In Sam Raimi's Spider-Man films, Aunt May was played by Rosemary Harris as a housewife who is widowed by the events of the first film. She was the one who encouraged Peter the most throughout the films with her words of wisdom as Uncle Ben had done before his death, in the second movie even managing to make him try to return to his Spider-Man life after losing his powers.
In the 2002 film Spider-Man, Aunt May and Uncle Ben took care of their nephew, Peter Parker. After Uncle Ben (Cliff Robertson) was shot and killed by a carjacker, Peter and May shared their grief for Uncle Ben. Later, when Peter had moved into an apartment with his friend Harry Osborn, Aunt May visited them on Thanksgiving. She was not shy about reprimanding Harry's father Norman for his rude and boorish behavior. Shortly thereafter, when Norman (who had become the villainous Green Goblin), learned Spider-Man's identity, he attacked May at home while she was saying her prayers. May was terrified by the Goblin's demonic appearance, and was hospitalized after the Goblin injured her. May showed up at Norman Osborn's funeral alongside Peter, M.J. and Harry; soon after that, she and Peter visited Ben's grave located elsewhere in the cemetery.
In the sequel, Spider-Man 2 (2004), Aunt May continued to look after Peter, and had had financial difficulties since the death of her husband, forcing her to sell the house and live in a smaller apartment. Her opinion of Spider-Man was not high, claiming "the less we see of him, the better." However, when May's visit to the bank with Peter was interrupted by a robbery perpetrated by Otto Octavius, Octavius took her hostage and climbed the side of a skyscraper with her. She was in turn, rescued by Spider-Man (and in return, helps Spider-Man during the battle by hitting Octavius with her umbrella), and from that point believes that he was good. Later in the film, Peter's powers began to wane because of a subconscious desire to live a normal life, and he decided to give up his costumed persona; Aunt May made a speech which encouraged him to resume his heroic activities. She later expresses that she feels she caused Uncle Ben's death ("You wanted to take the subway, and he wanted to drive you. And if I had stopped him, we'd all be having tea together"), prompting Peter to admit that he caused the death by not stopping the killer. May is understandably stunned and sad, but later thanked Peter and told him that admitting the truth to her was a brave thing to do.
In Spider-Man 3 (2007), Peter told Aunt May that he was going to ask Mary Jane to marry him, after which the two embraced. May then told him that he needed to come up with a good way to initiate the proposal, and that he needed to put his wife before him, no matter what. She then related to Peter how Uncle Ben proposed to her, and that they would have been married for fifty years "this August", had Ben not been killed. She then took off her engagement ring and asked Peter to use it to propose to M.J. May was also present alongside Peter when Captain Stacy told them that Flint Marko, his uncle's "actual" killer, was on the run. She played a strong role in providing moral support to Peter, but nothing much was really done by her in the third movie, nor was she ever targeted by Spider-Man's foes as in the previous two movies.
Later, when Peter informed May about Sandman's apparent demise at the hands of Spider-Man (under the influence of an alien symbiote), she delivered another speech, which was more of a warning to Peter of the danger to oneself in seeking revenge. Peter was at first shocked at his aunt's reaction, for he expected Aunt May to be happy as Sandman was the one who killed Uncle Ben. Peter soon realized that this was not the case, and Aunt May said that Uncle Ben would never have wanted revenge. Much later, May talked to Peter in his apartment where Peter says that he's done terrible things (after separating from the symbiote suit that had caused him to hurt Mary Jane and Harry). He tried to return her ring to her, but Aunt May said that she knew that he would find a way to put it right, and gave it back. May later showed up at Harry Osborn's funeral at the end of the film.