Shadow Milk Cookie, as with all the esteemed Five Great Cookies, was baked by the Witches to bring forth a new era of peace, prosperity, and enlightenment for all. Bestowed upon him was the 'Virtue of Knowledge', a power unfathomable to the average Cookie, to aid him in this journey. He is referred to as 'The Master of All Knowledge,' hinting at a profound understanding of Earthbread and perhaps even beyond. Despite this, the specifics of his Virtue remain undisclosed, leaving us to speculate about the true depths of his wisdom.

For reasons untold, the Five Great Cookies, once hailed as saviors or 'Heroes' of Cookiekind, plunged into darkness and reemerged as the self-proclaimed 'Beasts.' Their descent into malevolence marked a tragic chapter in Earthbread history, as they wreaked havoc and devastation upon the land. It is strongly suggested that each of the Beasts executed mass murder in their own distinctive manner. (In regards to Shadow Milk Cookie, the initial trailer implies that this is achieved by instigating war.)

The Witches were unable to bear witness to the devastation left by the Beasts. In retaliation, they decreed punishment upon the Five, sentencing them to exile on the remote continent of Beast-Yeast. Their prison materialized in the form of The Silver Tree, the centerpiece of Faeriewood, entrusted to the guardianship of Elder Faerie Cookie. For untold eons, he dutifully safeguarded the confines of The Silver Tree as mandated by the Witches themselves.

In a series of daring escapades, Shadow Milk Cookie has made two attempts to break free from his captivity and liberate his fellow companions. - The first, dubbed 'The Great Calamity,' involved a clash between Shadow Milk and the valiant faeries of Faeriewood. Despite his relentless onslaught that resulted in the deaths of many, Shadow Milk's escape was thwarted by the convenient timing of White Lily Cookie, whose strong magic resealed the Silver Tree. - In his second bid for freedom, Shadow Milk's efforts yielded partial success as he managed to project his soul from the confines of the Tree. This partial freedom granted him the power to sow chaos and confusion throughout Faeriewood, transforming its inhabitants into unwitting participants in his whimsical play of deceit. Ultimately, his plans were foiled by the Fool-King Elder Faerie, who sacrificed himself to empower White Lily as the new Guardian of the Seal, ensuring Shadow Milk's containment once more.

When the Witches imprisoned Shadow Milk Cookie, the uncorrupted fragment of his Virtue was extracted and bestowed upon Pure Vanilla Cookie as his Soul Jam, titled the 'Light of Truth.' Simultaneously, what remained within Shadow Milk became known as the 'Darkness (unofficial) of Deceit.' As a consequence of bearing this fragment, Pure Vanilla Cookie now shares a headspace with the jester, referred to as the 'Dark Side of the Moon.' Despite being physically confined to the tree, his presence persists within this shared space, where he continuously observes his headmate's thoughts and traumas.

Shadow Milk Cookie harnesses the power of Dark Moon Magic, utilizing spells to manipulate reality and create compelling illusions that cast existential doubt upon his enemies. Most notably, he has a talent for altering the personality of any Cookie he wishes. Ensnared within his performance, these Cookies transition into a devoted audience, revering him as their captivating entertainer.

Aside from his magical acts, Shadow Milk Cookie embodies a narcissistic charismatic persona. By transitioning between a plethora of roles within the realm of entertainment, from clown to actor to playwright, he masterfully subverts the sinister undertones of his theatrical stage. This approach not only cultivates an atmosphere of joy and humor but also fosters a deep connection between him and his audience, inviting them to immerse themselves in his performances. Through hand-crafted plays, Shadow Milk weaves his narratives, blending elements of deception with traces of truth, thus leaving onlookers pondering the authenticity of his tales. Nevertheless, his influence subtly shapes the thoughts of unsuspecting Cookies, gradually eroding their sense of individuality.

Behind his playful demeanor, Shadow Milk Cookie conceals an insatiable hunger for control, orchestrating intricate schemes in anticipation of potential pitfalls. Yet, even the most meticulous of plans are susceptible to circumstance, prompting Shadow Milk to break character. His responses, even those occasionally tinged with frustration, seldom reflect the mastermind hidden underneath.

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