20. But I’m a Cheerleader
There is a large cult following for this LGBTQ+ satire, where Megan (Natasha Lyonne) is castigated and sent to a pray-the-gay-away camp out of fear that she may be – gasp – queer. It is viciously colourful in its appearance, as if it were influenced by a campy John Waters film. Its comedic nature is almost entirely sarcastic, as if there is a lot of truthful hurt underneath the jokes that many members of the LGBTQ+ have had to face for centuries.
Despite being released at the tail end of the 20th century (in 1999), But I’m a Cheerleader is a progressive film that faced much backlash initially for being both a pale imitation of other queer films and a stereotype of itself. Now, the film is being more realized as a misunderstood statement, where the fun and the agony are one in the same.
19. Me Without You
“[Williams] is terrific in what could become her breakout role from television’s Dawson’s Creek” wrote critic Gerry Shamray in response to the talent Michelle Williams injected into her work in Me Without You; and so it begins. This drama pit Williams up against Anna Friel as two best friends whose separate personal lives affect their own relationship together.
If there’s anything substantial to get out of this, it’s the contrast and connection both Williams and Friel have with one another, which is the centrepoint of this film after all. Aside from that and the heightened melodrama, there isn’t too much here but a bright sign that more was to come from Michelle Williams.
18. Suite Française
Every performer has to do one epic romance, right? For Williams, it’s the period piece Suite Français, as she co-stars with Mattias Schoenaerts, Kristin Scott Thomas, and Margot Robbie, amongst others.
Taking place in German-occupied France, this is the tale of waiting for a loved one, whilst falling for the enemy (the French Lucille, Williams, and the German Falk, Schoenaerts). It’s a tale we’ve heard before but told differently, yet it excels in the passion that the leads, production, and aesthetics put forth. The love can be felt, and it surpasses any of the major flaws Suite Français might have.
17. Wonderstruck
While Wonderstruck might be style over substance (a curious problem to have with a family, no, childhood drama), its title might be one of the sensations you feel while watching it. Williams is teamed up with adults Julianne Moore and Tom Noonan, plus a couple of standout child performances.
These roles take place within two different but thematically interconnecting stories of children searching for what home means for them (in the form of a guardian they have been separated by). Wonderstruck is a mature spectacle of a story embedded in childhood, and it has since resonated with some viewers more than others (maybe I am lumped in that former category).
16. Lassie
Well, duh, which ‘90s kid didn’t grow up on Lassie? This adaptation of the beloved ‘50s canine is, well, one of the finer live action children films to feature animals in the 1990s, but that really isn’t saying much (remember Dustin Checks In? See what I mean?). It’s no Babe, sure, but it’s fairly inoffensive considering.
Plus, it gave us the very first film performance of Michelle Williams as April Porter: a young student who has eyes on fellow classmate (and starring child role) Matt (also the owner of the titular canine). Lassie won’t be anything to write home about if you haven’t seen it before, but there will be a very small place for it in the hearts of those that grew up on it. Moving on.
15. Shutter Island
We’ve reached the top 15: the films I consider the best starting points for anyone new to the works of Michelle Williams. Shutter Island might have been very predictable and with a bit of a cop-out of an ending, but Martin Scorsese’s psychological thriller still has a lot of interesting stuff going on. The effects – caused by a fragmented mind – are quite sensational.
The elements of noir tossed in make Shutter Island feel like an unreliable narration by a detective that means his best. Williams plays Dolores, wife of Teddy (Leonardo DiCaprio), and his memories of her play like never-ending nightmares. Williams brings a certain authenticity to this role, and it makes Teddy’s anguishes hurt all the more for us.
14. Land of Plenty
The works of Wim Wenders might be a bit hit and miss lately (Pina being a definite hit, for instance), and Land of Plenty might fall under this same indecisive spell. When it comes to its nature, Land of Plenty is a strong effort full of emotions and commitment.
There might be a slight preachiness to the story, but it shows shimmers of powerful moments; many of these instances emanate from Williams’ graspable performance as the charitable Lana. Land of Plenty is a forgotten film that is worth a shot for the moments that do work.
13. All the Money in the World
This Ridley Scott film, infamous for its post-production and last minute shoots to erase Kevin Spacey’s portions of the film, was actually quite good considering. Even with the quick implementation of Christopher Plummer (which was good enough for an Oscar nomination) and Scott’s flimsy reliability in recent years, All the Money in the World is a solid thriller that is heavily anchored by Williams’ take on Gail Harris.
As a mother that yearns to be strong but gets sent into occasional spirals during a crisis, Williams is a commanding soul that Plummer’s greed and Mark Wahlberg’s faithfulness swirl around.
12. Dick
Nineteen years after Andrew Fleming’s political comedy Dick first came out, it might be worth considering giving the film another whirl. In context, Williams and Kirstin Dunst are two dimwitted teenagers that accidentally get wound up in the unveiling of the Watergate scandal that ultimately ended Richard Nixon’s run as president of the United States.
Okay. In hindsight, it’s even funnier knowing the heavyweight work and prestige these two actresses carry now; imagine revisiting them in this cheeky, goofy satire. Dick is a ‘90s relic that somehow still works (and not through nostalgia alone).
11. Wendy and Lucy
I never quite realized how many films Michelle Williams shared with other species of the animal kingdom, but compiling this list has made me very aware of this fact. Wendy and Lucy is a finer example of Williams acting alongside an animal; this time it’s the dog Lucy (bet you can’t guess Williams’ character’s name).
This is a gripping tale of what an owner is willing to do for their faithful companion, and it certainly doesn’t pull any punches. Sacrifice after sacrifice, mistake after mistake, Wendy and Lucy is a tear jerker that places Williams at the forefront for the world to witness her ability to move you. Be ready to bawl, though.