A lot of times, thinking back on movies from older generations means grappling with just how problematic they are. Tons of "classics" from decades past, if you watch them now, turn out to be pretty sexist, racist, homophobic, transphobic, fatphobic, ableist, or otherwise completely outdated and offensive. It's nice to know we're better able to recognize these types of issues in film, but it also can feel sort of depressing to have to approach every older movie on guard for cringe-y problematic stuff. Fortunately, there are tons of movies that also offer a great surprise, with well-rounded, progressive characters that avoid stereotypes. There are honestly a lot of groundbreaking movies that were ahead of their time when it came to their portrayals of women.
Many of these movies on the list are notable because they tackle issues that were often ignored during the time they were made, or because they avoid the stereotypes that were common during those times. Oftentimes, the movies are groundbreaking in part because they center women's unique experiences. Women have been amazing, trailblazing forward-thinking figures in history for all of time, and that's something that the films below recognize either explicitly or more gently and subtly.
1'The Thin Man' (1934)
The Thin Man is one of many films starring the detective characters of Nick and Nora, who were husband and wife. Nora is sharp as a tack and demands just as much (and often more) respect than Nick.
2'His Girl Friday' (1940)
Investigative reporter Hildy Johnson has inspired generations upon generations of smart, savvy women, and this film from 1940 (!) never sells her short.
3'Harold And Maude' (1971)
The character of Maude, played by Ruth Gordon, is one of the most eccentric, progressive, and independent female characters to ever grace the screen. She lived through the Holocaust, defies stereotypes about age, and is always in control of her own life.
4'Women In Revolt' (1971)
This Andy Warhol and Paul Morrissey satire casts trans women as trans women (it stars Candy Darling, Holly Woodlawn, and Jackie Curtis), and examines the feminist movement. In 1971, it was ahead of its time in many ways.
5'Friday Foster' (1975)
Friday Foster, Pam Grier's talented fearless photojournalist turned gun-wielding badass, is one of the best and most groundbreaking of Grier's roles, as her character is completely in control and powerful even as she has to deal with the explicit sexism of her coworkers.
6'9 To 5' (1980)
This fantastic workplace satire, starring Jane Fonda, Dolly Parton, and Lily Tomlin, confronts sexual harrassment and misogyny head on. It was made in 1980, and it's depressing to think about just how much hasn't changed when it comes to patriarchal office politics.
7'Ladies And Gentleman, The Fabulous Stains' (1982)
Diane Lane shines as the awesome, fearless punk rock teenager Corinne Burns, who decides to start a feminist band in her dead end town and achieves massive success.
8'Born In Flames' (1983)
The most groundbreaking, progressive sci-fi movie you've never seen, 1983's Born in Flames tackles sexism, racism, homophobia and violence, and centers women of color.
9'Desert Hearts' (1985)
Desert Hearts was one of the first mainstream movies to feature a lesbian relationship storyline, and it feels authentic and lovely, avoiding gimmick or exploitation.
10'The Accused' (1988)
In The Accused (which was loosely based off of the rape trial of Cheryl Arojo), Jodie Foster's character is brutally raped and Kelly McGillis' character takes on her case, determined to bring about justice. Together, the stories of both women in the film, which is almost three decades old now, highlight the traumatic, uphill battle of trying to get justice for the horrific crime of rape in a patriarchal society.
Tracy Turnblad loves her body and knows she's foxy dreamboat who can dance with the best of them. This John Waters character has become an icon of body positivity.
12'Thelma And Louise' (1991)
This outstanding road movie and revenge film features two women character who have had enough and are no longer willing to tolerate any of the injustices of the patriarchy. They're strong, unapologetic, and ahead of their time.
13'The Silence Of The Lambs' (1991)
Jodie Foster's role as Clarice Starling in this horror-thriller is a masterful portrayal of a woman doing her best and holding her own in a very male-dominated field.
14'Daughters Of The Dust' (1991)
This film about a family of black women living on an island off the South Carolina-Georgia coast was the first feature film directed by an African-American woman to be released theatrically in the United States, and its characters embrace the traditions and spirituality of their African ancestors, while speaking Gullah creole throughout the film.
15'Fried Green Tomatoes' (1991)
Fried Green Tomatoes features a number of incredible, dynamic independent female characters — the film stars Kathy Bates, Jessica Tandy, and Mary Stuart Masterson, among others — whose friendship is at the forefront as they deal with abuse and constricting gender norms.
16'If These Walls Could Talk' (1996)
This groundbreaking movie told the story of three women characters (played by Demi Moore, Sissy Spacek, and Cher) in three different eras (1950s, 1970s, 1990s) who all deal with unplanned pregnancies.
Jodie Foster is really good at finding awesome, groundbreaking female characters. In Contact, she plays Dr. Ellie Arroway, a brilliant scientist who makes the first contact with aliens and has to fight a number of institutional forces.
18'But I'm A Cheerleader' (1999)
But I'm A Cheerleader is an amazingly savvy, nuanced teen satire of homophobic culture in an era of teen movies like American Pie, and it doesn't sacrifice respect for its awesome, lovable characters.
19'All About My Mother' (1999)
This Pedro Almodóvar film features a prominent trans character, Agrado, who is actually played by a trans woman, Antonia San Juan. That's groundbreaking when you think about how often trans characters are played by cis actors, and it's even more notable considering the film was released in 1999, almost 20 years ago, and we are still seeing the same casting problem today.
20'Legally Blonde' (2001)
It's hard to believe Legally Blonde is more than 15 years old, but when the movie came out, "chick flicks" were often horribly boyfriend-focused, and Legally Blonde's Elle Woods turned that stereotype on its head, delivering a warm, funny, and flat-out feminist celebration of female resilience.
Secretary's unashamed portrayal of an extreme BDSM relationship definitely made it groundbreaking, and telling the story from the perspective of Maggie Gyllenhaal's character Lee Holloway allows it to remain progressive and aware.
The awesome thing about this list is that it's nowhere near comprehensive, and it's always exciting to uncover movies from long ago that turn out to have amazing, rule-breaking portrayals of women.