Julius Jr.

Julius Jr. figure and skateboard from the Rock 'n Playhouse playset. The set was released in 2013 and also came with a quarterpipe.

Grimace II

Grimace skating from 1990. This is from Japanese exclusive happy meal set, translated to "Fun Time on Wheels." Grimace was the only skateboarder. The set featured McDonaldland figures on the 1988 Garfield set vehicles.

Grimace's previous appearance.

Max Mayfield

Max from Stranger Things, Funko Pop figure from 2018.

Skateboarder Smurf II

This skateboarder Smurf is from a 2009 extreme sports pack. 

Previous Smurf appearances: Skateboarder Smurf, Roll-Along Smurf, Surfin' Smurfs, Invert Smurf, Smurf Mug, Smurfette pin, Smurfette figure, and Handstand Smurf pin.