Chip & Dale

Chip & Dale make their debut appearance on BPA riding tandem in this 2002 Japan-only Happy Meal premium. When pushed down and let go they move forward while the nose rises.

 

Ollie

Ollie from Zuru Smashers series 1: Sport released in 2018. Ollie comes in 2 colorways - blue and purple. There is a 3rd "bad sports" colorway (gray/red) who is called "Sk8." Don't think they thought too hard about the names. These came in plastic soccer balls that you would "smash" open to get the figure (although the balls could be put back together).

Check the new "anthropomorphic skateboard" tag to check out other personified boards.

 

Lost Kitties

Scoops (red) & Prickle Paws (blue) from Lost Kitties series 1 released in 2018. These guys came with a variety of accesories as well as some Play-doh type stuff that I think was supposed to represent cat sand. Scoops, featuring the cone of shame, seemed to come with the skateboard often, but Prickle Paws is shown on the checklist riding a skateboard (below).

 

Dean

Dean from It Chapter 2. This figure is from the Funko Mystery Minis set released in 2019. There was also a Hot Topic exclusive version where his hood is pulled up.