Sausage Party, the star-studded adult-oriented cartoon about sentient foods trying to escape their fate, is a welcome reminder that animation can be more than family entertainment that’s primary purpose is to distract children and sell happy meals. Animation is a medium of unprecedented artistic freedom that should attract adults as much as children, even if only for the privilege of seeing cutesy cartoons get into R-rated antics.

Though it may well prove to be the most successful film to explore the more risqué side of animation, Sausage Party is far from the first film to do so, so let’s look at the raunchy, boundary-pushing cartoons that paved the way.

Fritz the Cat

This entire list could be filled with films from Ralph Bakshi, the director who created an alternative to mainstream, family-oriented animation with a string of adult films that weren’t afraid to sexualize cartoons.

Fritz the Cat was his 1972 debut, following a rascally opportunistic cat who goes with the flow of ‘60s counter-culture for the sole purpose of hitting on female cats and, in one memorable sequence, a curvy black crow. In its time, the film offended many for mixing animation and pornography, though today it stands as a time capsule and biting satire of oft-romanticized ‘60s social movements.

South Park: Bigger, Longer & Uncut

South Park’s creators Trey Parker and Matt Stone built their show’s foundation on fearless use of free speech that pushed the boundaries of what could be put on television, and they brought the same eagerness to offend to the big screen when they released a movie based on their series in 1999.

The meta storyline follows the boys as they see a raunchy Canadian animated movie that broadens their four-letter vocabulary, shocking their mothers and sparking a war against America’s neighbors to the north. Parker and Stone find plenty of new, tasteless territory to cover in the long-form medium — including a talking clitoris and Saddam’s prosthetic penis — but the movie succeeds thanks to its clever satire of American censorship and a slew of unforgettable songs.

Heavy Metal

One of the few feature films based on a magazine, Heavy Metal contains all the science fiction and erotica that made it a cult favorite among comic fans in the mid-70s. The film, directed by Gerald Potterton and produced by Ivan Reitman, is anthology and as such doesn’t have much in the way of plot, instead using a framing story about a mysterious evil orb to launch into a series of sci-fi stories linked primarily by their excessive violence and sexual overtones.

Today Heavy Metal feels unmistakably dated, the product of the age of arena rock and hair metal, and yet oddly influential for its fearlessly distinct tech-noir style.

Anomalisa

No matter the film, screenwriter Charlie Kaufman’s downtrodden point-of-view tends to shine through his characters, even if those characters are 3-D printed puppets instead of real people.

Adapted from a similarly unconventional play, Anomalisa feels appropriately confined to one place and time, concerning the miserable depression of a traveling writer (David Thewlis playing the lonely loser that populates most Kaufman films) who perceives everyone around him to be the same, until he meets a shy woman named Lisa (Jennifer Jason Leigh) whose voice is the first unique one he’s heard in ages. Though as difficult to love as its self-centered protagonist, Anomalisa is truly a one-of-a-kind film, loaded with surreal psychological undertones that make every hilariously mundane interaction feel like a recurring nightmare.

Cool World

Who Framed Roger Rabbit? Wasn’t quite as innocent as its PG rating might suggest, but it can’t compare to its fellow animation-live action hybrid from four years later, Cool World.

This Ralph Bakshi film was heavily rewritten during production, which might explain the confused plotting of this story about an animator (Gabriel Byrne) who becomes immersed in a bizarre cartoon world he created though it can’t explain the shoddy blend of animation and reality that occasionally distracts from the story. Since this is a Bakshi joint, Kim Basinger voices an animated seductress Holli Would, a cartoon so sexualized she makes Jessica Rabbit look wholesome by comparison.

Waking Life

Though not conventionally raunchy, Richard Linklater’s rambling philosophical meditation Waking Life is certainly not meant for children. Our passive protagonist wanders through mind-opening conversations with enthused strangers in between attempts to rouse himself from the permanent dream world he’s apparently trapped inside.

The heady content of the film—touching on, among other things, the meaning of dreams, the impossibility of free will and the ability of film to capture “God”—is matched by its ever-morphing, dizzying animation style, a medium called rotoscoping in which animators trace over film footage of real actors.

Ghost in the Shell

Uninitiated viewers could be forgiven for thinking there’s little more to the Ghost in the Shell movies than the hand-drawn cleavage of Motoko, the curvy female cyborg at the film’s center.

The violence and sexuality of Japanese animation heavily informs the style of Ghost in the Shell, but the uneasy tech dystopia world of the film franchise that began with the 1995 original owes just as much to Blade Runner. Motoko’s role in the hunt for a hacker known only as the Puppet Master offers plenty in thrills, while the character slowly turns from an animator’s wet dream into a fully realized character who, despite being mechanical, gives us valuable insight into what it means to be human.

The King of Pigs

The violence in The King of Pigs — a South Korean animated feature from 2011 — isn’t stylized like the sci-fi world of Japanese anime, but grounded in a recognizable world of social injustice that makes every drop of blood sting the audience as much as the characters.

There’s plenty of violence and anger to go around in the film from director Yeon Sang-ho, which follows a pair of old middle school friends who reunite and reminisce after one of them impulsively murders his wife. The evils of both friends’ current lives are traced back to the all-important class conflicts that labelled them as “pigs” for their lack of wealth as children, making The King of Pigs a powerful, fearless look at the prejudices that still plague South Korean society.