Nitwitz

Nitwitz are a lesser version of Runts that turn up in quarter machines. The logo has different fruits taking part in various "extreme" activities, including a watermelon riding a skateboard.

Boo Boo

Boo Boo riding a skateboard with rev-up action from 1991. This was a McDonald's toy put out to promote the Yo Yogi! show which ran during the '91-'92 season. In the show Boo Boo is depicted as a a kid and instead of just a bow tie he wears some "hipper" clothes. Boo Boo's skateboard has some sort of exhaust coming off it so I guess it is supposed to have an engine. In reality it holds a motor that can be revved up (by pushing him forward). If you give him enough speed he will do a wheelie.  The top of his deck says "LAF 4," which, according to Wikipedia, was the agency Yogi and his gang work for in Yo Yogi! (LAF stands for Lost and Found).

Cookie Monster

Cookie Monster pushing hard, probably cruising down to the bakery. This figure has a surprisingly realistic pose (especially considering you rarely see Cookie Monster below the waist). He also has a proportional sized deck. I think he's riding those old non-reversible rat bones.

Edit: Found a source stating that this is part of set released by Shell gas stations in the mid-80s.

Chocolate Chip Charlie

Chocolate Chip Charlie looks kind of like a pie but I think he is supposed to be a pancake (or maybe a cookie). Charlie is an IHOP toy from 1996. He has Spongebob like sleeves (not connected to anything)  and matching shorts. He's also rocking an IHOP hat. He is kneeling down and grabbing his knee (I think the side of the deck is too far out for him to grab). The wheels on his deck don't spin but there are three wheels on the bottom that do. It looks like it should be a pull-back or rev-up toy (considering how much room there is under the deck for gears) but the bottom wheels are just free spinning.

The Smarties

The Smarties were a West German punk band who put out their debut album, Whole Buncha Weirdos, in 1986 on BYO. It contains multiple skate songs as well as a drawing called Youth on the back cover which features a skater doing a handstand.

RC Ripskate

The RC Ripskate is a remote controlled skater made by Matchbox in 1987. My friend picked this up at a yard sale and it no longer had its remote so I do not know if it still works. He's doing a pretty serious squat; I don't think I ever seen anyone skate in such an awkward position. His head and arms are movable but I don't think that is controlled by the remote. The board itself is probably about as tall as he is if he were standing so I guess he's a longboarder. He's fully padded up (including fingerless gloves) and rocking the Flyaway helmet. He's also got a Tracker clown shirt (although he doesn't really have any trucks on his set up). This takes 8 AA batteries and 1 9-volt.

Spongebob Squarepants

This Spongebob was a General Mills cereal prize in 2011. I assume he is riding goofy and grabbing his tail but he could also be regular and in the middle of a backside layback. Since he is not wearing his air helmet it is safe to assume that Spongebob is looking for some undrained pools.