The game's premise is centered on the eponymous character, an anthropomorphic talking pencil who must gather the scattered segments of the totem pole that brought him to life.

In these levels, Woody must navigate through a maze, collect sketches and extra lives, and reach the end within a limited time.

[1] Dusty, an adventurer, returns to his office with a miniature totem pole consisting of six heads, and is immediately called to a rescue mission in Sumatra.

As a result, he misses a message from an anthropologist on his answering machine explaining that "on the third Wednesday of July under a full moon during a snowfall", the totem pole's power would be released; its segments scatter and create parallel universes for themselves, which threatens to destroy the world.

The bottom segment, Low Man, brings one of Dusty's pencils to life as a means to recover the scattered totem pieces.

[7] Lanford hid an easter egg within the second act of the game's first level that would render a mermaid – one of many beings created from the sketch mechanic – topless if four hidden items are collected in a certain order.

A reviewer for VideoGames noted the high amount of erasable elements and described the music as "lots of wacky toe-tappers", but found the visuals to be "a little grainy".

[17] The four reviewers of Electronic Gaming Monthly agreed that the ability to draw up necessary items is interesting, but that the controls make erasing enemies difficult and there are frequent cheap hits.

[8] Wild Woody failed to make a commercial impact, which Lanford attributed to its late release in the 16-bit era, questionable character design and standard platforming gameplay.

The writer particularly criticized the "awful" cutscenes and inconsistent controls which resulted in "unavoidable" damage from enemies, but acknowledged the music's high quality.

[19][20] Evan Hopkins of Screen Rant felt that the game's "eye-searing" cutscenes, "x-treme" attitude and obnoxious mascot character made Wild Woody "a perfect allegory for the failure of the Sega CD".