The Simpsons Arcade Game

Bart and Marge have great range and Bart seems to be the perfect melee character so I recommend these two to be your last two characters needed for completion. Your first playthrough should be either Homer or Lisa, they have very short range and aren't good characters, especially Lisa since she randomly catches herself on her jump rope leaving you open for attack. Your first playthrough should be just an ordinary playthrough, getting most of the trophies in one go. Your 2nd playthrough will be the speed run, 3rd will be on expert and 4th will be whenever you wish as by now this trophy should be the last thing you need. Take note that getting a GAME OVER, which means losing all of your continues then dying will NULLIFY the playthrough. Meaning that if you beat the game with that character, it won't count, at all. Play on the Japanese ROM on easy if you want, it'll work fine for the trophy.

If you do this locally with 4 people, then it will unlock the trophy at the end in one playthrough.

Single player method:

Using the button trick can get you the trophy if you have two controllers. Use controller 1 to select two characters and use the 2nd controller to select 2 characters, move the 4 characters up by doing team attacks. Bart/Lisa and Homer/Marge should be doing the team attacks together since it moves them both up and they hit everything whilst doing so.