This is both funny and terrifying!
Spectacular Spider-Man (Vol. 1) #189
Published: c. April, 1992?
Cover Date: June, 1992
“The Osborn Legacy”
Writer: J.M. DeMatteis
Artist: Sal Buscema
Inker: Sal Buscema
Letterer: Joe Rosen
Colorist: Bob Sharen
It’s reasonable to consider that if J.M. Dematteis’ original idea for “Kraven’s Last Hunt” was first conceived as a Batman story, his take on Peter Parker vs. Harry Osborn felt like a Batman / Joker approach. This panel, due to a faux-Goblin armed with a real gun is totally Joker-ish.
But due to the background story of friendship both characters share behind their masks, the stakes of the fight raised way up high, because they are deeply personal.
And it’s even sadder to acknowledge that Peter’s own best friend had to succumb to madness by inheriting his Father’s.