"Funny Aneurysm" Moment: After first releasing Tatanga, Herman Smirch is ordered to take him and Princess Daisy out to lunch. Where do they go to eat? The World Trade Center. As if that's not enough, when they get there, a dark cloud is hovering above the towers. Does This Remind You of Anything??
Oddly, the Twin Towers show up in the Super Mario Bros. movie—when Koopa starts merging the worlds, his run-down pair of skyscraper palaces merge into the WTC.
And in the second Game Boy story, Tatanga and his minions hijack a space shuttle. The shuttle's name? Colombia.
Jerkass Woobie: Herman Smirch in the Game Boy Comic stories, while he was initially depicted as a snivelling Dirty CowardJerk Ass. But by the 2nd story he gets a lot of Sanity Slippage and a Beard of Sorrow as he tries to maintain his sanity as he tries to evade Tatanga's forces in which over the course of the series he tries to evade Tatanga and his Army and the Police (especially considering the various crimes that the former forced him to do). The fact that Herman does occasionally do a Pet the Dog act with kids ever since the 2nd Game Boy story does help in this regard.
The Scrappy: Stanley the Talking Fish, at least as far as Mario and Wendy Koopa are concerned.