A Serious Man (2009)
Directors: Joel and Ethan Coen
Cast: Michael Stuhlbarg, Richard Kind, Sari Lennick
Always dogged by the criticism of excessive caricaturing, the Coens took a leap into the unknown with this Book of Job–like reminiscence, inspired, in part, by their own ’60s Jewish boyhoods. It vibrates with humour, sadness and a scary mystique (“Accept the mystery” is a key line of dialogue).
As Good As It Gets
Director: James L Brooks
Cast: Jack Nicholson, Helen Hunt
Grumpy older man meets lonely younger woman while befriending/insulting his gay neighbour. Both edgy and heartwarming, ‘As Good As It Gets’ is a relationship comedy about unlikely friendships and even less likely romance. When Jack Nicholson’s cantankerous OCD sufferer meets Helen Hunt’s kindly waitress Carol, it’s hate at first sight, but his grudging assistance to an injured neighbour (Greg Kinnear) brings the pair closer. Nicholson’s jaw-dropping insults make this worth the watch alone.
Monty Python and the Holy Grail (1975)
Directors: Terry Jones and Terry Gilliam
Cast: Graham Chapman, John Cleese, Eric Idle
When the film first came out, being the right age (an advanced 13) helped with one's appreciation of the troupe’s lunatic clomping over the Scottish Highlands. If you can regress far enough, you’ll probably still find several bits just as funny: “It’s just a flesh wound,” etc.
Step Brothers (2008)
Director: Adam McKay
Cast: Will Ferrell, John C. Reilly, Mary Steenburgen
Utterly infantile (and a stealth masterpiece of cringe comedy), this suburban fable about a pair of tantrum-throwing boy men has been gaining ground as presciently Trumpian. Sure, there are 51 movies on this list, but there's always the option of watching this one 51 times. You will be better for it.
The Lobster (2015)
Director: Yorgos Lanthimos
Cast: Colin Farrell, Rachel Weisz, Jessica Barden
In a surreal edge-of-town hotel, it’s compulsory for singles to find a partner, under the watch of an oppressive staff. If you don’t within 45 days, you’ll be surgically turned into an animal of your choice (star Colin Farrell has already decided to be a lobster). This is a movie in quote marks, tongue-in-cheek storytelling that uses absurdity to hold a mirror to how we live and love.
Director: Jason Reitman
Cast: Charlize Theron, Patrick Wilson
Charlize Theron plays ‘psychotic prom queen bitch’ Mavis Gary in a black comedy that’s all the funnier for not being set at high school. It’s decades later, and Mavis heads back to her small suburban town with her sights set on her ex, Buddy (Patrick Wilson), undeterred by the fact that he’s married with a baby. Once again, Juno writer Diablo Cody and director Jason Reitman achieve a near-perfect balance between bitter laughs and insightful observation.