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Not Cool is a 2014 romantic comedy film directed by and starring Shane Dawson.

In Pittsburgh, Pennsylvania, a group of high school friends reunite during a Thanksgiving break from their college classes. Former prom king and college freshman Scott, played by Dawson, is dumped by his eccentric, hyperactive girlfriend Heather, and strikes an unlikely friendship with Tori (Cherami Leigh), a misanthropic, pessimistic former bullying victim who was initially cold towards him. Though as the two warm up to each other and embark on some wacky antics, their relationship starts to turn into something deeper.

The process of this movie being made was documented on the Set Behind the Scenes Reality Show The Chair (2014) on Starz, about Shane Dawson as the YouTube star in competition with traditionally trained filmmaker Anna Martemucci to both make a movie from the same script (her version being the much more artistic Hollidaysburg).

A great deal of controversy ensued from the nearly unanimous critical rejection of the movie, including executive producer Zachary Quinto removing his name from the credits, which did nothing to stop Dawson's existing YouTube audience from overwhelmingly voting him in as the winner of the contest.

This movie provides examples of:

  • Abhorrent Admirer: Heather, so much so that the pathos we're supposed to get from her dumping Scott is nonexistent.
  • The Ace: Marissa. She's blind because Shane Dawson thought it would be funny to have Tori's sister be so much more successful than her while also having a major disability.
    • Handicapped Badass: Marissa's disability is somehow no obstacle to her becoming an award-winning painter, getting a driver's license, or being the best player of Dance Central in the family.
    • Scott is also supposed to be this — the most popular guy in his class whom everyone thinks of as a brilliant artist — but the way Shane Dawson plays him makes this come off as an Informed Ability.
  • Actor Allusion: Aside from the fact that Scott, despite attempts to make him a distinct character, pretty much just is Shane Dawson in a teen comedy, Dawson added character beats taken from his real life, like Scott confessing to having an eating disorder, or the ending having him finally shave off his signature emo hairstyle (the significance of this being lost to anyone who wasn't one of his YouTube fans).
  • All Women Are Lustful:
    • Taken to ridiculous degrees even for a teen sex comedy. Apparently even Tori, despite being a lonely wallflower back in high school, spent all that time compulsively masturbating with vegetables.
    • This joke goes even more up to eleven with Tori's mom hitting on her daughters' love interests right in front of them and her own husband.
  • Alpha Bitch: Heather, Scott's ex-girlfriend, has shades of being one. Though she is really more downright insane than bitchy.
    • Shane also crossdresses as a high school Alpha Bitch in this movie.
  • Amazingly Embarrassing Parents: Tori's parents, whom the film introduces us showing Tori's mom shitting her pants while trying to do aerobics.
  • Ambiguously Brown: Latina actress Michelle Veintimilla is cast as Janie, the sister of Shane Dawson's very white character Scott. (They weren't related in the original script but became brother and sister after Shane's rewrites.) This by itself wouldn't be that big a deal, except the movie calls attention to it with a Running Gag of people trying to guess what ethnicity she is ("Ecuadorian", "Native American", etc.)
  • Author Avatar: Despite his best efforts, everyone who's seen this movie sees Shane Dawson's character of Scott as this.
  • Background Music: Lampshaded. Tori snarks "Cue The CW soundtrack" during an emotional moment when, indeed, the actual soundtrack of the movie is playing sappy background music, one of the movie's many moments of Bathos.
  • Beautiful All Along: The whole point of Tori's character is this cliché — she was bullied for her acne all through her teen years and became attractive and popular in college.
  • Beta Couple: Joel (Drew Monson) and Scott's sister Janie (Michelle Veintimilla).
  • Biting-the-Hand Humor: Shane Dawson throws in a jab at executive producer of The Chair Zachary Quinto with the line "Holy Zachary Quinto's eyebrows!" earlier in the film. Harsher in Hindsight after Quinto publicly disavowed the film and removed his EP credit from it.
  • Blind Mistake: Marissa's disability is constantly Played for Laughs while she's onscreen.
  • Blonde, Brunette, Redhead: The three major female characters in this movie, Heather (blonde), Janie (dark-haired) and Tori (auburn-haired) fit this trope. (Alternatively, Marissa as the blonde.)
  • Broad Strokes: The premise of the competition in The Chair was that both this film and Anna Martemucci's had to be based on the existing screenplay How Soon Is Now, keeping the broad plot outline, the names of the main characters and the setting of Pittsburgh. Very, very little of the original script survives in Dawson's film, which jumps genres completely from "coming-of-age dramedy" to "sex comedy romp", to the point of Canon Defilement in some cases (like turning Heather from a sympathetic character struggling with her identity to a caricatured Psycho Ex-Girlfriend). That said, the opening of the movie involving Heather dumping Scott in the middle of a sex scene was directly from the original script.
  • Butt-Monkey: Joel, matching the role Drew Monson played in Shane's YouTube videos of always getting his balls busted and mocked for being an awkward virgin.
  • Cain and Abel: Tori can't stand her Always Someone Better older sister Marissa, who starts off her Black Friday weekend by excitedly announcing she's engaged.
  • The Cameo: Kurt Angle shows up as a security guard. (This moment is a bit of a payoff if you've seen The Chair and Shane rejecting every actor who auditions for this ten-second-long part because they're not intimidating enough.)
  • Camera Fiend: Scott, who claims that he took the humiliating prom photo of Tori getting dumped that almost ruined her life simply because it was such an "artistic composition".
  • Camp Gay: Gil, Marissa's fiancé, is this stereotype — a joke about her being "blind" to his sexuality — although the joke then ends up not being about him being into guys but being into her mom.
  • Camp Straight: Both Shane Dawson as Scott and Drew Monson as Joel come off this way, reflecting their real-life YouTube personas (this film was made a year before Shane came out as bi). The fact that Scott is supposed to be a sensitive, emo-haired artistic guy who doesn't even know how many points are scored in a touchdown makes it kind of hard to believe a Pittsburgh high school voted him the prom king.
  • Cloudcuckoolander: Aunt Flo is an extremely grating, over-the-top version of this stereotype.
  • Comedic Sociopathy: Every single main character indulges in this. It's one of the main reasons Scott's third-act epiphany that he's a bad person falls flat — he's hardly more of a dick than "I-hate-everything-and-everyone" Tori.
  • Crazy Homeless People: The movie makes a running gag of a crazy black homeless man doing something disgusting in public for no reason.
  • Creator Cameo: A memorable sequence from The Chair shows that producer Corey Moosa serves as a "stunt double" for Shane Dawson's butt when he's mooning the city through the window of the Incline ride.
  • Cross-Cast Role: Shane Dawson playing an Alpha Bitch and a middle-aged female bus driver.
  • Crossdresser: Aside from the above examples under Cross-Cast Role, we also have Joel making Tori help him try on dresses to decide which one to buy for Janie.
  • Dance Party Ending: The movie ends with Scott and Tori doing their choreographed dance from the Dance Central scene at one last Wild Teen Party at the Vinyl Vault.
  • Delayed Reaction:
    Joel: Text me!
    Tori: Suck a dick!
    Joel: (awkward Beat) No!
  • Did Not Get the Girl: Joel — Janie decides she and Joel are Better as Friends and gets him laid with her slutty Girl Posse instead.
  • Disabled in the Adaptation: Shane Dawson made Marissa blind when turning the screenplay of How Soon Is Now into Not Cool, for no other reason than that it was "funnier".
  • Double Standard Rape: Female on Male: In-Universe example, as Tori initially doesn't believe Scott when he says that Heather forced herself on him. (Also an Out-of-Universe example, as many people pointed out even Shane Dawson would've hesitated before putting in as many jokes about this scene if it happened to a woman instead.)
  • The Eeyore: Tori, the main character, is bitter from her high school years, Hates Everyone Equally including her own family, and is a relentless Deadpan Snarker. Though she does start to find happiness when she finds a liking towards Scott, she still keeps her bitter, sarcastic tendencies.
  • Expy: A couple of characters are clearly identifiable for viewers of Shane's videos — Shane's "popular girl" cameo character he plays in drag is basically the same as his "Amy" character from YouTube, and "Aunt Flo" is essentially his "Aunt Hilda" character, only not played by Shane himself this time (since she has to interact with his character Scott).
  • Fake High: The "pot brownie" Tori feeds Scott turns out to just be a regular one.
  • Fan Disservice: A closeup of Shane Dawson wearing prosthetic breasts as "Mandy" toward the end of the film, followed by graphically showing Shane as Mandy and Drew as Joel making out.
  • Fantastic Drug: There's a Running Gag about different women's names being new slang terms for ecstasy ("molly") mixed with different substances: "ethel" is molly mixed with prescription drugs stolen from your grandparents, "maria" is molly mixed with hot peppers or other spices, and "rihanna" is molly mixed with steroids and adrenaline.
  • Fictional Social Network: Mostly averted, in order to appeal to Shane Dawson's Internet-savvy audience — as discussed heatedly in The Chair, when Shane's producer Lauren brought up the idea of using a Bland-Name Product for "Facebook" to avoid legal issues. Facebook is named — and shown — as is Joel having a Tumblr where he recounts his sexual exploits and Janie having a Pinterest where she names her interests and her dream purchases. However, in the opening scene where everyone is posting on Twitter, the actual Twitter icon is replaced by a fictionalized Ugly Cute version of it.
  • Flyover Country: The film was partially funded by a grant from the City of Pittsburgh, and takes place in the city, although there are few direct references to the setting other than a couple scenes at local landmarks like the Incline and Heinz Field. Scott has extremely mixed feelings about having finally "escaped" his past and achieved his dream of going to school in New York, only for it not to turn out the way he wished.
  • The Friend Nobody Likes: Joel, whose only actual friend is Tori because they were both social rejects in high school and is only cordial with Janey and Scott because he works for their dad.
  • Girl Posse: "Mandy, Stacy and Lacy", Janie's shallow friends she doesn't like much (one of whom is played by Shane Dawson).
  • Glory Days: The point of Scott's character, although we really aren't shown enough about his high school past to justify it.
  • High-Pressure Blood: An anatomically unlikely pulsating stream of arterial blood spurts out from Scott's earlobe the moment he gives in to Tori's nagging to overcome his fear of getting his ears pierced.
  • How We Got Here: Part of the much-criticized muddled structure of this movie is starting with a Wild Teen Party where Tori gets vomited on, before jumping back in time to show her coming home from college earlier that day, and then catching up to the party again relatively quickly.
  • Hypocritical Humor: This movie repeatedly describes a joke as offensive and problematic while in the process of making it, a tired device for a "Just Joking" Justification extremely familiar to viewers of Shane and other YouTubers — Heather screams "THERE'S NOTHING FUNNY ABOUT MENTAL ILLNESS" when other people refer to her as a "psycho", and Scott describes the Indian accent she puts on after stealing Shareef's mom's sari as "really racist" (even though Scott is conspicuously played by Shane, who wrote this joke).
  • Important Haircut: The ending of the movie, which comes off as serious Narm to anyone not familiar with how Shane's fans loved his signature hair.
  • Improv: Almost all the development of Joel's character came from Drew Monson doing this, including the involved sight gag of Joel trying and failing to mime cunnilingus.
  • Informed Attractiveness: Scott. Tori's rant to him (just before they have sex) about how she hates that he's so effortlessly attractive and effortlessly confident in his attractiveness comes across as major Character Shilling. (However you personally feel about Shane Dawson's appearance, his emo-teen affect absolutely does not come across as disarming, effortless self-esteem.) But see Informed Flaw.
  • Informed Attribute:
    • The middle act of the movie revolves around Tori trying to get Scott to "loosen up" because he's too "uptight" and "regimented", even though he hasn't had a chance to display these traits at all in the movie up to this point.
    • Apparently Tori's appearance is so different now that her acne is cleared up that none of her high school classmates even recognize her (which, judging just from the photo we're shown of "high school Tori" as Cherami Leigh with pimples on her face, is a stretch).
  • Informed Flaw: Tori and Janey calling Scott a self-absorbed asshole after the Second-Act Breakup falls just as flat as the Character Shilling he was getting previously, since while he has a shitty attitude and makes shitty remarks, so does everyone else in this movie, and he doesn't really do anything in the movie itself to earn this reputation (he mostly just passively reacts to things other people do).
  • Jabba Table Manners: A running gag with Scott is his habit of sloppily stuffing his face, which escalates from him eating a pizza on the couch to scarfing down fries while on his "drug trip" to messily eating an entire Thanksgiving turkey after his Second-Act Breakup.
  • Lost Aesop: The opening shot with people making dishonest/self-serving tweets and Tori's ending narration are Book Ends giving the movie a Social Media Is Bad Aesop, which is odd considering nothing about the movie in between has anything to do with this.
  • Lovable Sex Maniac: Joel. How lovable it actually is is debatable.
  • Meet Cute: Scott getting hit by Tori's car (one of the plot points from the screenplay in The Chair that both films kept).
  • Missing Mom: We suddenly learn during the conversation at Heinz Field that Scott's mom died of cancer, and he refuses to talk about it.
  • Mood Whiplash: The sudden attempt by this movie to become a heartfelt drama at the gymnasium scene, after everything else it's just made us watch, is dizzyingly abrupt.
  • My Girl Is a Slut: Scott is nothing but proud and astonished that "Tori the Whorie" is now actually living up to her name, including having a huge stash of condoms in the glove compartment of her car.
  • New-Age Retro Hippie: Joel and Janey's dad.
  • Nobody Touches the Hair: A Running Gag about Scott (and an in-joke about Shane Dawson's hair in real life) leading up to the big climax where he shaves it.
  • The Oner: The Wild Teen Party at the beginning.
  • Pillow Pregnancy: The infamous watermelon scene.
  • Pimped-Out Dress: The dress Joel buys for Janie that he found on her Pinterest pinboard.
  • Product Placement: American Eagle Outfitters gave this movie access to one of their stores to film the Black Friday scene and provided a lot of the costume pieces for it. There's also a scene prominently featuring the game Dance Central.
  • Psycho Ex-Girlfriend: Heather.
  • Raging Stiffie: The climax of the film features Joel about to get laid at a party only for it to be broken up by Shareef's parents coming home, leading to him looking down at his own bulging underwear and saying "Sorry, buddy".
  • Rape as Comedy: This movie has a lot of it, starting with Shane in drag as a high school girl complaining that the party they're at is so dull she hasn't been "roofied and fingered" yet, then going on to revealing that Janie's history teacher Mr. Draper is nicknamed "The Raper" because of his Covert Pervert tendencies to his female students, then having Tori crack a joke to a checkout cashier that her pregnancy was due to rape in the infamous watermelon scene, then culminating in an actual graphic scene of Scott being raped by Heather that the movie tries to get away with because of Double Standard Rape: Female on Male. (This scene includes Scott loudly protesting "It was RAPE!" only for Tori not to believe him, the resulting awkward silence being Played for Laughs, and party host Shareef morosely updating his "Number of Rapes at This Party" sign from 0 to 1.) More than anything else, it was this brand of humor that led competing filmmaker Anna Martemucci from The Chair (2014) — who is a survivor of sexual assault herself — to loudly denounce Shane and his film a year later.
  • Related in the Adaptation: The original screenplay had Scott and Janie as unrelated characters, only for Shane to edit the script to make Janie Scott's sister. This is mainly notable because he averts the Race Lift trope, keeping Janie played by a Latina actress and keeping jokes in the script of people making fun of her ethnicity, even though her brother and her father are both clearly white (a minor Adaptation-Induced Plot Hole).
  • Retail Riot: There's an extended sequence showing humorous mayhem and carnage at the mall on Black Friday.
  • Second-Act Breakup: Happens around the end of the movie, when Tori walks in on Heather sexually assaulting Scott, thinking that Scott was cheating on her. Scott wins her back by shaving his head and apologizing for how much he was a Jerkass to her throughout the years.
  • Shout-Out: This movie is a constant barrage of forced pop culture references.
    • The second act of the movie revolves around a series of dares Tori gives Scott, the "Fuck-It List", a reference to The Bucket List.
    • There's some pop-culture shout-outs involved in Joel trying to give Janie her "perfect date" too, like talking up her all-time favorite film What's Eating Gilbert Grape and serenading her with the theme song from her favorite show Degrassi: The Next Generation.
  • Sickeningly Sweethearts: Marissa and Gil.
  • Stalker with a Crush: Both male leads (Shane Dawson as Scott and Drew Monson as Joel) are this trope but played sympathetically — Scott gets hit by Tori's car in the first place trying to stalk Heather using his phone, and then switches to stalking Tori herself the next day. Joel's obsessive Internet research on Janie is also presented as though it's supposed to be romantic.
  • Teens Are Monsters: High school was not kind to Tori, as she was a victim of bullying and was called "Tori the Whorie", a name meant to be ironic, by her classmates.
  • Thanksgiving Episode: The whole movie takes place in the five days of Thanksgiving weekend (starting the Wednesday night before Thanksgiving and ending the Sunday afterwards).
  • That Makes Me Feel Angry: People in this movie spend a lot of time narrating their emotional state, once things start to get serious. (The Hypocritical Humor where Tori makes fun of The CW shows for doing this doesn't actually change this fact.)
  • Toilet Humor: A lot in the movie, as expected from a Shane Dawson production. Particularly there are a lot of jokes revolving around feces.
  • Token Black Friend: Tori's new best friend from college is an extremely stereotypical example of this trope — specifically a sassy black gay best friend.
  • Totally Radical: Done intentionally, with Janie coining the phrase "totes retar" in order to try to fit in with her friends, who celebrate at having finally succeeded in corrupting her when she says it.
  • Vomit Indiscretion Shot: Tori gets vomit graphically splattered all over her in the opening scene of the film.
  • What Does She See in Him?: It doesn't make any sense, including to the other characters in the movie, how hung up Scott is on Heather and how depressed he seems to be about her dumping him.
  • Wild Teen Party: A couple happen throughout the movie.
  • World of Jerkass: As is common for a raunchy teen comedy, although it's definitely played up with the opening scene of everyone tweeting and the Black Friday Retail Riot.

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