1. Clue. This is one of my all-time favorite movies. So many great bits, tons of slapstick and wittily delivered lines. In our house it gets watched every single Halloween season.
2. Forgetting Sarah Marshall. One of Apatow’s best. Wish Russell Brand and Jason Segel were acting more often.
3. Knives Out. I thought the trailer made it look not-so-serious and kind of over the top goofy in a lot of ways. I was pleasantly surprised really to find it more serious, but in a Wes Anderson kind of way, without all the pastels.
4. The House Bunny. One of Emma Stone’s more underrated performances, IMO. SUCH a cute and silly movie!
5. 50 First Dates is probably my all time favorite movie. I can watch it anytime, any day, and repeatedly. Don’t care, it’s a silly romcom but I just love it.
6. Pitch Perfect is literally my favorite set of movies, mostly because they are dumb funny, and I love music.
7. Thor: Ragnarok. I think it’s enjoyable even if you don’t watch any other Marvel movies, or don’t like Marvel movies.
8. What About Bob? “Why are you all in black?” “I’m mourning the death of my childhood.”
9. The Princess Bride is a perfect movie – true love, high adventure, pirates, princesses, giants, miracles, sword fighting … it has it all.
10. Wayne’s World is always good! This is quite possibly my favorite movie, and the sequel is fucking hilarious too. My sister even bought me the Wayne’s World cap for my birthday last month!
11. Planes, Trains and Automobiles. That movie has me crying in laughter until the end. Then I’m just crying.
12. Blast From The Past. So underrated. Probably Alicia Silverstone’s best movie after Clueless and peak Brendan Frasier.
13. Paddington. He is a wise bear. Because of him I always carry an emergency marmalade sandwich in my hat in case I need it.
14. Legally Blonde is my go to feel good movie (and that’s coming from a guy in his 20’s).
15. Singin’ in the Rain (just watched it again last night). Love the old movies that are just silly fun.
16. We’re the Millers. Very very good comedy.
17. Oceans Eleven my friend. If you have extra time do the whole oceans series, even 12 has its moments.
18. Wreck it Ralph. One of the best Disney movies for sure.
19. Not quite a movie but my go-to is the John Mulaney specials on Netflix.
20. Death Becomes Her. Highly underrated film but I try to only watch it around Halloween time.
21. What We Do in the Shadows. Absolutely wonderful! There’s lots of blood though (vampires), so it’s not really kid friendly, maybe.
22. Back to the Future. I was 9 when it was released in cinemas so for me it was always an utter classic because everything – Marty’s clothes, his references, everything about his ‘realistic’ normal life was what I knew. That made the 1950s stuff more entertaining – because it was so far away from the reality of 1985.
Now people watch it and all of it his historical! 2020 is 35 years from 1985. That’s longer ago than Marty travels back to in the film – 1985 to 1955!
23. School of Rock. “I have been touched by your kids. And I’m pretty sure I’ve touched them.”
24. Game Night. Yeah, I really didn’t expect to enjoy that movie near as much as I did. Girlfriend and I laughed out asses off the whole time.
25. Rat Race. It’s so silly and ends on a silly singalong high.
26. An oldie but My Cousin Vinny. My favorite comedy of all time. And, from what I’m told, one of the most accurate portrayals of the legal system in entertainment.
27. Uncle Buck. Or any movie starring John Candy. He always delivered!
28. The Emperor’s New Groove. I love the fact that they literally fell into a plot hole. “How DID you make it here before us?” “I don’t know, by all rights it doesn’t make sense” Look at the picture. Their route falls into a hole and pops up in the palace.
29. Hot Fuzz. It’s an actual triumph. Really clever whilst remaining totally accessible. Many people love Shaun of the Dead, but I think I like Hot Fuzz more. Either way they’re both fantastic films that sustain multiple viewings.
30. Tremors. A little bit scary, a lot funny. Always a crowd pleaser. 
Source: https://thoughtcatalog.com/january-nelson/2020/07/30-perfect-movies-to-watch-with-friends-over-pizza-and-beer/