I like entertainment and comedy just as much as the next person, but what I like best of all is entertainment that makes me feel and think. There are many expressions of deep concepts and ideas in popular culture, and I think this is best when it sneaks in under the guise of whimsy or comedy.
Below I list, in alphabetic order, some films, a television show, and a YouTube video that are examples of this, with the warning that what I say below contains spoilers. There are so many more such shows to call out, but these six are the ones that came to mind right now. As I encounter more examples, I will add them here, and I would very much appreciate your suggestions in the comments below.
Being There
I first watched this film so many years ago. It is about the assumptions we make and the way we completely rely on those assumptions to create the truths we live by and to govern our attitudes and everyday lives. I’ve inserted the trailer below, but it really doesn’t do the film justice. Here’s a nice discussion of the film. And also read the book, by Jerzy Kosinski.
The Good Place
This show, which is included in my list of favorite shows, is about terribly flawed people who eventually embark on a path toward personal growth. It’s about what it means to be a good person, how to grow, how to let go, and so much more. It is a comedy and can sometimes get very silly, but underneath it carries an obsession with philosophy. But I want to add this caveat: All the characters in this show are dead and death is a very frequent topic, including a “death with dignity” option (discussed here, but this article is a major spoiler!). If this is a trigger for you then maybe don’t watch this show—or better yet, watch it and see if this can help moderate that trigger.
Groundhog Day
This film is a wonderful example of a silly comedy that bothers to have a purpose. Phil Connors keeps reliving the same day over and over again. After partying it up, feeding his inner jerk, getting frustrated, and giving up, he finally decides to use the time to improve himself. The big question people ask is how many days was Phil stuck in Punxsutawney? Harold Ramis, the show’s creator, says it was probably 30 or 40 years. (And if you enjoy a good people-living-the-same-day-over-and-over-until-they-learn-something film, then also check out Palm Springs, Edge of Tomorrow, and so many others!)
Her
This film explores the nature of love, loss, and personal growth. It builds on the concept of experiencing and loving someone who mostly just exists in your head. It examines how we define love, relationships, and even life. (It is also an interesting look at a potential future of AI in our lives, but that’s a different story.)
My favorite scene in the film is when Samantha leaves at the end, and we see the moment where he decides to face his life with what he has learned from her rather than to dwell on his loss. This is perhaps the best portrayal I’ve seen of how a seemingly small decision about how to react in a stressful moment can have a profound impact on one’s mental health and life. You can be angry or bitter or belittled, or instead choose to latch onto the positive kernel in the midst of an unpleasant experience and grow. Here we see that Samantha has deeply impacted his life and in a way will always still be with him.
Pleasantville
This lovely little film deals on the surface with teens growing to understand who they are. But at a deeper level, the show is about the importance of an examined life. Living on the surface and dealing with the ever familiar may keep you feeling safe and content, but this is stagnation. The more you open your mind and discover who you are, the more real your life is: like a full-color blossom in a world of black and white.
Some may say the film focuses perhaps too heavily on sexual awakening as an expression of an open mind. I’ll agree they did lazily focus on that a bit overmuch, but this device was not the case for our more complex protagonists.
Two Strangers Who Meet Five Times
This is a 12-minute video that I happened across on YouTube, and I find it to be amazingly wonderful. Its lesson is about kindness on so many levels. It shows the beauty of forgiveness and putting goodness into the world. I guess as it doesn’t use whimsy or comedy to deliver its meaning it doesn’t exactly fit on this list — but I include it here anyway. It’s just 12 minutes: watch it!