Herr Logan
While awesome, the Spider-Man movie was riddled with bad decisions. I believe the next one will be, too. My solution probably wouldn't fly with a non-fan audience, but I have a vision anyway:
The first movie features Peter, his surrogate parents, J. Jonah Jameson (more screen time), Betty Brant (main love interest), Joe Robertson (cameo), Eddie Brock (cameo), Dr. Otto Octavius (main villain), Captain George Stacy, Norman and Harry Osborn (cameos), Mary Jane (cameo) Flash Thompson (as the character truly is) maybe a couple small-scale side villains and petty crooks briefly, and whoever else needs to be here. When I say "cameo", I mean it could be several scenes, but not integral to the main plot. Parker is witty, and Spider-Man is a smart-alecky, dynamic hero who bounces off the walls too fast for crooks to draw a bead on him. He has fun taking down robbers using moves he used in the comics. This is during high school. Betty is the lead love interest-- Peter's first girlfriend. Doc Ock had dealings with Betty in the comics and took her hostage a couple of times, so this should satisfy continuity buffs and nitpickers. Mary Jane is a peripheral love interest that a jealous Betty sees as threatening. The groundwork for the Osborns' characters could be started here, but not fully delved into yet. Brock has a peripheral part that has him hold resentment toward Spider-Man.Captain George Stacy will be killed during a battle between Doc Ock and Spidey-- it's Otto's fault, but Spidey takes heat anyway. By the end of the movie, Betty has broken up with Peter because he is too secretive and seems to crave danger in his work. Peter will NOT give the "friend" speech, he will just accept that he won't be able to have normal relationships while he wears the webs.
The second movie features everyone from the first, plus Gwen Stacy, Colonel John Jameson (cameo), more side villains and petty crooks, Dr. Connors (cameo), and whoever else sounds like a good idea. Jonah Jameson and Joe Robertson will have a bigger part, as will Harry Osborn, Mary Jane and Norman Osborn will be the main villains. Gwen blames Spider-Man for her father's death but falls in love with Peter. Mary Jane digs Spidey and Peter, but Peter loves Gwen. Harry dates Mary Jane but it doesn't work out. Love triangle with Peter, MJ and Gwen is dramatic but light-hearted and not sappy. Norman Osborn wears a decent costume and has actual criminal goals, runs afoul of Spider-Man and has a feud with him throughout the film. John Jameson mentions that he is going into space; Jonah is proud, loud, and cantankerous. When Norman learns that his son's roommate Peter is Spider-Man, he goes even more nuts and kidnaps Gwen. They do the bridge bit, and either Gwen dies, or they can wimp out and have her get saved. If she is saved, she will move away to England to live with Uncle Arthur (as she did briefly in the comics before her death... so don't think this is out of left field here), traumatized. Green Goblin dies by his own glider. Mary Jane comforts Peter, who is considering quitting the hero game. At the end, a super-villain (take your pick) shows up, causing mayhem, and Peter instinctively puts his mask on and gets into the action, ending on the note that, surprise, surprise, he ain't quitting.
Third movie features Venom as the big bad. The alien symbiote will come to Earth via John Jameson's return flight. I don't know, they did it in the cartoon, and it's the best way to do it quick without doing the Secret Wars. Anyway, Eddie Brock has fallen on more hard times, supposedly because of that accursed Spider-Man. The symbiote finds him somehow and they get their Venom groove on. Mary Jane is now the main love and she and Peter are together. I don't have much in mind for this one except lots of character drama, more character comedy, and a bad-ass Venom trying to tear Peter's life apart without attempting to reveal his identity to the public. At this point, all kinds of things could happen. Most of the good villains in Spider-Man came before Venom, so there are many to choose from as side plots and scenes.
This is my humble, too little, too late vision of a Spider-Man trilogy. It would never make it in the movies, partly due to the way stars are cast. You probably wouldn't have all the great actors who are just "perfect" for their parts making cameo appearances and peripheral plots in earlier movies in preparation for their spotlight in a future movie. Some might, if they were really nice and liked the movies, but it's not realistic. These people get better offers that would conflict.
I'd keep Dafoe as Goblin, Maguire as Spider-Man, and definitely, definitely J.K. Simmons as Jameson. Could he be any more awesome? Simmons is good at everything he does.
Let me know what you think of this. If you've been reading all this. If you have, go lie down. It's not good to look at the monitor for this long!!
The first movie features Peter, his surrogate parents, J. Jonah Jameson (more screen time), Betty Brant (main love interest), Joe Robertson (cameo), Eddie Brock (cameo), Dr. Otto Octavius (main villain), Captain George Stacy, Norman and Harry Osborn (cameos), Mary Jane (cameo) Flash Thompson (as the character truly is) maybe a couple small-scale side villains and petty crooks briefly, and whoever else needs to be here. When I say "cameo", I mean it could be several scenes, but not integral to the main plot. Parker is witty, and Spider-Man is a smart-alecky, dynamic hero who bounces off the walls too fast for crooks to draw a bead on him. He has fun taking down robbers using moves he used in the comics. This is during high school. Betty is the lead love interest-- Peter's first girlfriend. Doc Ock had dealings with Betty in the comics and took her hostage a couple of times, so this should satisfy continuity buffs and nitpickers. Mary Jane is a peripheral love interest that a jealous Betty sees as threatening. The groundwork for the Osborns' characters could be started here, but not fully delved into yet. Brock has a peripheral part that has him hold resentment toward Spider-Man.Captain George Stacy will be killed during a battle between Doc Ock and Spidey-- it's Otto's fault, but Spidey takes heat anyway. By the end of the movie, Betty has broken up with Peter because he is too secretive and seems to crave danger in his work. Peter will NOT give the "friend" speech, he will just accept that he won't be able to have normal relationships while he wears the webs.
The second movie features everyone from the first, plus Gwen Stacy, Colonel John Jameson (cameo), more side villains and petty crooks, Dr. Connors (cameo), and whoever else sounds like a good idea. Jonah Jameson and Joe Robertson will have a bigger part, as will Harry Osborn, Mary Jane and Norman Osborn will be the main villains. Gwen blames Spider-Man for her father's death but falls in love with Peter. Mary Jane digs Spidey and Peter, but Peter loves Gwen. Harry dates Mary Jane but it doesn't work out. Love triangle with Peter, MJ and Gwen is dramatic but light-hearted and not sappy. Norman Osborn wears a decent costume and has actual criminal goals, runs afoul of Spider-Man and has a feud with him throughout the film. John Jameson mentions that he is going into space; Jonah is proud, loud, and cantankerous. When Norman learns that his son's roommate Peter is Spider-Man, he goes even more nuts and kidnaps Gwen. They do the bridge bit, and either Gwen dies, or they can wimp out and have her get saved. If she is saved, she will move away to England to live with Uncle Arthur (as she did briefly in the comics before her death... so don't think this is out of left field here), traumatized. Green Goblin dies by his own glider. Mary Jane comforts Peter, who is considering quitting the hero game. At the end, a super-villain (take your pick) shows up, causing mayhem, and Peter instinctively puts his mask on and gets into the action, ending on the note that, surprise, surprise, he ain't quitting.
Third movie features Venom as the big bad. The alien symbiote will come to Earth via John Jameson's return flight. I don't know, they did it in the cartoon, and it's the best way to do it quick without doing the Secret Wars. Anyway, Eddie Brock has fallen on more hard times, supposedly because of that accursed Spider-Man. The symbiote finds him somehow and they get their Venom groove on. Mary Jane is now the main love and she and Peter are together. I don't have much in mind for this one except lots of character drama, more character comedy, and a bad-ass Venom trying to tear Peter's life apart without attempting to reveal his identity to the public. At this point, all kinds of things could happen. Most of the good villains in Spider-Man came before Venom, so there are many to choose from as side plots and scenes.
This is my humble, too little, too late vision of a Spider-Man trilogy. It would never make it in the movies, partly due to the way stars are cast. You probably wouldn't have all the great actors who are just "perfect" for their parts making cameo appearances and peripheral plots in earlier movies in preparation for their spotlight in a future movie. Some might, if they were really nice and liked the movies, but it's not realistic. These people get better offers that would conflict.
I'd keep Dafoe as Goblin, Maguire as Spider-Man, and definitely, definitely J.K. Simmons as Jameson. Could he be any more awesome? Simmons is good at everything he does.
Let me know what you think of this. If you've been reading all this. If you have, go lie down. It's not good to look at the monitor for this long!!