|Occupation:||vampire, serial killer|
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Penn was a devout Puritan who was sired by Angelus in 1786 and regarded him as his father and mentor. His first act after being sired was to kill his sister and parents, and he began to target religious families resembling his own, carving crosses into their cheeks. Eventually he found his way to Los Angeles. Due to the similarity with Angelus' obsession with religious victims, Angel's associates initially assumed that he had secretly lost his soul and was the killer. Once past this misunderstanding they began to track Penn down, while Penn was targeting detective Kate Lockley, intending to sire her and force Angel to stake her. In the course of this investigation Lockley learned that Angel was a vampire, and eventually staked Penn through Angel's body, fortunately missing his heart.
Although he only appeared in one episode, Penn is occasionally seen in fanfic. Initially this was very rare and mainly due to the back story shown for the character, which sheds light on the history of Angelus and Darla, but with the growing popularity of Jeremy Renner in other media and the Six Degrees of Jeremy Renner meme he is sometimes used in crossovers with the Marvel Cinematic Universe etc. He is often paired with Angelus.
- Sinful Salvation by little Alex (litalex) (2000); "Just exactly how devout a Puritan is Penn?" (Angelus/Penn)
- The End is The Beginning by madders (2012); "Hawkeye wasn't the only identity that the man best known as Clint Barton had used- (or how Clint Barton really started off life as the vampire Penn)." Avengers crossover.