My thoughts immediately jumped to The Homesman, an “unmarriable” woman in the wild west employs a drifter to help transport three women driven mad by frontier life to a church. It was excellent.
I feel like I get what you’re saying, but you might as well be describing Bridget Jones (which might count, for all I know). Not a virgin, but in her 30s, single, having trouble finding a relationship, a bit awkward, “Hollywood fat” (AKA “normal weight”), drinks (“Hollywood drunk” as in drinks a lot but only gets drunk enough to create comedic incidents to drive the plot), etc.
Maybe Wynona Ryder in “Girl Interrupted” where she’s in a mental institution.
Sandra Bullock in “28 Days” where her drinking causes her to be ostracized from pretty much everyone except her enabling douchey boyfriend?
“Byzantine” stars Gemma Arterton and Saoirse Ronan as mother/daughter vampires outcast from both human and vampire society.
I guess maybe I’m not clear if you mean “outcast” as “pathetic woman with problems” or just “lonely woman trying to get by”.
Consider me confused as well but would Australian comedy Muriel’s Wedding fit?
TCMF-2L
How about Gaslight? Granted she’s not single by either definition, but right from the moment she was married, she became more and more of an outcast and became more and more isolated as both she and the rest of the community thought she had a mental illness. As she would confide in people that she didn’t know what was going on, they’d write it off, just like you’d nod and smile as your neighbor with dementia tells you about the underpants gnomes that show up every night to steal his underpants.
Suddenly, Last Summer might work as well. About a woman that was traumatized by her cousin’s death. However, instead of helping her to work through the trauma, they force her to suppress it, to the point that they end up institutionalizing her both because she’s going mad from the stress and just to keep her quiet (the family didn’t want people knowing how or why he died).
One of the threads that runs throughout Cat on a Hot Tin Roof works as well. Other than his father, Brick’s entire family really doesn’t like Maggie. Even Brick told her to go have an affair with someone. However, by the end he and Maggie kinda sorta patch things up.
I liked that movie, but haven’t seen it for so long. But I remember her either being with her family or her new friend.
“I haven’t listened to ABBA since I’ve met you!”
“Goodbye, Porpoise Pit!”
are a few things I remember, too… And the scary “I can’t feel my legs”
lol @ underpants gnomes
I see what you mean, but none of these women are physically alone - being the only one on the screen for a good amount of time. Time to reflect, time to ponder, etc… Getting to know a character when she is alone, because she’s herself - not putting an act at work, for example, because she’s not being watched.
Nomadland? Also, do horror films count, like Misery or Carnival of Souls?
I’m surprised no one mentioned “Nomadland” but I remember her being alone for a good amount of time in the beginning. I saw those others, too, but “Misery” is one I haven’t seen in 20 years. I’ve been wanting to see it again. I only remember her and James Caan.
I didn’t mention it in my OP, but drama is what I was getting at. Glad you posed that question.
Frances Ha?
I saw that about 3-4 years ago, and the only thing I remembered about it was that it was a new movie done in b&w 
In that vain, I like the 2011 movie, “Haywire”, with Gina Carano. She is an operative whose agency burns her and murders her love interest and only ally because they want her to be the “fall guy” for an off book operation that went sideways. The main character definitely fits the description of an outcast, and how she manages to resolve it all made for a good movie.
The feel-good high budget masterpiece Edna the Inebriate Woman.
For Todd Solondz, I’d rather go with Welcome to the Dollhouse.
Vera Drake
The Lady in the Van
May
Three Colors: Blue
Bagdad Cafe (1987, directed by Percy Adlon). On the whole, the female protagonists aren’t really alone or alienated, although they face plenty of loneliness and alienation along the way. What an extraordinary film and what an uplifting experience it was for me to see it again 30-something years later.
Jeanne Dielman, 23 quai du Commerce, 1080 Bruxelles
Although she has some people around her, Mildred in Three Billboards Outside Ebbing, Missouri is a pretty lonely figure.
TCMF-2L
The Effect of Gamma Rays in Man-In-The Moon Marigolds has both Matilda – a middle school outcast – and her single mother who is pretty much on her own, partly due to her own fault.
How about The Sterile Cuckoo? Liza Minnelli seems to be a clever free spirit in the beginning, and devolves into a lonely, clingy misfit who drives away her nice guy boyfriend.
The Prime of Miss Jean Brodie is another example of a seemingly well integrated personality coming apart.
When Charleze Theron “uglied-up” for Monster in 2003, it was hailed as courageous and unique. But only for its time. On TMC on Demand you could pull up Ingrid Bergman’s A Woman’s Face, which was remade by Hollywood with Joan Crawford. Olivia de Havilland did Snake Pit, and Eleanor Parker wasn’t afraid to get mussed up for Caged or The Man with the Golden Arm.
These were women from the Goddess era, but they weren’t worried about ruining their images then, or even later when they had to take parts as Psycho-biddies. It was the actresses during the Sexual Revolution who couldn’t compromise their sex appeal.
Sharon Stone’s character in “The Quick and the Dead” is mysterious, on a mission, keeps to herself.