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The Big Sick

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Kumail Nanjiani and Emily V. Gordon turn their real-life trauma into a sweet and funny romantic comedy with The Big Sick. Kumail falls for Emily (Zoe Kazan), and then must deal with her family as well as his own career and commitment issues when she is suddenly struck with a mysterious illness.

Drinking Buddies

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A pioneer of the indie-film mumblecore genre, director Joe Swanberg levels up to work with bigger stars in Drinking Buddies, while maintaining his loose, improvised style. Olivia Wilde and Jake Johnson star as longtime friends who work at a brewery together and navigate their unspoken mutual attraction while in relationships with other people.

It’s a simple story that Swanberg fills with painfully real observations and amusingly awkward interactions, with the same ramshackle charm as his early micro-budget films.

Heathers

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The 1980s were a golden age for teen comedies. Heathers is the black sheep of that age, a dark comedy starring Winona Ryder as a miserable popular girl and Christian Slater as the outcast bad boy who romances her and then uses her to take revenge on their vapid classmates. It’s full of hilariously mean-spirited one-liners, offering a bracing take on the inanity of teenage life.

His Girl Friday

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Possibly the definitive screwball comedy of the 1940s screwball-comedy heyday, His Girl Friday is a dizzyingly paced romantic comedy with whip-smart banter between former spouses (and current co-workers) played by Cary Grant and Rosalind Russell. Grant’s newspaper editor and Russell’s star reporter are constantly at odds over their relationship and the story they’re covering, and those sparks eventually turn to a rekindled romance.

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Landline

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This 1990s-set comedy from 2017 often feels like it was made in the ’90s, with its warm, cluttered aesthetic and NYC indie-movie subject matter. Jenny Slate stars in Landline as a struggling journalist who moves back in with her family, including her parents (Edie Falco and John Turturro) and younger sister (Abby Quinn).

The movie is less about the main character’s quarter-life crisis and more about the family’s messy but relatable squabbles. Slate is funny but also vulnerable, and the sibling bond between her and Quinn forms the movie’s charming emotional core.

The Lost City

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Sandra Bullock and Channing Tatum have excellent chemistry in throwback adventure comedy The Lost City. Bullock plays a jaded romance novelist kidnapped by a deranged billionaire (Daniel Radcliffe) who’s convinced that she knows the location of an ancient city full of riches. Tatum plays the beefcake cover model who decides he can come to the author’s rescue, despite knowing nothing about wilderness survival or covert operations.

The two characters amusingly bumble through the jungle, bantering and bickering on their way to predictable but satisfying romance.

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Love & Friendship

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Writer-director Whit Stillman adapts Jane Austen’s early, lesser-known novel Lady Susan as Love & Friendship, a tart comedy about social climbing and romantic scheming. Kate Beckinsale gives one of her best performances as the conniving Lady Susan, who is always quick to deliver a withering putdown, and the tone is sharper and more cutting than a typical Austen adaptation.

My Man Godfrey

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In the midst of the Great Depression, Hollywood movies provided audiences with an escape, but My Man Godfrey derives its comedy from the Depression itself. The movie doesn’t downplay the seriousness of poverty, and it uses the upper-class Bullock family to poke fun at entitled privilege amid societal misfortune.

William Powell plays the title character, a “forgotten man” who becomes the Bullocks’ butler and falls in love with Irene Bullock (Carole Lombard). Godfrey turns the situation to his own advantage, proving smarter and more resourceful than the wealthy people who see him as an object of pity.

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Superbad

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Screenwriters Seth Rogen and Evan Goldberg were inspired by their own lifelong friendship when they came up with Superbad, and that bond shines through. Jonah Hill and Michael Cera play the fictional versions of Seth and Evan, on a single epic night at the end of their senior year of high school. The characters go on a ridiculous odyssey in their efforts to obtain alcohol for a party, with plenty of hilarious mishaps.

Superbad balances its raunchy humor with a surprisingly sweet dynamic between the main characters, whose friendship proves stronger than any adolescent urges.

Zoolander

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Ben Stiller took a silly character created for sketches on the VH1 Fashion Awards and turned him into a pop-culture icon with Zoolander. Stiller’s title character is a vapid but “really, really ridiculously good-looking” male model who becomes embroiled in a plot to assassinate the prime minister of Malaysia.

Owen Wilson plays Zoolander’s fellow model and frenemy Hansel, with Will Ferrell as the evil fashion designer behind the conspiracy. The movie is full of celebrity cameos and quotable lines, with a perfect mix of cleverness and camp.