There are several films that have challenged the culture of masculinity but two films I’ve seen have done it well without being overly heavy handed and preachy. Both of them were made almost six decades ago.
The Swimmer (1968)
Burt Lancaster plays Ned Merrill, a middle aged man who lives in an affluent suburb in Connecticut and on a fine sunny day decides to create an odyssey for himself by swimming in all the neighboring pools that leads to his home.
Without giving away too much of the story and characters, Ned is an engrossing representation of post WW2 masculinity. With his 1000 watt smile, stamina, tall, athletic physique and charm he believes he can get away with what is essentially discourtesy and trespassing with his strange mission. However he wins over many of the people he encounters through his childlike idealism and confidence. In contrast, the latter portion of the movie demonstrates that he may not be the person that projects himself to be.
Ned Merrill represents a reevaluation of the idiosyncratic, go-getting, salesmanesque persona that resonated in the 1950’s up into the early 60’s. He is a representation as well as a deconstruction of the ideal ‘from nothing to something’ man who compartmentalized his more tender emotions and adopted a smiling yet secretly ruthless and exploitative persona that although it appealed to the masses, his bank account and social standing, it wore away at his integrity and morality.
The Swimmer is a sad lesson to men who believe that they can find success in the world, not just by fooling others but by fooling themselves.
Five Easy Pieces (1970)
Jack Nicholson portrays Robert Dupea, a classically trained pianist from an upper class family who is determined to spend his life in a meaningless existence as he changes blue collar jobs just as often as he changes women. He is invited by his family to visit his dying father and takes along his pregnant waitress girlfriend whom he long had intentions of dumping.
Robert Dupea represents the infamous wanderer/rolling stone persona that was a source of both fascination and scorn in the 20th century. In Robert’s case he ironically comes ‘from something to nothing’ as compared to Ned. He has the talent to make something of himself but chooses not to. He is beloved by the comrades he meets on his journey but brings nothing but misery to those who want to get attached to him.
Whereas Ned is optimistic and ambitious Robert is boorish and cynical, climbing down the ladder of success fueled by an inexplicable disdain towards conventionality and responsibility. Ned is a tragic figure to watch whilst Robert is a miserable one.
Ned is a lesson in self-delusion.
Robert is a lesson in (the lack of) self-discipline.
I honestly believe that both films offer a revisionist perspective of what was accepted as masculinity in that mid 20th century era. Behind the facade of swagger and charisma were two broken men who were slowly destroying themselves and the people who loved them. For that reason I think both films are a must see for every man interested in analyzing himself at a deeper level.
Edit: Some commenters are assuming this answer as some sort of progressive, ‘toxic masculinity’ apology.
I am not a progressive, nor is this answer political in the modern sense (both movies were made almost six decades ago) and toxic masculinity is a term that I’m not an advocate for. Both films are character studies of flawed men of a flawed generation and every generation has its flaws.