The Challenge: The Top 5 Most Depressing But Entertaining Movies
Ken Jones, OnScreen Blog Chief Film Critic
‘The Challenge’ is a new series where Greg Ehrhardt, editor, and columnist for the blog, challenges Ken Jones on his cinematic knowledge to better inform readers about the deep catalog of movies we can enjoy today.
With Oppenheimer coming out this week, Ken’s challenge was coming up with his five most entertaining movies based on super depressing premises.
The movie itself has to be depressing but still entertaining and fairly rewatchable.
We decided to rule out almost all war movies because whether the movie is depressing could come down to a point of view. Ken’s mission is to come up with five movies that are objectively depressing but still entertaining, much like we suspect Oppenheimer will be based on early reactions.
Read Ken’s answer below and tell us on Twitter (@onscreenblog) how well you think he did.
Ok, I have to say this is not an easy list. I initially compiled a list of about 35 and whittled it down. Some of the hardest omissions were some of the most obvious ones, like Schindler’s List, which is a great film, and there are a ton of great descriptors for it, but I wouldn’t apply “entertaining” to it.
5. Tower (2016)
Part of the reason for these lists is to promote and elevate more movies for people to check out, so this is a hidden gem. The documentary employs rotoscoping (animation layered over live-action) to bring to life first-hand accounts of the first mass school shooting in US history at the University of Texas in 1966.
The events of the day are reenacted while the victims and witnesses recount their personal stories from that day and the horror on the ground. It is an inventive way of recreating the past and giving the story life. Also, it consistently foregrounds the people on the ground over the man in the tower with the rifle.
4. Everest (2015)
Director Baltasar Koramkur’s film depicts the 1996 Mount Everest disaster, where several groups of climbers got caught on the mountain in a blizzard. At the time, it was the deadliest event on the highest mountain in the world. Despite the unfortunate fates of most people on these expeditions, this is a genuinely thrilling movie.
Jake Gyllenhaal, Josh Brolin, Jason Clarke, and John Hawkes top a deep cast, but what impresses me about this movie is the cinematography which will make you feel like you are on the mountain. Seeing this on the IMAX when it was released was a dizzying treat.
3. Memories of Murder (2002)
Bong Joon-ho won over audiences with 2019’s Parasite, but in 2003 he made a detective thriller that is based on a string of serial murders from 1986 to 1994 that shook a rural South Korean community; it’s also believed to be the first case of a serial killer in South Korea. This police procedural is gripping and unconventional, and utterly captivating.
It’s also ambiguous as it was an unsolved case when it was made. However, there was a DNA breakthrough in 2019, and the murderer was found. For years, this film was hard to find in North America, but in recent years it has gotten a Criterion Collection Blu-ray release, and for a time, it was streaming on Hulu (where I first watched it).
2. Margin Call (2011)
Margin Call is one hell of a debut film from J.C. Chandor, using a fictional investment bank to depict the early stages of the 2007 financial crisis that led to the Great Recession. Margin Call has a loaded ensemble cast (unfortunately, a problematic Kevin Spacey is prominently involved) and a script heavy on financial dialogue. Don’t let the jargon-laden dialogue deter you, though, because it is a surprisingly easy film to follow as the discovery of disaster on the horizon breaks and everyone goes into crisis management mode. This movie is smart, taut, and Sorkin-esque in how talkative it is.
For years, films have been judged by their rewatchability if you stumbled across them on cable TV. Margin Call is for the YouTube generation, though, with several scenes that you will just want to pop on from time to time to watch a great actor have a great moment, like Jeremy Irons's board room scene.
1. Zodiac (2007)
David Fincher’s telling of the story of the Zodiac Killer, Zodiac, was a film that earned high praise in 2007 when it was released, but it got lost in the shuffle of one of the greatest years of movies ever. However, since then, it has only grown in esteem and is considered a masterpiece near the top of Fincher’s impressive filmography.
The Zodiac Killer gripped the Bay Area and the nation in fear, and Fincher captures that as few directors could, burrowing into the obsession over the case for the men at the heart of the investigation, portrayed by Jake Gyllenhaal and Mark Ruffalo, working the journalism and police angles respectively. The tension in the scene where Gyllenhaal’s Robert Graysmith goes down into a basement on a dark, stormy night is palpable.