In Three Easy Pieces, I deconstruct one specific genre of pop culture, from its birth through how it exists today. This month, I'm looking at cartoons for adults. When did animation shift from a medium cultivating imagination in kids to something to expand the minds of grown-ups?

BIRTH: Fritz the Cat

Honorable mention: Fantastic Planet, The Plague Dogs, Heavy Metal

Is Fritz the Cat (1972) a good movie? Well, no. But did it ever set out to be something people might consider a "good" movie? I doubt that word ever passed director Ralph Bakshi's lips during this cartoon's creation. Still, it wouldn't make sense to start with anything other than this, the first ever X-rated American cartoon -- a hugely successful movie that pulled in more money than the majority of Disney pics at the time, and helped usher in not only a new era of freewheeling sleaze in animation, but helped break down barriers for themes available for exploring in the medium.

Fritz the Cat is a grimy slimeball of a movie, taking inspiration from Robert Crumb's art, but using that as a springboard to explore puerility, offensive caricatures, and muddled political observations. Crumb famously denounced the film, particularly in how it depicted Fritz, even going so far as to publish a comic killing off the character. Bakshi's grotesque, violent, hyper-sexual and hyperactive style would also prove influential, inspiring further generations of animators to spend a little more time in the gutter.

DEVELOPMENT: Waking Life

Honorable mention: Grave of the Fireflies, Ghost in the Shell, Little Otik

The years since the ‘70s boom of adult cartoons would prove to be ecstatically fruitful ones, especially when it came to developing a better sense for mature themes and more dimensionalized characters. Any number of Studio Ghibli films, for instance, would be ripe for exploring in this category, but I'm partial to Richard Linklater's Waking Life (2001), a dizzying dive into the deep end of philosophy, metaphysics, and the inscrutable power of dreams.

Some may criticize Waking Life as another exercise in intellectual self-gratification from the director of Slacker, the Before... trilogy, and A Scanner Darkly, but it feels alive and unpredictable in a way that so many animated films simply don't. Shot on digital video and then rotoscoped by a team of artists who were all essentially given free reign, stylistically, the film drifts from talking head to talking head, our dreamer (Wiley Wiggins) forced to be an audience to one insane scene after another. Philosophizing actors, teachers, comedians, performance artists -- a young Alex Jones even shows up, unfortunately enough -- draw you and our hero further into an overload of ideas that's as unnerving as it is invigorating.

See it with other people, and you'll want to talk for hours after.

TODAY: Anomalisa

Honorable mention: It's Such a Beautiful Day, Persepolis, Tower

We've talked about rotoscoping and traditional animation, but we haven't touched on stop-motion animation. Anomalisa (2015), the first R-rated animated film to be nominated for an Academy Award, at first seems like there's no real reason for it not to be a live action film. Centering around a fairly mundane story of a customer service expert (David Thewlis) giving a talk at a boring convention in Ohio, there quickly rises some surreal experiences. With the whole thing stop-animated with puppets, the only voices are Thewlis, his love interest Jennifer Jason Leigh, and every other part voiced by Tom Noonan.

This oddity of a film was co-directed by Charlie Kaufman and Duke Johnson, based on a play by Kaufman. What starts as a quirky choice to have every non-essential character voiced by the same person turns into the crux of the film, without giving too much away. Shying just a little bit away from the mind-melting movies that Kaufman is known for, the majority of Anomalisa is played completely straight; in addition to most of the film being one realistic scene after another, the film also features one of the most true-to-life sex scenes ever put to film, animated or not.

In making a film that might otherwise be just fine as a live action film, save for a fundamental restructuring of reality that couldn't happen otherwise, Anomalisa utilizes animation in a way otherwise unforeseen in the genre.

Three Easy Pieces will return, next month, with: Wrestlers in Movies