The Naked Gun: From the Files of Police Squad! (1988) by Shawn Bourdo
Is anyone going to pick anything other than a comedy? Do you watch Kramer Vs. Kramer to feel good? But the term "to feel good" all by itself suggests that you are feeling bad to start. Well, The Naked Gun is a perfect tonic to that for me. It's even crazier and more simple than Airplane. I can drop in on this film at any point and start to instantly feel better. The combination of non-stop gags, not worrying about a plot and the fun of guessing all the guest stars makes this perfect popcorn fare. I will watch this through the darkest of days.
Labyrinth (1986) by Amanda Salazar
Even when I just think about this film, I feel good. A big smile comes across my face and I start quoting it, or worse singing some of the original tunes from it. My go-to film that always puts me in a great mood, is Jim Henson's Labyrinth. I have always been a fan of fantasy and puppetry, and well, this film obviously combines the two perfectly. A young Jennifer Connolly plays Sarah, who wishes that her younger brother Toby be taken away by the Goblin King, Jareth (played by David Bowie). When he does she has to complete the Labyrinth in less than 13 hours and get to the castle to save him before Toby is turned into a Goblin. Along the way she meets the most interesting characters and comes away with an eclectic group of friends, including a dwarf, a talking dog, and a huge beast. In true Henson fashion the film is mysterious, even scary at times but always playful. Bowie is such a treat in this film that he is what is remembered most. Not only did he compose the original songs in the film but even the costumes that he is in are worth a viewing. Labyrinth is a timeless film that taps into the child in all of us and every time that I watch this film, I feel good.
Top Hat (1935) by Dusty Somers
Really, any Astaire-Rogers collaboration would fit the bill here, but I'll go with Top Hat, which features a typically romantic Irving Berlin score, a ridiculous mistaken-identity plot, and some of the most sublime dance numbers ever put on celluloid. No matter how risible the plot can get in the Astaire-Rogers films -- and it's a serious offender here -- it's nothing the soft shoe of "No Strings," the comic imitation of "Isn't this a Lovely Day" or the romantic strains of "Cheek to Cheek" can't easily overcome. This one will put a silly grin on my face from credits to close.
The Music Box (1932) by El Bicho
This one is a bit of a struggle as so many films come flooding to mind that it almost feels unfair to highlight one, but I am going with "The Music Box" starring Laurel and Hardy. This Academy Award-winning short is a classic with a simple premise: Stan and Ollie need to deliver a piano up a flight of stairs. However, nothing is ever easy as it should be when these two are involved and hysterical chaos ensues. Doesn't matter how many times I watch it I laugh throughout, no matter if I remember what's coming or not. Kudos go to the production crew who help realize gags that seem like they should be in a cartoon.