Jumbo Eraser

Just a jumbo sized eraser shaped like a skateboard.

Adventure Time

A dude from the inside cover of an Adventure Time book. If you slept on this show you blew it.

Bugs Bunny Nite Lite

Bugs Bunny in nite lite form from 1994. The bulb in this is almost unbelievable weak. Glow-in-the-dark figures are brighter. Anywho, Bugs is wearing shades in case I can figure out how to get an LED light in there.

Skateboard Smack-Ups

Skateboard Smack-Ups were a Garbage Pail Kid inspired line of figures from 1986. Since they depict children being seriously injured it's no surprise that these were banned and removed from shelves.

Skateboarder Smurf

Skateboarder Smurf from a 1998 McDonald's Happy Meal.

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

Spud

Spud is a scarecrow on Bob the Builder. His skateboarding adventures are chronicled in the 2001 episode "Skateboard Spud." Can't find a date for this dude but obviously 2001 or later. 

Michelangelo

The Teenage Mutant Ninja Turtles have made remarkably few appearances so far (just a bandana). Here's the first figure - Michelangelo from Burger King in 2003 - most likely a tie-in to the 2nd animated series which lasted from 2003 - 2009.

Mr. Potato Head

Mr. Potato Head's debut on BPA comes in the form of this 1998 figure from Burger King. He came with a launcher as well as a launch ramp and landing ramp. This is the same ramp/launcher/skateboard as the Woody Woodpecker figure also from Burger King.

Gumby III

Gumby's 3rd appearance on BPA. This figure and skateboard are from a playset including a jeep, a boombox, Prickle (the yellow dinosaur), and a 3.5" floppy disk digital coloring book. The set is from 1995 and ties into Nickelodeon's airing of Gumby reruns.

Universal Monsters

This line of Universal Monsters, from Little Big Heads, came out in 1999. I have no explanation why only the Mummy is wearing protective gear. I would've liked to see the Bride of Frankenstein included here.

Tony the Tiger II

Tony the Tiger appears in pin form from 1994. His previous appearance was as a set of 4 monochrome figures.

Snoopy IX

Snoopy is the undisputed king of licensing, this being his 9th solo appearance (not to mention 2 appearances in Peanuts sets). This half-3d magnet with a flat back which I actually can't find to check if there is a date on the back (he'd normally be on my fridge but the magnet fell out and I haven't glued one back in yet).

Other previous Snoopy appearances on BPA: Snoopy on a Green Board, Snoopy on a Green Board Again, Snoopy Mug, Wind-up Snoopy, Work Out Snoopy, Fatigues Snoopy, Poochiefied Snoopy, The Easter Beagle, Peanuts Skate N Surf set, & Peanuts Mini Skateboard set.

Smurf Pin

A variety of Smurf items have appeared on BPA, and this isn't even the first pin. A generic Smurf is seen here doing a handstand on a board that is going fast enough to kick up a cloud of smoke. Pretty impressive. Previous Smurf appearances: Roll-Along Smurf, Surfin' Smurfs, Invert Smurf, Smurf Mug, Smurfette pin, and Smurfette figure. This puts the Smurfs 1 back from Snoopy in number of appearances (and tied with Garfield).

Fred Shred

Fred Shred is made by Sprig Toys and is made of "sprigwood" (recycled wood & plastic). He came with a skateboard, snowboard, and a surfboard (that looks a little more like a skimboard or wakeboard). He's part of a larger set of people all shaped the same that come with a variety of accessories.

Elmo II

Elmo returns to BPA and this time has figured out decent foot placement. This Elmo is a giant compared to his first appearance. He has a button on his chest which makes him speak but it no longer works on this figure so I don't know what he said. He was part of a "Playtime Talker" series from 2000. He comes with a removable bike-style helmet that says "SKATE" on the side. This is the 5th Sesame Street post, after the aforementioned first Elmo appearance, Snuffy & Alice, Rosita, and a Honker. You can also hit the Muppet tag to see all the Muppet related skaters.

Super Bat

The Super Bat on his flying skateboard was advertised to "protect you from all evil, villains, and bad guys!" This dude is from 1966, making him one of the oldest toys seen here on BPA. He's kind of a gummy material that is also just sticky enough to get covered in dust and hair (these are sometimes referred to as a jigglers). I think he also came with a cape. The back of the packaging (which I don't have) gives a few tricks:

A. Boss or Wheelie - his normal position

B. Fly-Away - a manual

C. Hot-Dogger - just looking up while skating

D. Head Dip - looking down while skating

E. Kamikaze - a nose manual

F. Butt Breaker - looking up again but I guess a little more than the hot-dogger. It warns that nobody but Kabunga can do this but offers no further explanation about who this Kabunga is.

Dewey Duck II

Dewey Duck riding a board from a 1988 Kinder surprise set entitled "Donald and His Friends." There is a rarer version with blue hat and board that is Huey. This is the 2nd time Dewey has appeared solo in addition to the set of all 3 nephews skating.

Edd

Edd AKA Double D from Ed, Edd n Eddy, seen here as a Subway promo toy from 2003. This is a show I never watched, so this entry lacks the deep insight you've come to expect here at BPA.

Baby Pluto

Baby Pluto on a board. This is Pluto's first appearance on BPA, and possibly his only. This is from a series of "baby transportation" pins released in Japan in 2002. 

Peace Alien

Another vending machine alien, this time one who comes in peace. I believe this guy comes in 8 colors - green, gold, bronze, silver, blue/gray, red, magenta, and blue. I don't know what year these dudes is from but clearly inspired by mid-90s wheel sizes. Previous aliens include Russ Berrie alien, hip hop aliens, green alien and rainbow aliens.

Skater Bean

This is the 3rd Mighty Beanz bean to be featured on BPA, but the first from the original Australian series from 2002. He's got a real early 00s pop-punk look going on that I am not feeling. I do like his 2-tone deck reminiscent of some late 80s Alva stains. The other beans are Xtreme Skater Bean & Skateboard Bean.

Mr. Cool

Mr. Cool from the Mr. Men and Little Miss books. He was a Happy Meal toy from 2004 released in Europe and Australia.

Black Puffle

This is a Black Puffle from Club Penguin, a multiplayer online game of which I have no knowledge. This dude is from 2010 (I think) and originally came with a house and mini ramp.

Bugs Bunny III

Now this is a rabbit that knows how to chill hard. Bugs Bunny's third appearance finds him not so much riding coffin as hammock. Previous appearances include Bugs on a rocket skateboard and poser Bugs.