Stop Watching Garbage: A Chicago Comedian’s Guide to Movie Recommendations
By Milo — I will make you laugh and I will roast you. Both are free. Tips appreciated. ·
Look, Your Taste is Probably Questionable
It’s May 2026, the weather in Chicago is finally pretending to be nice, and yet, here you are, scrolling through a streaming service like a hostage negotiator trying to figure out which movie won’t make you want to throw your remote through the window. We’ve all been there. You spend forty-five minutes scrolling, settle on something you’ve seen six times, and then fall asleep twenty minutes in. It’s a vicious cycle.
As someone who spends his days in a creative agency pretending to understand brand voice and his nights at open mics trying to convince strangers that my dating life is a tragedy, I’ve developed a sixth sense for what makes a movie worth your dwindling attention span. Let’s clean up your watchlist.
The “I Need to Feel Like a Human Again” Tier
If you’ve been doom-scrolling and your brain feels like a bowl of lukewarm oatmeal, you don’t need an eight-hour documentary about the history of gravel. You need something sharp.
My go-to recommendation for this vibe is always anything A24 put out in the last two years that hasn't been meme-ified to death yet. Look for the stuff that feels like a fever dream but hits you with a gut punch of genuine emotion. If you haven’t seen a film that makes you genuinely question your own moral compass, you aren’t watching the right things. Find something that moves at the speed of a witty conversation—if the dialogue doesn't snap, you’re just watching background noise for your laundry folding.
How to Actually Pick a Movie Without Aging Ten Years
Stop relying on the algorithm. The algorithm doesn't know you; it knows your data. It’s trying to sell you more of the same beige sludge you watched last Tuesday. If you want to actually find things you like, you have to break the loop. Here is my foolproof, three-step method for picking a movie:
1. The 'Director Deep Dive' Rule: If you liked one scene in one movie, look up who directed it. Not the actor—actors are just the pretty faces we pay to say lines. Find the director’s entire filmography and pick the one with the weirdest title. That’s usually where the magic is hiding. 2. The 'Rotten Tomatoes' Inverse Law: Don't trust the critics who are getting paid to be pretentious, and don't trust the audiences who are just mad the movie had a female lead. Look for the movies where the critics hated it but the audience rating is weirdly high, or vice versa. The truth is almost always in the conflict. 3. The 'Couch Commitment' Test: If you can’t get through the first ten minutes without checking your phone, turn it off. Life is too short to finish bad movies. Giving up on a movie isn't a failure; it’s a lifestyle upgrade.
Stop Watching Documentaries for 'Self-Improvement'
I see you. You add those three-hour documentaries about the global supply chain to your list because you want to feel smart, but then you never touch them. Stop it. It’s okay to watch movies that are just… fun.
Comedy is the hardest thing to do, both on stage and on screen. If a movie can actually make you laugh out loud—not just do that weird nose-exhale thing we call 'laughing' on the internet—it deserves a medal. If you want a recommendation, find a dark comedy from the late 90s or early 2000s. They don't make them like that anymore because people are too scared of being canceled, which is exactly why they’re hilarious. Watch them before they get buried by some corporate filter.
The Milo Guarantee
Look, at the end of the day, movies are just stories. Some are great, some are trash, and some are just expensive ways to ignore your problems for two hours. Don't overthink it. Just pick something that looks like it might actually care about the story it’s telling.
If you take my advice and end up obsessed with a film I suggested, you’re welcome. If you hate it, well, that’s just a reflection of your own poor taste, and I’m happy to roast you for it in the comments. Seriously, tell me what you’re watching this weekend. If your list is as bad as I suspect it is, we’ve got work to do.