Billy is the OG TDD. He is also a boxer.
He is basically the Tech Deck mascot come to life. He is the finger riding the fingerboard in the Tech Deck logo.
Billy is the character with the most unique sculpts in the entire toyline. He has a record of seven sculpts.
He is the only Dude to have three sculpts in G1 -- the first generation of TDD (defined by not having any arms). Only two other characters ever had a second G1 sculpt produced: Stevie J and Petey.
Billy's first figure came out in Crew 2. Remember that numbers were not added until Crew 10, and they do not reflect the release order at all. Still, this was one of the earliest characters produced in their inaugural year of 2000. This figure has blue and white sneakers and a red backwards-turned ballcap (like the logo).
His second figure came out in Crew 9. He was dressed in a hoodie. This figure was produced in many colors including neon pink and neon orange in the Hot Feet series. The hoodie is supposed to resemble the robe that a boxer would wear upon entering the ring. Funny thing about that. Of all the armless (ergo handless) TDD, you can determine what they represent based on their attached accessory. I mean, Scott has a football, Larry has a basketball, and Homer has a baseball bat. But they decided to make Billy here a boxer. A boxer with no hands. Is he a kickboxer? What gives?
His third sculpt saw him come back as a generic logo dude with a backwards cap. This was in Crew 11. This time they printed "Tech Deck" on the hat. While a couple characters sport a "TD" in their design, this is the only figure made with Tech Deck spelled out. This figure has green, orange, yellow, and blue versions (but the yellow and blue versions lack the printing).
Billy's fourth sculpt was basically the last G1 figure produced, now with static arms. This is the definition of G2 -- figures have arms, but the arms cannot be bent or posed. This figure is exclusive to one of the RC boards of 2003. Here he has a red hat and blue sneakers.
His fifth figure is another G2 figure. Now he wears a yellow hardhat -- like one you would wear on a construction site. The hat has a magnet in it, which allows Billy to ride his skateboard upside down. This is the only TDD figure with a magnet in his head. It also reminds me of a 1980s Krazy Glue commercial where a dude puts glue on his hardhat and suspends himself from a metal beam. Billy could recreate this commercial with his magnetic hat. I think this figure is exclusive to the blue Magnetic Carry Case. However, I have never seen one new, so I cannot say for sure.
His sixth sculpt is the "boxer" sculpt from G1, now with arms that can bend. This is the defining feature of G3 -- bendable arms. So, hey, Billy now has arms (and hands) and boxing gloves. The figure finally looks complete and ready for a boxing match. This design has yellow, orange, red, purple, and green figures.
His seventh figure is a brand new G3 design that came out in 2005. Now he is a bare-knuckle boxer. The gloves are off! He has the bandages on his hands and a few cuts and scrapes on his head. I am not sure why they turned him into a bare-knuckle boxer specifically, but there were a couple famous boxing movies that came out around the same time as this figure: Million Dollar Baby (2004) and Cinderella Man (2005). Maybe this had some sort of influence on redesigning Billy. This figure has three versions: Brown outer shirt with light blue pants, white shirt with green pants, and red shirt with dark blue pants.
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