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Tiffany Haddish’s big year included her turn in “Girls Trip” and a best-selling book. Credit Michele K. Short/Universal Pictures, via Associated Press

Jimmy Kimmel’s heartfelt monologue about health care; Louis C.K.’s apology for sexual misconduct; Kathy Griffin’s faint at the end of a two-hour-plus set after describing how a Trump joke gone awry put her on the no-fly list.

The most memorable moments of the year in comedy were not funny, which is only one of the seeming paradoxes of 2017. Comedians loomed large in popular culture, the tip of the spear in the daily response to the first year of a new presidency, and yet there were strong signs that the boom is on the verge of busting. Netflix reinvigorated the stand-up special, but I’m skeptical that the streaming service’s output produced more classics than in previous years. It’s been a contradictory and uneasy 12 months, and this pointedly idiosyncratic list covers a few of the highlights.

BEST COMEBACK SPECIAL This is the year Netflix threw so much money around that star comedians who hadn’t released a special in ages returned. Jerry Seinfeld released his first in 19 years. Dave Chappelle put out two new hours after a 13 year-hiatus, and he unveils two more on New Year’s Eve — that’s four specials in a single year. But no one was funnier than Norm Macdonald, whose verbally dexterous “Hitler’s Dog, Gossip & Trickery,” his first special in six years, cemented his reputation as one of the best stand-ups alive.

BEST LIVE SET As soon as Leslie Jones stormed onstage at the Comedy Cellar in July, the room shrunk, her raucous energy and ferocious crowd work making you aware of the low ceilings and echoing acoustics. She ranted about sex, dished about her “Saturday Night Live” co-stars and insulted the patrons in the front row, staring them down during long dramatic pauses, ramping up the tension only to explode it with punch lines. She told some good jokes, but the best parts of this roughly 10-minute set were the riffing and the swagger that make live stand-up the most exciting art in the city.

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Bill Heath, left, and Nathan Fielder in “Nathan for You.” Credit Comedy Central

MOST HEARTBREAKING COMEDY For the last four seasons, “Nathan for You” has essentially been an inspired prank show with a mild-mannered consultant giving terrible advice to small businesses. Its star, Nathan Fielder, displayed hints of melancholy, but nothing prepared fans for his wrenching season finale, “Finding Frances.” It centered on a character from an earlier season, a Bill Gates impersonator named Bill Heath, whose lost love from childhood provides the central mystery. What went wrong? Could he get a second chance? Mr. Fielder traveled with Mr. Heath to Arkansas to track her down, while a parallel story involving Mr. Fielder and an escort he falls for, becomes an unlikely romance. The documentarian Errol Morris called it “my new favorite love story.”

What made this episode so affecting for me, however, was its portrait of Mr. Heath, who moved to Hollywood with dreams of show business that never panned out. His Bill Gates impression is terrible, and the comedy of his ineptness carries a hint of cruelty. There’s a long history of comedians using eccentric real people for morally questionable laughs, from Larry (Bud) Melman to the many characters in “Tim and Eric Awesome Show, Great Job!” “Nathan for You” is part of this tradition but transcends it, digging deeper, exploring Mr. Heath’s past, his family and politics with a sympathetic, sensitive and even humane eye, proving that anything in the world can be fascinating and complex if you look closely enough.

    BIGGEST BREAKTHROUGH On top of releasing a best-selling book and a special, the stand-up Tiffany Haddish did more than anyone to turn the big-screen comedy “Girls Trip” into a significant hit. When she visited the New York club Carolines recently, she pointed out Whoopi Goldberg in the audience and spoke of the inspiration of seeing her one-woman show. “She’s my real mama,” Ms. Haddish said to roars.

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    BEST TRUMP IMPRESSION One of the greatest episodes of “The Twilight Zone” imagines an impulsive, love-starved and all-powerful 6-year-old who keeps the adults around him on edge. “The President Show,” in which Anthony Atamanuik plays Donald J. Trump as an angry and easily distracted mean kid, is its comedic twin. Unlike Alec Baldwin’s version of the president on “Saturday Night Live,” Mr. Atamanuik’s Comedy Central parody never gets predictable. His voice and mood constantly shift, often dramatically, and watching him captures the anxiety of many who look at the leader of the free world and think: What will he do next?

    MOST RESONANT POLITICAL COMEDY It’s a safe bet that next year will bring a ton of comedy about the #MeToo moment, but even before The New York Times published its exposés of Harvey Weinstein and Louis C.K., Tig Notaro took on Louis C.K., her own producer, with a subplot in her amusing mosey of a series, “One Mississippi,” that had obvious echoes of the sexual misconduct allegations leveled against him.

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    John Mulaney, left, and Nick Kroll at the Independent Spirit Awards. Credit Kevork Djansezian/Getty Images for Film Independent

    BEST DOUBLE ACT John Mulaney and Nick Kroll delivered the funniest award-show monologue of the year at the Independent Spirit Awards, talking over each other as they argued about the way Warren Beatty smoked pot. “I bet Warren has a really expensive silver vape that looks like a pistol,” Mr. Mulaney said, to which Mr. Kroll responded, “Warren’s got one of those Altoids boxes filled with pre-rolled joints that Danny DeVito gave him.”

    MOST PROMISING FUTURE STAR Every year there are many debut specials with impressive jokes, but much rarer are new stand-up comics with great cartoonish physicality. Even though his special “There’s No Business Like Show Business” didn’t exactly go viral (it didn’t help that it was on the streaming service Seeso, rest in peace), Fahim Anwar’s set evoked the act-outs of Sebastian Maniscalco and even some of the flamboyance of Sacha Baron Cohen.

    Islamophobia | Fahim Anwar: "There's No Business Like Show Business" Video by slezdog2000

    BEST NEW IMPRESSIONIST Tyler Fischer’s Bill Burr is so good, I can’t listen to Bill Burr anymore without hearing it.

    BEST TAKE ON MORTALITY There was no better old-guy joke than the one in Marc Maron’s special “Too Real.” Talking about his anxiety at seeing the Rolling Stones in concert (“I just didn’t want it to be sad”), he finishes up by describing the triumph of leaving early to beat the crowd.

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