Angela Bassett as Mo, A Black Lady Sketch Show (Angela Bassett Is the Baddest Bitch)
Bassett has five previous nominations, including a bid in this category from 2017 for “Master of None,” and she also contends this year for narrating “The Imagineering Story.” Her guest spot in the pilot episode of the HBO variety series is brief, but its significance is clear from her name being in the title. I don’t think it compares to her previous work, but evidently she’s popular enough that even a few minutes in a short sketch is enough to merit a nomination.
Bette Midler as Hadassah Gold, The Politician (Vienna)
This is Midler’s fifth acting bid. She previously won trophies for performing in her “Diva Las Vegas” concert in 1997, an episode of “The Tonight Show with Johnny Carson” in 1992, and producing a music special in 1978. She was expected to be here along with costar Judith Light, who was snubbed, and Midler will definitely benefit from her one-episode appearance in season one leading into a regular role in season two, which debuted this June. Not having to compete with Light, whose campaign Midler’s Gold manages, she has a much better shot. It’s an energetic performance but it doesn’t help that her show didn’t earn any other major nominations.
Maya Rudolph as Judge Gen, The Good Place (You’ve Changed Man) and as Kamala Harris, Saturday Night Live (Host: Eddie Murphy)
Thanks to recent rule changes that made such things possible, Rudolph becomes the first performer ever to earn two separate nominations in a guest category. This is Rudolph’s third consecutive bid for “The Good Place” and her second for “Saturday Night Live.” She’s terrific in her submitted episode for NBC’s departed comedy series, humorously detailing her observations on (and plans for) humanity, but I don’t think that will compare to the incredible timing of her extended cameo as Kamala Harris being eligible for voting just days after she was announced as the Democratic vice-presidential candidate. Like guest actor nominee Brad Pitt, it’s not really substantial compared to other performers in this category – or even her role as the judge – but she does do a great job and I think it’s exactly what voters are looking for now.
Wanda Sykes as Moms Mabley, The Marvelous Mrs. Maisel (A Jewish Girl Walks Into the Apollo)
Sykes has been nominated in this category twice before, in 2017 and 2018, for “Black-ish.” She won as part of the writing staff for “The Chris Rock Show” in 1999 and contends this year both as a producer for “Tiffany Haddish: Black Mitzvah” and her voice-over work for “Crank Yankers.” Sykes in nominated here for playing another famous and trailblazing comedienne, and she gets to deliver some of her material in the season finale of her show. This isn’t like much of Sykes’ past work and could very much impress voters.
Phoebe Waller-Bridge as Various Characters, Saturday Night Live (Host: Phoebe Waller-Bridge)
Waller-Bridge was a fixture of last year’s Emmy ceremony, claiming acting, writing, and producing prizes for “Fleabag.” This year, she’s back here and as a producer for “Killing Eve.” She does well enough as host, delivering a funny opening monologue and participating fully in sketches, but her work doesn’t hold a candle to what won her all those awards last year. I would have nominated her instead for her role on “Run.” Her nomination should be considered the product of residual enthusiasm and isn’t likely to result in a win.
Who should win (based on entire season): N/A
Who should win (based on individual episodes): Midler or Rudolph for “The Good Place”
Who will win: I think Rudolph has it in the bag for her Kamala impression, though maybe Bassett or Sykes could win too.
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