Oakley attended The Kubert School in Dover, New Jersey for a year, intending to be a comics artist. However, his experience at the school convinced him that he couldn't handle the workload of a comic book artist and, still desiring to work in the comics field, decided to do lettering instead. In July 1986 he started on staff at Marvel, working under Jim Novak. For Marvel, Oakley lettered Avengers for a long time, Avengers West Coast, the X-Men, the Fantastic Four during Walt Simonson’s run, Rampaging Hulk, and Amazing Spider-Man. Oakley concluded a late 1987 interview by remarking "I would hope, by this time next year, that I would have enough work that I could go freelance. I wouldn't mind the idea of working at home. That kind of appeals to me, not having to get up at 6:00 every morning to commute here. That I definitely would look forward to." Oakley indeed went freelance by the end of 1988. For DC, he worked on a number of the Superman titles, Batman, Lobo, DC vs. Marvel Comics, Batman: Gotham Knights, Justice Society, and Hawkman.
Death
Due to the fact that he did not possess medical insurance, he was forced to letter comics from his hospital bed to pay bills before he died of cancer in Utica, New York. His hometown was Oneonta, New York. Oakley was survived by his wife Leslie and son Stephen. He was halfway through designing at the time of his death. The final volume was dedicated to his memory, with Moore noting in the introduction to the book that he felt the cancer made Oakley's lettering style much better than a non-cancer-addled letterer.
Lettering style
Oakley had a distinctive but understated lettering style. One of his trademarks as a letterer was to often erase or omit panel borders when they touched the top, side, or bottom of a word balloon or caption, thus opening up the balloon/caption to the gutter. In this regard, Oakley's lettering style was similar to John Workman's. Also like Workman, even in the age of computer lettering, Oakley did all this lettering by hand, using a Hunt 107 pen. Before the age of computer lettering, unlike Jim Novak and others, Oakley was one of the few letterers to continue to create word balloons entirely freehand instead of using templates.
