There’s always been something about When Harry Met Sally… that irks Peter Hawley.

Hawley, the deputy director of the Illinois Film Office, said there’s an inaccuracy in the 1989 film that only those familiar with Chicago would notice: driving directions that show the main characters near North Avenue on Lake Shore Drive even though they are supposedly leaving the University of Chicago, in Hyde Park, and heading south.

“Things like that drive Chicagoans crazy,” Hawley adds. But ultimately, for Hawley, “if they’re filming here in Illinois, it doesn’t really matter. It’s win-win for us.”

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Chicagoans love to see their city on the big screen, and when it comes to film and TV expenditures in Illinois, 2021 was “a record-breaking year,” Hawley said, with revenues totaling $630 million.

Hawley says such growth is courtesy of the state’s film tax credit, which went into effect in 2004, and the arrival of the production studio Cinespace in 2010.

Chicago is also a big, diverse city full of stories, said Ryan Oestreich, the general manager of the Music Box Theatre. “Chicago is not limited in its storytellers, or its backdrops. And I think that’s great for us as a city.”

For people immersed in the local film landscape, the action is really in the city’s “documentary energy,” said Anthony Kaufman, a senior programmer at the Chicago International Film Festival. “Chicago has a really strong social justice, social activism, political core to it.”

2022 in particular saw several films with Chicago connections generate buzz, from Jordan Peele’s Nope, which could be an Oscar contender (and has a local star) to documentaries such as Let the Little Light Shine that toured the festival circuit. To compile our must-watch list, WBEZ spoke with Chicago filmmakers, programmers and film executives — and did some of our own watching.

Note that some films aren’t yet available by streaming; for the ones that are, we’ve listed where you can watch them. Have a new release you’d suggest for our list? Tag us on social media or write us at web@wbez.org.

Punch 9 for Harold Washington (2022), directed by Joe Winston

Joe Winston’s documentary tells the story of Mayor Harold Washington and the election that won him the mayoral seat in 1983, making Washington the first Black mayor of Chicago. The captivating film premiered at the Chicago International Film Festival in October 2021 and screened at the Gene Siskel Film Center for one night only in September 2022 “to a packed house,” said Rebecca Fons, the director of programming at the Siskel.

“It’s a really fascinating portrait of a man, but also the time. A lot of what was going on when Harold Washington was running for mayor is the same as it ever was,” Fons said. “It really represents a lot of the politics that we’re dealing with now, and race relations in the city and the segregation of the city.”

Till (2022), directed by Chinonye Chukwu

Nearly seven decades after the Chicago youngster was lynched in Mississippi, Emmett Till’s story — and the story of his mother’s quest for justice — is told through Chinonye Chukwu’s poignant film.

The movie stars Jalyn Hall as Emmett Till, Danielle Deadwyler as Mamie Till-Mobley and Whoopi Goldberg as Till-Mobley’s mother, Alma, and features scenes of the Till family at home in Chicago. Ultimately, the movie highlights Till-Mobley’s powerful and tireless activism work. Deadwyler’s performance has been called “Oscar-worthy.” (Screening in theaters and streaming on Apple TV+ and Amazon Prime Video).

Rounding (2022), directed by Alex Thompson

Alex Thompson has been called one of Chicago’s up-and-coming moviemakers along with screenwriter and actor Kelly O’Sullivan. With screenings at the 2022 Chicago International Film Festival in October and as an online premiere at the Tribeca Film Festival, Rounding promises rich, psychologically wrought horrors. In this feature, a doctor (Namir Smallwood) becomes captivated with an asthma patient (Sidney Flanigan)’s particular case, while the doctor’s past begins to weigh on him.

Thompson’s sophomore film follows up on the successful release of Saint Frances (2019), a heartfelt drama and coming-of-age film. Shot locally, including at St. Vincent de Paul Catholic Church in Lincoln Park, the movie took home a jury prize and the audience award from SXSW in 2019.

Fire Island (2022), directed by Andrew Ahn

Joel Kim Booster wrote and stars in Fire Island, a romantic comedy that bills itself as a LGBTQ+ retelling of Jane Austen’s Pride and Prejudice.

And while the film is set on Fire Island in New York, Booster himself has strong Chicago roots, having worked as a standup comic and developing his comedic chops at local venues like Town Hall Pub. For Jack Smart of The A.V. Club, the movie is “As much a documentary-like depiction of the titular queer haven as it is a real-deal romantic comedy, Fire Island’s real love letter is to the experience that is Fire Island.” (Streaming on Hulu)

All Jacked Up and Full of Worms (2022), directed by Alex Phillips

Filmed almost entirely in Chicago, this movie is a “surreal, late night kind of film,” says Kaufman, a senior programmer at the Chicago International Film Festival. Describing the plot of the fictional, full-length movie All Jacked Up and Full of Worms doesn’t do the movie justice. It’s trippy, rich in psychedelic imagery and has a stream-of-consciousness feel — punctuated by lots of body horror and, well, worms.

It’s not for the faint of heart, but the movie — directed by Phillips, a Chicago-based filmmaker who cites body horror maestros like David Cronenberg as inspirations — drew a crowd at its October Music Box premiere.

Said Oestreich: “It was wild, there were like 500 people in attendance for the Chicago premiere for this tiny, tiny, tiny, independent movie probably made on a shoestring budget.” (Streaming on Screambox)

Let the Little Light Shine (2022), directed by Kevin Shaw

Shaw’s documentary centers on National Teachers Academy, a top-ranked predominantly Black elementary school on the South Side, and activists’ fight to save it from being shuttered between 2013 and 2014 during a wave of Rahm Emanuel-era school closings. Fons, the Siskel programmer, said her theater screened the film for a week — the minimum time required for a film to be eligible for an Academy Award nomination — with screenings featuring lively conversation and even a live set of music from the musician who scored it.

The film, which also screened as an official selection pick at the 2022 True/False Film Festival and was a SXSW EDU selection, resonated with audiences, Fons said. “There was a conversation every single night about this film, with packed audiences and people who’d been impacted by that time in Chicago and that effort by Rahm and the pushback. So it was great because it just felt like everybody knew the story, but they didn’t really know the story.” Fans of the film will have to wait until January 2023 to find out if it will be shortlisted for any Academy Awards. (Premieres nationally on PBS on Monday, Dec. 12)

A Compassionate Spy (2022), directed by Steve James

A Compassionate Spy takes viewers on a global journey with a distinctly Chicago fingerprint. The documentary, which has screened at festivals like the Telluride Film Festival and the Venice International Film Festival, feels both prescient and disarmingly intimate with its focus on the University of Chicago physics grad student Ted Hall and the relationship he had with his wife, Joan. It paints a nuanced portrait of Hall, who worked on the Manhattan Project in Los Alamos and gave intelligence to the Soviet Union.

First meeting at the University of Chicago, the couple navigated the tension of keeping Ted’s secret under wraps for decades. Longtime Chicago filmmaker Gordon Quinn, an executive producer on the film, describes it as “an epic love story.”

“We’re talking about the bomb and we’re talking about the threat of atomic warfare at the same time against the backdrop of this love affair and this great secret,” Quinn said.

Nope (2022), directed by Jordan Peele

Chicagoan Brandon Perea is among the stars of Jordan Peele’s latest movie, Nope. It draws from the very roots of cinema,referencing what is considered to be the first-ever motion picture: director Eadweard Muybridge’s short clip of a Black jockey, whose name is unknown, riding a horse. Peele’s new work blends together elements of science fiction and horror to create a movie that examines the very impulse to capture something on film. (Streaming on Peacock, Apple TV+, and Amazon Prime Video)