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.

Strawberry Shortcake

Strawberry Shortcake was riding back in 1982. This figure has an unusual smell that I don't really think smells like anything but other Strawberry Shortcake toys (and apparently lasts at least 30 years). This is the only figure I have come across of a person skating in a dress. Her enormous head/hat makes this figure fall over pretty easily (that would probably be a much bigger problem than the dress).

The Simpsons Pinball

This is the first attempt at a Simpsons pinball game. It came out in 1990 and features a number of images of Bart riding his skateboard. In addition to the backglass there are a few images of Bart with board on the playfield as well as a nice side graphic featuring Bart skating with a stack of hotdogs. Bart is shown as both goofy and regular. This is a pretty fun machine although I think the later Simpsons Pinball Party is a little better (which will be featured here at a later date). More info and images can be found at the Internet Pinball Database.

Roll-Along Smurf / Super Smurf

This smurf is rolling along on a pretty sweet pig. According to the smurf collecting site Bluebuddies, this is a promo variant with a skateboard shaped deck (as opposed to a leaf shaped deck) and fatter wheels. I'm can't quite track down a year for this guy but the leaf skateboard version is from 1978 (most companies seemed to go to the pig shape around '79-'80).

Edit: Looks like the pig shaped deck figure (Roll-Along Smurf) is from 1990.

Edit: Picked up the "Super Smurf" version with the leaf shaped deck. It not clear which side should be the nose and tail. Unlike the Roll-Along Smurf, the Super Smurf can be taken off the deck. I didn't notice this guy's unusual stance until looking at the side picture. His back foot is facing backwards similar to how a roller skater rides a bowl.

Dan

Dan were an English punk band from late '80s. They weren't known as a skate punk band but while going through their records recently I found two skateboard references. The first is from the inner label on their live LP, Kicking Ass at T.J.'s (Meantime Records 1989).  It features a pretty rad cat cruising with his hat flipped up and a brew in his hand. The second is from the insert in their third album, Mother with Child and Bunny! (Workers Playtime 1988). This dude is pulling an invert on a setup that looks like it has femurs for wheels while he thinks about a piece of piss.

Bamba

I found this snack while walking down the natural foods aisle in my local grocery store. It's made in Israel, where babies learn to skate while still in diapers. The snacks themselves taste like peanut flavored cheese puffs (which sounds gross but was actually pretty good).

Garfield II

Garfield is seen here rocking the ringer polo and headband in 1981. Unlike his last appearance, this time he opted for the classic cartoon shirt-and-no-pants look. He topped off the look with some knee pads. Judging from his tail position it looks like he is cruising pretty fast.

Spazz / Charles Bronson

For the second pressing of their split 7", Spazz and Charles Bronson swiped a pic of Neil Blender for the cover. He's riding a mini and the board looks like very late '80s or early '90s. The split itself came out in 1995 on 625 Thrashcore and is probably the greatest power violence split out there.