Pico VS Hank J. Wimbleton (Pico's School VS Madness Combat)

Okay this might be Pico's worst matchup but still
Connections:
-Both were originally from Newgrounds games
-Both came to popularity over the last couple of years thanks to Friday Night Funkin' and it's mods
-Both are extremely skilled in using guns
Battle Name: Pico's School of Combat

It's not that bad, Conker might also work.

Yeah, Pico VS Conker is pretty close imo

Especially since Pico and Conker both rule the world at some point and do drugs.

Plus I'm pretty sure they both excessively swear

for the current battle, I'm rooting for Pico, I might be a bit biased toward him but he's a lot younger and is still pretty smart, he also lives to be 113 years old, but Hank is super close.

Yeah I'm rooting for Pico and betting Hank
Hank does have a wider arsenal and has more combat experience I think
Plus he's bested Tricky the Clown several times and can come back after death