"Prison Sex" is a song by American Rock band Tool. The song was released as their second single from their second major-label release Undertow. The song uses a modified drop-B tuning. The track features an "anti-climax" coda, in which memorable verses and choruses dissolve into an unrelated, quiet final section.

The video for "Prison Sex" was created with stop-motion animation techniques, and was directed by the band's guitarist Adam Jones (who had previous experience in art direction and animation, including work on the dinosaurs in Jurassic Park) and was edited by Ken Andrews. The video was removed from the MTV playlist due to its disturbing content. "Prison Sex" was also nominated for 1995's MTV Music Video Awards' Best Special Effects category.

The video primarily revolves around a battered white humanoid, robotic-like doll figure trapped in a room full of cabinets that contain other humanoids, such as a caterpillar with the main humanoid's face, a jar with a wasp inside, a robotic character with a little child's face that twists and turns, and a being made out of what looks like meat and feces. During various points in the video the main character is confronted by a larger black humanoid who causes the doll to go catatonic. While catatonic, the black figure molests the doll with a paintbrush. In the beginning of the video, the black figure severs the doll's legs (even though they still move by themselves) and hangs them out of reach of the doll. By the end of the video, the doll subjects itself to the abuse by painting itself. In the final shot, it is revealed that the doll was in its own cabinet the whole time when the black figure closes the cabinet door.

With the release of the 1994 single "Prison Sex" and its music video, directed and created by Adam Jones, MuchMusic called the band into question by deeming the video too graphic and offensive, later running an episode of its Too Much 4 Much series to discuss the video.

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