking elements of the entire game, further enriching the player’s experience.

4. Rougarou

The Most Traditional Boss Fight

Location:

Chapter 7

Special Weakness:

None

In a game populated with colossal bosses that often require specific actions before you can strike, Rougarou stands out as a traditional combat encounter. This battle features a classic arena and encourages a hit-and-dodge strategy reminiscent of Dark Souls, albeit without punishing difficulty.

While the design and buildup for Rougarou are exceptional, I managed to complete the fight nearly unscathed, which, in my opinion, somewhat diminishes its challenge factor.

3. Two-Toed Tom

A Tragic Tale for Animal Lovers

Location:

Chapter 5

Special Weakness:

Church Bell

After only a brief encounter with Two-Toed Tom in chapter 4, players finally face off against him in a much-anticipated duel in chapter 5. As the first primary boss in the game, I expected an easier fight, but was quickly challenged by his mechanics.

Damaging him requires the church bell, while his aggressive charging attacks forced me to rethink my dodging timings, leading to a frustrating reset of the battle.

Nonetheless, the moment when players enter Two-Toed Tom’s belly to conquer the infection wound is a highlight and showcases some of the best interactive storytelling in South of Midnight.

2. Kooshma

The King of Common Enemies

Location:

Chapter 13

Special Weakness:

None

As an action-adventure title, I anticipated thrilling encounters against waves of enemies, but was left disappointed to find that such sequences culminated in the final boss fight. At this stage, players have mastered the common enemy move sets and accumulated health items.

Ironically, Kooshma lacks a unique attack pattern and primarily relies on tentacle strikes and a simple dodge sequence after depleting health segments. I found myself reflecting on earlier, more invigorating battles with Huggin’ Molly and Two-Toed Tom, wondering if Kooshma could indeed deliver a grand finale.

1. Huggin’ Molly

Ignores Social Distancing

Location:

Chapter 9

Special Weakness:

Blood Vessels

From her initial introduction, Huggin’ Molly emanated a formidable aura. The challenge of navigating her arena eclipsed the actual combat, as platforming difficulties frequently sent me tumbling into the abyss.

Her move set centers around creating obstacles that hinder your mobility—a testament to her spider-like nature. After each health segment is depleted, she teleports, forcing players to engage in platforming while avoiding surprise attacks.

This dynamic makes the Huggin’ Molly encounter a seamless blend of combat and platforming challenges, culminating in what I believe to be the standout boss fight of South of Midnight.

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