One of the most underrated and enjoyable films of the late 1980s, Adventures in Babysitting starred an incredible cast including Elisabeth Shue, Vincent D'Onofrio, Keith Coogan, and Anthony Rapp. The ultimate babysitter adventure, it dealt with a teen who felt "too old to babysit" stuck watching a child, her older teen brother and his best friend for a few hours.

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While we loved the dangerous and hilarious adventures that the group found themselves on that night, looking back, we have to admit that plenty of the content, particularly lines and scenes meant to be humorous, really didn't age all that well.

Insulting Thor

Not only is it not okay to call anyone a "homo," as Brad Anderson routinely did in Adventures in Babysitting, but it's also not okay to consider being dubbed a member of the LGBTQ community an insult, either. While there are unfortunately plenty of people who still think that way, it's thankfully being phased out as youth with open minds grow up and accept people as they are.

Brad could have easily thrown any other insult at Thor, played by the fantastic Vincent D'Onofrio, rather than the one he used in the original movie, and given it more evergreen content. Even the trite insult of "loser" would have worked better in this case.

The Playboy

While the 1987 film is considered a crime/thriller, it's also a comedy and a film watched by many families, especially since it featured a cast of mostly children and teenagers. That's why featuring a Playboy magazine as not only a running gag but a plot point was rather inappropriate for the movie.

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Comparing Chris Parker, portrayed by the lovely Elisabeth Shue, to the model in the magazine became tired, with the joke being used over and over again. The Playboy content certainly hasn't aged well since, especially with regards to how often kids in the film, including young Sara Anderson, ogle it.

Daryl's Jokes

Daryl Coopersmith seemed like a riot to the kids and teens who watched the move back in the '80s and '90s, but today it's almost uncomfortable to listen to some of his jabs throughout the film, particularly when he jokes about being assaulted in the city.

This is one of the most common parts of an older movie that doesn't age well. As humans evolve, so does our sense of humor and understanding of right and wrong, and while some may accuse the current culture of being full of "snowflakes" or "too PC," in reality, marginalized people are finally getting a voice and viewers demand more intelligent humor that doesn't hurt people in the process.

Daryl Taking Advantage Of Brenda

When the gang finally meets up with poor Brenda, who's had a night of her own between guns, rats and more, she's exhausted and falls asleep in the car. One would think that the rest of the kids would also fall asleep while Chris is trying to out-drive the Andersons home, but Daryl is not only wide awake but very interested in the sleeping Brenda's anatomy.

While Brad admonishes him, we're still meant to laugh at this as if it's a harmless little prank, looking down someone's shirt while they are sleeping. It's even worse than Troy doing it in The Goonies because  he's meant to be a villain, and the awake Andy tells him off.

The Glamorous Prostitute

On Daryl's many adventures, he runs into a 17-year-old prostitute (played by Chris Columbus' wife, no less) because of course he does. She says she really wants to get to know him, and she looks beautiful and glamorous. A scene where a 15-year-old and a 17-year-old discuss the oldest profession aside, today's movies are not likely to glorify prostitution like this.

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Viewers know that many prostitutes like this one are teens who ran away from abusive situations and often face just as much, if not more, abuse on the street. Not exactly something that should be played for laughs.

It Drops The F-Bomb Multiple Times

Adventures in Babysitting is a PG-13 film, but between gang violence, lots of sexual references and adult situations, it seems to push the rating a bit, especially when up against today's films with similar ratings. While we're more likely to see more violence today in, say, a PG-13 comic book adaptation, we're less likely to hear the F-bomb dropped, let alone by both a gang leader and the babysitter herself.

It's one of the most hilarious scenes in the film, but it likely wouldn't make it to a modern PG-13 movie, and if it did, it would be limited to one time.

Daryl Makes Out With A College Woman

Many of the jokes in Adventures in Babysitting that failed to age well seem to center around Daryl Coopersmith, one of which involves him stealing a college student's girlfriend during a party. She does seem to be inebriated, especially when she makes an offer to Daryl that he thinks he can't refuse and he gets in trouble with the boyfriend to boot.

The age of consent in Illinois is 17, and there's no exception for being "close in age," even if it applied. A 15-year-old isn't "close" to a college student and this was completely inappropriate at best.

Mike Todwell Is 28

While the "so cool" Todwell is supposed to be a high school senior, he's played by Bradley Whitford, who was 28 at the time — an obvious 10 years too old for the role and looking it. Granted, Shue was 24 and much older than the 17 she was supposed to be, but today's efforts would likely be made to get younger actors for both roles. The current model is to cast younger, even for older roles, rather than the opposite, even if that's probably healthier for the actors involved.

Looking back, Todwell looks so much older that he comes off as even more of a creep by cheating on his girlfriend with a girl he openly refers to as "easy."

The Ending Doesn't Make Sense

Adventures in Babysitting

We're a lot harder on movies today, and leaving a crime leader on the side of a building to "sweat it out," while knocking out another crime boss isn't going to end the drama of the movie. After all that running, it's too quick and clean of a climax, and poor Joe Gipp would likely be offed over these actions against his bosses.

Having both men arrested would be a much better end to the story, even though Gipp would probably still face retaliation for his kindness. He'd have to have a different angle other than having an obvious role in the capture.

"Black People Are Scary"

Unfortunately, this trope is often still used in many a film, but our culture is slowly moving away from using Black people as villains all of the time. From the car-jacking to the Blues performance to the gang scene, every Black person on camera is supposed to look "scary," at least at first. This just isn't okay and would not work well in a modern film, nor should it.

We could argue that all of these situations are scary anyway, and that the kids aren't reacting to color, but there aren't any "good" Black characters, save for the anti-hero Joe Gipp, for perspective or balance.

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