Lily Hollister enjoyed a privileged childhood alongside her best friend Carlie Cooper. Lily's father, wealthy attorney Bill Hollister, became a father figure to Carlie. As adults, fun-loving Lily and workaholic Carlie became roommates. Lily met Harry Osborn while he was investigating potential political candidates in New York, including Bill Hollister. Bill was now a city councilman and Manhattan's district attorney. Lily and Harry soon became lovers and Harry spearheaded a million dollar exploratory committee regarding Hollister's potential as a mayoral candidate. Somewhat flighty in using her wealth, Lily found a kindred spirit in Harry, who impulsively bought the "Coffee Bean cafe" in an effort to impress her, while on a date. Shortly after the purchase of the Coffee Bean, mayoral candidate Lisa Parfrey was slain by a villainous person in a Grey Goblin disguise, and Lily, supported by the Deputy Mayor Wexler, convinced her father to enter the race for mayor.
As time passed, Lily grew increasingly skeptical of Harry's best friend Peter Parker's erratic behavior, unaware that his frequent disappearances stemmed from his tending to his Spider-Man activities. Her skepticism did not prevent her from flirting with Parker periodically; perhaps she was unaware that Carlie was romantically interested in Parker. After Menace attacked a Hollister political rally, Lily was interviewed on television and viciously taunted the villain. Later, while socializing at the Coffee Bean, Lily observed Harry's dark side during an intense argument between Harry and his father, Thunderbolts director Norman Osborn. Bill was left comatose following another confrontation with Menace, and the grieving Lily regretted her thoughtlessness.
When Norman Osborn and the Thunderbolts hunted the wall-crawling Spider-Man, Bullseye laid siege to the Coffee Bean, while Lily, Harry, and Peter were inside; they were able to escape, however, the cafe was left in complete ruins. Lily and Harry later went to Oscorp Industries, in New Jersey after the facility was destroyed during the battle between Spider-Man, Anti-Venom, and the Thunderbolts, in an attempt to retrieve a file that would help him clear his name. While Harry was feverishly looking for the file, Lily kissed Peter to distract him from opening the door to a secret room storing a cache of Norman Osborn’s weapons and secrets by removing Norman's book "The Rise and Fall of an Empire," from the bookcase that blocked the entrance.
Having no idea or inclination of the identity of the terrorist, who was terrorizing the campaign trails the Daily Bugle eventually dubbed the suspect as "Menace" (a moniker traditionally used by the tabloids former publisher J. Jonah Jameson to describe Spider-Man). Menace was first observed hijacking an armored car full of explosives, but was thwarted by the rookie superhero Jackpot , Menace then embarked on reign of terror across New York City, attacking Stark Labs and a police station, apparently to obtain more equipment. At a dockside gang hideout, which Menace acquired murdering its former occupants, Spider-Man and Menace fought once more, but menace overwhelmed the web-slinger and escaped.
Later in yet another battle the villainous Menace gave Spider-Man, a horrible beating that allowed the NYPD to apprehend him, for the "Spider-Tracer murders." Menace slipped into Hollister's campaign headquarters, where the villain was observed by Harry as it transformed into Lily. The stunned Harry Osborn could not believe his eyes, as he discovered that his girl friend was behind all the mayhem being caused throughout the city. She explained that her plan was to get her father elected Mayor, and possibly regain his love, which seemed to be directed in the direction of Carlie. Lily's plan was just days away from becoming reality, so she felt compelled to inform Harry, how she became the Menace and learned of most of his family secrets. Lily revealed that she had been reading his journal, which was nothing more than the whining of an unappreciative brat. Through the Journal, She was able to gain access into the secret room, where she hope to find something that would assist her into helping further her plans to get her father elected. However, she accidentally knocked over a vile possessing the Goblin serum, which absorbed into her skin, enhancing her strength and durability. This accident turned out to be just the thing she was looking for, it would not only get her father to throw his hat into the ring, but it would also propel him into office.