"Dark Side of the Boob" is the eighth episode of the second season of Big Mouth. It is the eighteenth episode of the series overall. It premiered on October 5, 2018. It was written by Kelly Galuska and directed by Bryan Francis.
A school sleepover turns messy as Nick dishes on a makeout session and the Shame Wizard works his miserable magic on the whole class.
- Nick Birch
- Gina Alvarez
- Missy Foreman-Greenwald
- Andrew Glouberman
- Lola Skumpy
- Jessi Glaser
- Jay Bilzerian
- Coach Steve
- Shame Wizard
- Matthew MacDell
- Nathan Fillion
- Miss Benitez
- Barbara Glouberman (Mentioned)
- Jenna Bilzerian (Mentioned)
- Shannon Glaser (Mentioned)
- Greg Glaser (Mentioned)
- Monica Foreman-Greenwald (Voice Only in Present Day; On-Screen Cameo in Flashback)
- Nick touches Gina's boobs.
- Tyler breaks the fourth wall to tell you, (the viewer) that he thinks you're sexually attractive and that he wants to touch your boobs.
- Missy masturbates with a stuffed maggot named Wiggles.
- Missy has an American Girl doll named Maddie, whose backstory is that she was an African slave.
- Jay claims that he would not use a condom when having sex because "he's not a woman".
- The Shame Wizard collects Nazi dildos.
- DeVon has arthritis.
- Gina says that her mom bought her a Miranda San Francisco sleeping bag at the 99 cent store. This is the first time Gina mentioned her mom, who has never appeared in the show and apparently doesn't live with her, as the only parental guardian in her apartment is her grandmother, as seen in "The Shame Wizard".
- Devin made DeVon make out with her at least 20 times before she let him touch her boobs.
- The Shame Wizard breaks the fourth wall, urging the audience to continue watching the next episode to see how this episode's story wraps up.
- This episode starts with a flashback to "What Is It About Boobs?", where the boys first started perving out over Gina's boobs.
- Tyler still has his horn that he grew at the end of "Guy Town".
- Lola is still salty that Andrew dumped her in "Drug Buddies".
- Matthew is still trying to be nice after being told to stop acting mean and catty in "Guy Town".
- Coach Steve tells everyone that he had sex with Jenna in "Steve the Virgin".
- Jay mentions how he fucks his pillow, as seen in "Pillow Talk".
- The Shame Wizard brings up how Jessi broke up Sannon and Greg in "Drug Buddies".
- This episode directly leads into the next episode, which is "Smooch or Share".
- The title of the episode is a reference to the album "The Dark Side of the Moon" by Pink Floyd.
- Missy has an American Girl doll of a slave.
- Matthew says that Ms. Green from the M&M commercials is a cunt.
- Lola jokes about 9/11, calling Andrew "Osama Bin Rubbin'", which is a pun on Islamic Extremist, Osama Bin Laden.
- Gina's Miranda San Francisco sleeping bag is a nod to her voice actress Gina Rodriguez's role in the other Netflix animated tv show, Carmen Sandiego.
- The dubstep song that plays while the message is being sent to all the phones is the theme to "The Kroll Show" which starred show creator, Nick Kroll.
- Missy watches Lester Holt on NBC.
- Miss Benitez teaches the kids about the constellation The Sculptor and how it represents Pygmaleon from Greek mythology and how he sculpted a statue out of ivory.
- Coach Steve confuses Greek Mythology with Greek Yogurt and references to a 2014 commercial for Oikos Greek Yogurt, which featured John Stamos.
- Coach Steve references to the Stevie Wonder and Paul McCartney song, "Ebony and Ivory".
- The Shame Wizard has a mixtape of him singing "Take on Me" by Aha.