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.