First Lieutenant Rip van Winkle is a character in the manga Hellsing and a member of the Millennium forces. One of Millennium's top soldiers and a member of the Werwolf special forces, van Winkle commands her troops to steal a VTOL carrier called the Eagle from the British which she subsequently renames the "Adler" (German for "eagle") and paints a swastika in blood on its main deck. Along with Zorin Blitz and Schrödinger, she briefly makes a cameo in a flashback during Hellsing III, and also during the ending credits. She makes her full appearance in OVA IV.
She is voiced by Maaya Sakamoto in the Japanese version of the anime and Kari Wahlgren in the English version, the latter of whom also voices Diva.
Rip uses a long-barreled flintlock musket that fires magic bullets which "punish all without distinction," tracking targets of their own accord, and which are seemingly armor-piercing (destroying helicopters, fighter jets and missiles with ease). These magic bullets are even able to change their trajectories in mid-flight and repeatedly pepper a target before expiring. She does not appear to have any other powers beyond this however. She also enjoys singing operas, especially Der Freischütz, and she often compares herself to the character Kaspar from that opera. The Major even notes that she is very much like Kaspar (and also likens Alucard to Zamiel, the antagonist of that opera and representative of the devil). Additionally similar bullets, that never miss their target, are used by Kaspar. The Major at one point tells Rip Van Winkle the end of Der Freschütz and says "First Lieutenant Rip Van Winkle, do you know how Der Freischütz ends? Kaspar, having trifled with the Black Huntsman Zamiel, is whisked away to hell for his sins. His corpse is then thrown into a ravine to be eaten by wolves. Prepare yourself, First Lieutenant, for now, Zamiel comes to collect you."
In several scenes she is also seen with an umbrella, which could be a reference to the practice of World War II German snipers to use umbrellas with camouflage foliage woven between the arms as light, adaptable and mobile personal camouflage. Alucard instills a great deal of fear in Rip as he approaches, and inevitably kills her, despite her last ditch effort to force him over the edge of the Eagle's deck with a magic bullet. Alucard stakes her through the chest just left of her heart with her own gun, after being repeatedly peppered by the bullet and then literally catching it in his mouth. He then drinks her blood in the climax to Volume 5 of the manga before using his shadows to devour her body, killing her and making her his familiar. The Major would not permit the Doctor to fry her through the chips, and in fact, in a rare gesture of "generosity," requests other members of Millennium to Heil her, bidding her "Auf Wiedersehen." ("Sayonara" in the Japanese version)
Her mission was to effectively trap Alucard on the Eagle because he cannot cross water without the aid of some form of external transport such as a plane or ship. By using the Eagle as a decoy, Millennium isolates Alucard in the middle of the ocean while the rest of Millennium makes its landing operation; to boost the morale of his army to a fever point, the Major glorifies Van Winkle's death (even promising her through the radio they would again meet in Valhalla) so hers will be the first death of the operation, thus priming the army for the destruction of London. Unfortunately for Millennium, Alucard takes control of the ship and manages to return to coastline, though the Major himself seems to be anticipating this.
Rip later shows up as a familiar after Alucard releases his zero restriction, merged with Tubalcain Alhambra. After helping shoot down Maxwell's helicopter and attacking Anderson, she is destroyed in a massive fire along with all the other familiars. This scene was not published in Young King OURs, but was added to volume 9. In the most recent chapter of The Dawn, Rip also makes an appearance as a young, farsighted soldier, encountering Alucard after his initial, rather comical fight with the Captain and while he was smoking with his coffin. She appears in full uniform, wearing her hair in two braided pigtails, and bears the rank of Untersturmführer. The glasses she wears (which are not actually hers, but were mixed up in the confusion) make it difficult for her to focus properly, and Alucard spends some time trying to make her understand who he is and why he's in the building. Finally, realizing that he is an enemy, Rip tries to shoot Alucard, but is knocked unconscious by his sentient coffin in an amusing way: being Judo chopped and kicked across the hall.
Since The Dawn is currently incomplete, it is often debated among fans that she was turned into a vampire and given magic bullets by Alucard himself. This would seem to explain why they were familiar with one another in volume 5, and it would also make the comparison to Der Freischütz that much more literal. However, it is unlikely Alucard was indeed her sire, seeing the immense difference in sheer battle power seen between Rip and Alucard's true fledging, the former policewoman Seras Victoria.