Best Guest Actor in a Drama Series
Will Win - Charles Dance "The Crown"
Could Win - Timothy Olyphant "The Mandalorian" or Courtney B. Vance "Lovecraft Country"
Should Win - Dance or Olyphant
Commentary - It would be great to see Timothy Olyphant win an Emmy, and Courtney B. Vance is good in Lovecraft Country. But I think the power of The Crown will lead Dance to his first Emmy Award.
Best Guest Actress in a Drama Series
Will Win - Mckenna Grace "The Handmaid's Tale"
Could Win - Alexis Bledel "The Handmaid's Tale" or Claire Foy "The Crown"
Should Win - Mckenna Grace "The Handmaid's Tale"
Commentary - Conventional wisdom suggests that this race is between Alexis Bledel and Claire Foy, as both women have won Emmys for these roles. And if people were to predict them, those are solid bets. I am going out on a limb for Mckenna Grace. She was a surprise nominee, meaning voters watched this season. If they watched this season and liked it, I think they will easily pick her.
Best Guest Actor in a Comedy Series
Will Win - Dave Chappelle "Saturday Night Live"
Could Win - Dan Levy "Saturday Night Live" or Morgan Freeman "The Kominsky Method"
Should Win - Dave Chappelle "Saturday Night Live"
Commentary - Dave Chappelle has dominated this category of late, and there is a good reason why. Every time he hosts SNL, he knocks it out of the park. I think he wins again. Dan Levy could still be on a high with voters after last year's Schitt's Creek sweep, and Morgan Freeman could benefit from a lot of vote-splitting.
Best Guest Actress in a Comedy Series
Will Win - Maya Rudolph "Saturday Night Live"
Could Win - Kristen Wiig "Saturday Night Live"
Should Win - Kristen Wiig "Saturday Night Live"
Commentary - On her 9th nomination, it is still amazing that Kristen Wiig has yet to win an Emmy Award. Unfortunately, she will have to sit out again. Luckily, it is to Maya Rudolph, who had a great hosting gig on SNL, and happens to be a friend of Wiig's.
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