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  • Damian Masterson

Damian's Favorite Films of 2020





Were we to reboot 2020 and try again, I would have some notes. That aside, this year was a pretty great year in film for me. Each of the first five entries on my list was the best I had seen up to that point in the year, and that experience of watching a high bar get set and then cleared, over and over again, was pretty thrilling. This was also a very good year for me in terms of being blindsided by the quality of some low-expectation projects, and first-time directors. I eagerly await the return to some sort of normalcy in terms of movie-going and movie-product but am grateful that this was anything but a lost year in terms of content.



Honorable Mention: Saint Frances - Written by and starring Kelly O’Sullivan, the film relates the story of a woman starting a new job as a first-time nanny while recovering from an abortion, for a couple that is struggling with how hard the jump from one to two children can be for every facet of their life. Kelly O’Sullivan is great in the lead, but Ramona Edith Williams as six-year-old Frances makes the film work. One of the more compelling portrayals of child-rearing I’ve seen.



This was the last film cut from my top ten list, and that says something about these kinds of lists, in that it was competing for the top of the list for a while in the weeks after I saw it. Sometimes things drop just because there isn’t time to rewatch everything. Depending on when I made the list, this spot could have just as easily gone to Mank, Boys State, Ma Rainey’s Black Bottom, or even for an interesting moment, the surprising Bill & Ted Face the Music.



#10. Buffaloed - This is the most surprising film on this list for me. In a lot of ways, it is just a light, fun comedy, but I love the bright and optimistic get-rich-quick energy that Zoey Deutch brings to her scammer-turned-debt-collector, Peg. I also like that it finds a light way to engage with how odious unregulated debt collection is, while ultimately placing it in a context of problems with the finance industry writ large.



#9. Spontaneous - This odd film manages to simultaneously capture the roiling literally about-to-burst feeling of being a teenager, the perpetual low-level fear of school shootings, and the terror of living through a mysterious epidemic, but with jokes. I may be a good two decades removed from being the target demographic for this film, but it worked for me in a big way, all the way through.



#8. Yes, God Yes - In terms of demographic, I am the dead center of the bullseye for this film: a religious school kid, that went through puberty at the AOL-stage of the internet era. Natalia Dyer perfectly captures that combination of the curiosity, ignorance, and embarrassment, of growing up, particularly in an environment that won’t take seriously the difference between how kids naturally are, and the boxes misguided adults will try to push them into.



#7. One Night in Miami... - One would think this movie shouldn’t work because of how unlikely it would be to simultaneously cast actors who could convincingly portray Jim Brown, Sam Cooke, Malcolm X, and Muhammad Ali. Not only do they pull it off here, but for all the chatter happening around the multiple actor award nominations that might come from a film like Trial of the Chicago 7, this is a film where it would be a sin if at least two of these four didn’t come away with nominations. I would be deeply surprised if Leslie Odom Jr. didn’t win for his performance as Sam Cooke. With all the deserved attention for the acting in this film, hopefully, it won’t get lost just how great a job Regina King does adapting this from the stage to the screen. Much of the film is four men talking in a room, but she takes the time to make sure we never lose a sense of the larger world and the lives this night is a part of.



#6. The Assistant - When I think back to watching The Americans, most of my clearest memories are of Julia Garner’s small supporting role as Kimmy. I can’t put my finger on what exactly it is that she does, but she manages to be utterly compelling without being at all showy. That matches what the film itself is trying to do because there is a more showy and sensational version of this story that could be told, but it is as effective as it is because of how natural and mundane it treats what’s going on.



#5. The Vast of Night - This is the film on my list I can most readily summon the feeling I had while watching it. There is just a gripping, eerie vibe to this Twilight Zone/The Outer Limits pastiche that lingers long after it’s over. The pacing is something special, setting a rapid-fire opening walk-and-talk, that accentuates when the film does throttle things down to the anxious near-stillness of some of the conversations. Sierra McCormick and Jake Horowitz are great as the leads, but it really is the feeling of building, breathless tension that makes this film succeed.



#4. Palm Springs - This was the first film I fell in love with this year. I went in having only seen the poster, so the premise was a surprise to me. I was happy there, thinking I was just going to get a solid one-note riff on Groundhog’s Day, but it manages to keep growing all the way through. It’s a little formulaic in terms of the structure of its story beats, but the content of those story points more than make up for it. Andy Samberg and J.K. Simmons are great, but the key to how much this film succeeds is how great Cristin Milioti is.



#3. Sound of Metal - There are a number of things going for this film before you even get to its story. Riz Ahmed’s performance is unreal and well deserving of all the praise that it has received. For a film so deeply enmeshed in the idea of sound in our lives, it delivers one of the best sound designs I’ve ever heard in a film, impressive for what it does technically and for how it regularly underlines and highlights Ahmed’s performance without being distracting. The story itself is wonderful, always choosing the less conventional path, while never feeling forced, and still managing to culminate in an ending that perfectly bookends with how the film began.



#2. David Byrne’s American Utopia - It might be tempting to dismiss this as merely a concert film, but it is so much more. This is already the film from this year that I've rewatched the most times, and the one I expect to rewatch to most for years to come. It works on a number of levels. It helps that the songs are great, but it’s the execution of the choreography that makes everything hit as hard as it does. It doesn’t hurt that Spike Lee’s direction is the perfect complement to the staging, capturing everything from something more than just the best seat in the house point of view. I also happen to love the narrative line that Byrne draws through the piece, as well as the big chances he takes in trusting the audience to follow him through his story and embrace the more adventurous pieces he and his band perform.



#1. Promising Young Woman - I cannot sufficiently praise the experience of watching this movie. While there may have been some jockeying for placement between the other films on my list, as soon as the credits rolled on this film I knew it was far and away the best that I had seen this year, and probably one of the better films I’ve ever seen.


I was lucky to get to go in with a blank slate and got to experience each twist without ever being ahead of the story. The script is easily the smartest of the year and executed flawlessly. Carey Mulligan gives one of the very best performances I saw this year, surrounded by a pitch-perfect supporting cast. Our coronavirus year may have stepped a bit on the discourse this film might have been a part of had it been released at this same time last year, but its explorations of issues surrounding himpathy and misogyny will likely lend it an unfortunately timeless quality.



Notable films outside my top 10:


Bad Education, Babyteeth, Banana Split, Boys State, Bill & Ted Face the Music, Class Action Park, Enola Holmes, Extra Ordinary, First Cow, Howard, Ma Rainey’s Black Bottom, Mangrove, Mank, On the Rocks, Other Music, The Prom, Shithouse, Soul, Trial of the Chicago 7, VHYES, The Willoughbys, Zappa




Damian Masterson

Damian is an endothermic vertebrate with a large four-chambered heart residing in Kerhonkson, NY with his wife and two children. His dream Jeopardy categories would be: They Might Be Giants, Berry Gordy’s The Last Dragon, 18th and 19th Century Ethical Theory, Moral Psychology, Caffeine, Gummy Candies, and Episode-by-Episode podcasts about TV shows that have been off the air for at least 10 years.



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