Grell Sutcliffe (グレル サトクリフ Gureru Satokurifu) is a Shinigami who poses as Angelina Durless's butler and is a main antagonist during the Jack the Ripper storyline in the manga and anime. Later in the anime, he becomes a supporting deuteragonist.
Grell, as Angelina's butler, is shy, awkward and fairly ineffective at his job, ruining even simple things like tea and getting lost when driving a carriage. In the anime, this results in him staying at the Phantomhive manor to be trained by Sebastian, but his presence only serves to annoy and anger the entire Phantomhive household. Furthermore, whenever he messes something up, he has a tendency to overreact and attempts to commit suicide in a fit of melodramatic humiliation. During one of these attempts, Sebastian stops him and it is at this point that Grell's pre-existing admiration for him becomes a full-blown crush (but it turns out to be infatuation). Despite these constant attempts to end his life when he does something wrong, others only stop him to avoid the resulting large, bloody mess (Sebastian informs him that he can kill himself off the Phantomhive premises, indicating a lack of friendship between himself and other servants). He eventually does this so often that even the Phantomhive servants give up on trying to stop him, much to his surprise.
As a Shinigami, however, he is over-the-top and flamboyant, with a tendency to use female nouns and pronouns when referring to himself (called onee kotoba, "big sister speech", this is a common affectation of gay and MTF transgendered people in Japan.) He also has a tendency to put things in terms of theater, referring to Angelina's death as the falling of curtains on a theater act, and comparing his relationship with Sebastian to the famous play, Romeo and Juliet. He apparently has feelings for Sebastian, much to the latter's disgust, and gives Sebastian the nickname "Sebby" in the manga, "Sebasu-chan" and "Bassy" in the Japanese and English dub of the anime respectively. Despite his overwhelming love for Sebastian, he seems well aware that Sebastian hates him as shown in episode 10 of Kuroshitsuji II. During their "tea date" Grell was very frightened and kept mentioning that although it was what he had always wanted, it didn't feel right.
Although Grell realizes that Sebastian does not return his affections and even finds them distasteful, he is so smitten that he allows the demon to take repeated advantage of him, willingly trading his assistance for small favors (such as Sebastian striking handsome poses for his camera) even when that assistance results in injury or embarrassment. Apparently he feels that any attention from Sebastian is better than none.
However, his affections are not limited to Sebastian, as he seems to find men, in general, attractive. For example, with William Spears, while he calls him a sadist, he seems enamored by his eyes, saying they send chills up his spine. In Kuroshitsuji II, after seeing Undertaker's eyes, he inmediately says: "Hold me", indicating he finds him attractive. He also hunts down Pluto, saying he made his hunk radar go off. In particular, he seems to favor those he deems immoral.
Initially it would appear that the other Shinigami do not seem to be overly fond of him as William constantly refers to him as "trash", but the manga and musicals imply that only William has a problem with him as the other Shinigami respectfully call Grell "Senpai". Ronald Knox in particular is exceptionally fond of him, as Ronald always refers to him as "Senpai" and takes his advice on things over William's.
Grell's favorite color is red, as he is described as the Shinigami in red by Angelina, commits the Jack the Ripper murders so he can paint "ugly" women red with their blood, and says ordinary women are not fit to wear the color.He tells Angelina that he will join forces with her because of his empathy with her desire for a child; he too wishes to be able to give birth, he says, but is unable to since he is a man.
Grell has two distinct personalities. Most of the time he is cheerful, if somewhat sadistic, with a playful flirtatious quality, and is usually seen whining about William or flirting with Sebastian. However, at any given time, Grell can switch to a frightening and bloodthirsty persona who will do anything for the desired results. Apparently, he is apathetic to the fact that neither Will nor Sebastian have any interest in him, as shown in the third OVA when William stabbed him in the head twice, Grell didn't seem to care that there was blood running down his face, rather, he simply continued to flirt with both Will and Sebastian.
Grell initially appears as a meek man with long, brown hair tied back with a red ribbon, golden yellowish green eyes like most Shinigami, and round glasses. He dresses in simple, mostly brown clothes to match his seemingly shy personality. However, it is later revealed that this is not his true appearance, as he is actually a Shinigami. In his Shinigami form, he has long, red hair, golden yellowish green eyes, false eyelashes, shark-like teeth, and red-framed glasses, which are accessorized with a neck chain adorned with skulls. He also wears a suit like other Shinigami that includes gloves and a tie, high-heeled ankle boots, and a red coat he took from Angelina's corpse, which he slings off his shoulders and wears around his elbows. Occasionally, his tie is replaced with a red-striped bow. He is slender and 5'6" tall. In the forth OVA, as a young man, he is shown to have short red hair,similar to that of Ronald Knox in style, and wears a black suit, with a black tie, which seems to be the standard shinigami uniform,as most shinigami wear this, with exception of himself. He also wears trainee glasses, carries a small trainee death scythe.
When Madam Red (Angelina Durless) started the Jack the Ripper murders, he followed her around, as she was the reason his death list was so full. He reveals himself after one of the murders, and says he understands her feelings, because as a man, he cannot have children of his own. He agrees to help her, and takes up the disguise of her butler to avoid suspicion.