J. Jonah Jameson
Peter Parker's boss at the Daily Bugle newspaper is tough to cast. The ideal actors for the role are two who have already played it; J.K. Simmons from Sam Raimi's trilogy and Ed Asner from the 90's animated series. However, Marvel will probably try to distance their Spider-Man from previous versions in as many ways as possible.
What makes Simmons and Asner great for the role is their ability to be simultaneously funny and a little intimidating while yelling just short of profanely at a teenager. That combination of humor and rage is the defining trait of J. Jonah Jameson. It's a combination that was seen in Harold, the father of the Weir clan (including Daley's character Sam) in Apatow's Freaks and Geeks. Harold was played by Joe Flaherty, best known for his work on iconic sketch show SCTV. Once you've seen Flaherty yell at his freak daughter and geek son about people who have died after cutting class it's not hard to imagine him shouting out a request for more pictures of Spider-Man.
Robbie Robertson
Robbie Robertson is a well-respected editor at the Daily Bugle. He's one of the few people willing to stand up to J. Jonah Jameson that he might actually listen to. He's a consistent ally to Peter Parker both in costume and in his civilian identity. Romany Malco seems a bit young for the part, but that apparently doesn't matter if Marisa Tomei can play the traditionally gray haired Aunt May. Malco starred in Apatow's 40 Year Old Virgin as one of several sexual mentors to Steve Carell's titular virgin. Surely a slightly older Malco could play a more traditional life coach role to a young superhero.
Betty Brant
Peter Parker's first major love interest was Betty Brant, who dropped out of high school to support her family by working as J. Jonah Jameson's secretary. I've always thought that high school student Peter dating someone who works full time was a little odd. It's not a big thing but I prefer to think of Betty as more of an older woman who Peter has a small crush on. SNL's Vanessa Bayer, who recently appeared in Apatow's Trainwreck radiates so much warmth, compassion, and humor that it's easy to see a dorky teenager being drawn to her.
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