Aunt May

May Parker is Peter Parker's aunt and the husband and widow of the late Ben Parker. She is a major character in Marvel's Spider-Man franchise, playing a major role in Peter's life. So far, three versions of May have appeared in HISHE: a version from the Sam Raimi Spider-Man films (played by Rosemary Harris), a version from the Mark Webb The Amazing Spider-Man films (played by Sally Field), and a version from the Marvel Cinematic Universe (played by Marisa Tomei).

How Spider-Man 3 Should Have Ended
Raimiverse Aunt May listens to Raimiverse Peter discuss his plans to propose to Mary Jane Watson. May claims that Peter reminds him of Uncle Ben who makes bad choices and does more bad choices for the rest of his life.

How The Amazing Spider-Man Should Have Ended
Webb Aunt May makes a brief cameo in which she demands eggs from Webb Peter and Uncle Ben.

Alternate HISHE
Webb Aunt May is mentioned by Webb Spider-Man.

How Captain America: Civil War Should Have Ended
MCU Aunt May is alluded to in this HISHE, with MCU Spider-Man fearing that Tony Stark will date her and become his "dad-uncle."

5 Stages of Watching a Spider-Man Reboot
MCU Aunt May is mentioned in this skit, where Tim mentions it's good that May is young and helpful to the other person's dismay.

How Spider-Man: Homecoming Should Have Ended
MCU Aunt May appears in the end credits, stumbling upon MCU Spider-Man unmasking himself. She begins to say, "What the fu-?!", but is knocked out by Captain America as he exclaims, "Language!"

Appearances

 * How The Amazing Spider-Man Should Have Ended (Webb)
 * amazing spider man bonus (Webb, mentioned)
 * 5 stages of watching a spider man reboot (MCU, mentioned)
 * How Captain America: Civil War Should Have Ended (MCU, mentioned)
 * How Spider-Man 3 Should Have Ended (Raimiverse)
 * How Spider-Man: Homecoming Should Have Ended (MCU)
 * How Spider-Man 2 Should Have Ended (Raimiverse)
 * How Spider-Man: Far From Home Should Have Ended (MCU, deleted scene)
 * How Spider-Man Should Have Ended (Raimiverse)

Trivia

 * The Webb version of Aunt May is the only one to appear once, having appeared in the The Amazing Spider-Man HISHE, though she has been mentioned on occasion. In contrast, the Raimiverse and MCU incarnations have appeared more than once.