As movie-goers, we are all familiar with that excruciating moment when you are watching a movie and the action is so horribly uncomfortable that you actually feel the need to cover your own face. It’s this nonsensically powerful moment when you actually feel embarrassed for a fictional character because of some terribly awkward scenario that you’d rather watch a murder than bare witness to. It’s like a horror movie almost – it’s that same turtle reaction where you just want to shrink away. And like horror, it’s either done really well or it’s abused, which is why I want to share with you the films I think did it the very best. Oh, and if you are wondering why I only picked 9 – it’s the most awkward number I could think of.

If it were up to me, every movie would be required at least one musical number. Seriously, every movie. Children Of Men would have a song in it, Sophie’s Choice as well. Why? I don’t know – it would be funny I guess. Fine, so it’s probably not a great idea. I take it back. I just get excited when a song becomes the center of a scene – especially in comedies. People rarely have the nibs to stick a good musical sequence or two in their non-musical genre films, so let’s take a moment to pay our respects to those who did it so well by arbitrarily judging them in list form.

The other day, while I was supposed to be in the middle of working on a major project, I found myself eyeball-deep in a friendly conversation covering many years of terrible sex decisions. My buddy and I went back and forth sharing stories that spanned from high school to last Tuesday, each adventure something we were both proud and ashamed of. Just like sticking your hand on a hot stove will teach you to never do that again, these individual moments in our collective history were lessons we learned from—even if they were decisions we’d make more than once. The whole sordid affair got me thinking the next day: “wouldn’t it have been easier to learn from a movie that sleeping with a man on his friend’s makeshift innertube air mattress was probably not the best choice?” I mean, isn’t that what films are supposed to do? Provide audiences with entertaining life experiences that seem too exaggerated to be real? I’ve always appreciated films that present sex as both art and entertainment, but what sometimes makes an onscreen sexual moment memorable is when both the characters and the audience can learn from it. Thankfully for us (well, me), there have been a few films in recent memory that offer pertinent life lessons when it comes to bedroom activities.

Although certain politicians and even scientists will suggest otherwise, most agree our basic human desire for sex remains pretty unchanged. Over the centuries we’ve acknowledged that ladies like it just as much as the men folk, both sexes can be completely uninterested, and there’s also the possibility that same sex lovers getting down and dirty isn’t, in fact, dirty. Every new generation accepts something as tame that the previous generation thinks taboo. My mother finds the practice of bondage troubling, but the idea is ordinary to me. Whereas I don’t quite understand her fascination with the word “slutpuppy” because that’s just ooky. I’m not saying one generation is better than the other, I’m more curious about how we got to the place we are. I am pretty in tune with the going-ons of Gwen, so I have no problem pinpointing a lot of my sexual identity development happening simultaneously with the films and TV that I watched in the 90s. Thinking back, the 90s stand out to me as a hodgepodge decade when it came to sex in film. We had the renewal of romantic melodramas as a reaction to the social commentary-filled erotic thrillers of the 80s, the depiction of realistic sex in comedies, and the rise in popularity of rape culture. Of course all these themes wouldn’t have been possible without the decades before them, but something happened in the 90s that made sex seem pleasurable through love, humor, and invasion.