055 Jack

Jack is a jack-o-lantern dude.

Carving pumpkins into jack-o-lanterns as Halloween decorations goes back to the 1830s.  The Headless Horseman (often depicted with a jack-o-lantern for a head) from the Washington Irving story "The Legend of Sleepy Hollow," goes back to the 1820s.

The G1 Jack has no arms (of course) and a little cape giving him that Headless Horseman vibe.

The G2 Jack is basically the G1 mold (with the feet leveled off), now with thin arms like those of a scarecrow (he still has no hands).  This version was available in blue, green, and purple.

The first G3 figure is the exact G2 figure, but he now has wires in the arms so they can be bent and posed.  This figure is gray and was available with the 2004 PC Game Bare Knuckle Grind: FreakTown. 

A second G3 figure was completely redesigned.  Jack now wears a striped sweater, no cape, and has a crow on his left shoulder.  His head has a built-in peg that makes it intentionally removable.  He can also hold his own head in one of his hands.  (Oh yeah, he now has hands.)  In addition to the color of the stripes on the sweater, the pumpkin-head color varies with this sculpt.  The head comes in orange, white, and black mottled with red. 

This version of Jack was given a zood.  In addition to the crow that is part of his mold, they gave him another crow.  His name is Brandon.  The name comes from Brandon Lee, who starred in the 1994 film, The Crow.  Brandon Lee actually died while filming this movie.  He was accidentally shot with a gun intended to be used as a prop.  Brandon was 28.  The film was still released and has become a cult classic.

A G4 Jack uses the G3 mold, but now has the copyright of Tech Deck's new owner, Spin Master. Plus now there are no magnets involved.  His sweater has a very distinct paint job reminiscent of another movie icon.  The red and green stripes now make him a bit of a Freddy Kruger homage.  Of course, Freddy is the dream-demon from the Nightmare on Elm Street franchise.  This Wes Craven slasher series goes back to 1984 and features nine movies (plus a TV show).

A second G4 figure uses the same Freddy-inspired design (minus the crow on his shoulder) and is part of the kinetic Trick Dudes. The eight characters in this series are made of hard plastic, come attached to their boards, and do silly "tricks." Jack does a trick called the "360 Shov-It."

As you can see, Jack is one of the most thoroughly represented dudes. He has been produced within all the generations.  One weird thing is that in the second series of trading cards, he is still drawn as his G1 figure.  The second series of cards came out in 2004 when TDD was well into their third generation of figures -- ones with bendable arms.  Jack had already been released a couple times as a figure with arms at this point, so not updating his artwork for the card series is just pure sloppiness.