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Pretty Woman is among the many movies about the world’s oldest profession that make it seem kind of glamorous. These movies don’t.

Klute (1971)

The first film in Alan J. Pakula’s Paranoia Trilogy — which also includes The Parallex View and All the President’s Men — this dark thriller stars Jane Fonda as Bree Daniels, who believes she’s being stalked by a deadly john. She works with a detective played by Donald Sutherland who of course thinks he can save her, in every sense.

Fonda (above) won her first Best Actress Oscar for playing Daniels, a complex character who initially seems to enjoy her job — except for the part of being stalked, of course.

Midnight Cowboy (1969)

The first and only film with an X rating ever to win Best Picture, Midnight Cowboy tells the seedy story of Joe Buck, a Texas boy who moves to the big city and dresses up as a cowboy to sell his wares. He falls under the shaky wing of Rico “Ratso” Rizzo, played by Dustin Hoffman, who gets to deliver the often-imitated line “I’m walkin’ here!”

Directed by John Schlesinger and written by Waldo Salt, the film is notable for its empathetic portrayal — especially by 1960s standards — of low-level street hustlers, and its willingness to just spend time with its characters without judgement or false moralizing.

There’s a long story behind the film’s rating, which was later changed to an R.

Leaving Las Vegas (1995)

At first, it seems like Mike Figgis’ drama is going to go along with the heart-of-gold trope as Elisabeth Shue’s Las Vegas sex worker, Sera (above), tries to save Hollywood washout Ben (Nicolas Cage) from his plan to drink himself to death. But then things get darker and darker, especially in a horrific scene in which Sera takes on multiple awful young clients.

Leaving Las Vegas is a sad, sad movie, but Shue imbues Sera with dignity and supreme likability throughout, even as her plans collapse — and she still holds onto her dreams.

Cage won a Best Actor Oscar, and Shue was nominated for Best Actress but lost to Susan Sarandon for her role in Dead Man Walking. Sarandon is great but Shue absolutely deserved to win for a harrowing, tough performance in one of the most bluntly sad movies about the oldest profession.

Monster (2003)

Charlize Theron played hard against type as she de-glammed for this searing, uncompromising Patty Jenkins film inspired by the story of real-life serial killer Aileen Wuornos.

Suggesting that Wuornos first descended into murder out of desperation, mental illness and self-defense, Monster makes you kind of sympathize with a serial killer — until you definitely don’t. Wuornos’ claims of self defense soon turn into empty justifications.

Theron deservedly won a Best Actress Oscar for the role.

Taxi Driver (1976)

The young Jodie Foster is heartbreaking as a child so caught up in street life that she doesn’t comprehend how horribly she’s being exploited by the smooth-talking Sport (Harvey Keitel) in this masterful collaboration between director Martin Scorsese and screenwriter Paul Schrader.

With Mean Streets, Taxi Driver is one of the best and most-imitated time capsules of 1970s New York City grime, and it’s a testament to the film’s narrative virtuosity that by the end we’re rooting hard for obvious psychopath Travis Bickle (Robert De Niro) to do what needs to be done.

De Niro and Foster were both nominated for Oscars in this, one of the most enduring and harrowing movies about sex trafficking.

My Own Private Idaho (1991)

A highlight of 1990s indie filmmaking, this Gus Van Sant drama follows narcoleptic hustler Mike (River Phoenix in one of the best roles of his too-short life) in a journey from Portland to Idaho to Rome with fellow hustler Scott Favor (Keanu Reeves).

The film is a very loose adaptation of Shakespeare’s Henry IV, and Reeves believed in Van Sant’s script so much that he rode over 1,300 miles by motorcycle to convince Phoenix to make the movie with him. Its one of the most even-handed movies about sex work to focus on men.

Requiem for a Dream (2000)

If you want to convince people not to do heroin, show them Requiem for a Dream, Darren Aronofsky’s brilliant but painful adaptation of Hubert Selby Jr.’s novel about people who turn to drugs to escape reality — and end up in a much worse place than they started.

Things turn out especially horribly for Marion Silver (Jennifer Connelly, above), whose despair culminates in a party scene you’ll wish you could forget.

Sin City (2005)

This early mostly black-and-white masterpiece, directed by Robert Rodriguez and Frank Miller based on Miller’s graphic novels, does nothing to minimize the struggles of the hardworking women of Old Town.

But it also stresses that pretty much all of them — including the very blue-eyed Becky (Alexis Bledel, above) — can very much hold their own.

When one would-be john Jackie Boy (Benicio Del Toro) pulls a gun on Becky, she intones: “Oh sugar. You just gone and done the dumbest thing in your whole life.” Then her reinforcements arrive and things go very badly for Jackie Boy and his boys.

Vivre Sa Vie (1962)

In 12 vignettes, Jean-Luc Godard directs his then-wife and muse Anna Karina in this tough drama about a struggling woman who works in a record shop, mourning her collapsing marriage and dreaming of stardom.

Instead, she descends into the world’s oldest profession, and things only get worse from there.

The film’s bittersweet title translates to “My Life to Live.”

Tangerine (2015)

Director and co-writer Sean Baker may be the greatest chronicler of modern-day hustlers, and Tangerine, shot on iPhones, is one of the best films of our relatively young century. It follows to transgender sex workers (Kitana Kiki Rodriguez and Mya Taylor) who stage a donut-shop confrontation with a cheating boyfriend.

Comic, tragic, totally empathetic and gorgeous throughout — especially the drive-thru carwash scene — Tangerine is also, according to Rotten Tomatoes, it’s No. 4 on the list of the best Christmas movies ever made.

The Florida Project (2017)

Sean Baker’s followup to Tangerine is another wild, brutally honest look at the life of a woman selling herself — one in perhaps even more desperate straits than the protagonists of Tangerine.

The film stars first-time actress Bria Vinaite as Halley, who works out of a cheap motel on the outskirts of Orlando’s magic kingdom as she tries to shield her daughter (Brooklyn Prince) from the hardship of her life and make their sad surroundings feel like the happiest place on earth.

Willem Dafoe (above, with Vinaite) earned an Oscar nomination for his role as motel manager Bobby, who doesn’t need money to have endless generosity. This is a real faith-in-humanity movie, even when things seem impossibly bleak.

Almsot every Sean Baker film is in some sense about the world’s oldest profession, including the next one on our list…

Anora (2024)

Baker’s 2024 story about a dancer and escort who finds herself in a relationship with a Russian oligarch’s son seems like a Pretty Woman fantasy — at first.

But then Ani, aka Anora, discovers some grim realities about her new beau’s life. The movie is somehow frank, suspenseful, very funny and deeply sad, all at once.

Anora cleaned up at the Oscars, winning Best Picture, Best Director for Sean Baker, Best Actress for lead Mikey Madison, and more. It also won the Palme d’Or at Cannes.

Jeanne Dielman, 23, Quai du Commerce, 1080 Bruxelles (1975)

If you’ve never heard of this film, you’re not alone — but film cognoscenti who took part in last year’s prestigious Sight and Sound poll declared it the greatest film of all time. You can decide for yourself next time you have three hours and twenty-one minutes to spare, because that’s the runtime of this French film, made by Chantal Akerman when she was just 25, about a widowed single mother who supports her son by entertaining male clients in her humble apartment.

Whether its the best movie ever made is up for debate (among those who’ve actually seen it, at least) but it’s one of the most remarkable movies about the oldest profession in the way it presents it, nearly 50 years ago, as just another job.

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