2020 Emmy Predictions: Best Guest Actor and Actress in a Drama and Comedy Series

Best Guest Actor in a Drama Series

Will Win - Giancarlo Esposito "The Mandalorian"

Could Win - James Cromwell "Succession" or Andrew Scott "Black Mirror" 

Should Win - Cromwell

Commentary - Andrew Scott didn't win last year, but he got a lot of buzz for his role in Fleabag, many claiming he was robbed. Can that translate to an Emmy win this year? Maybe, but Black Mirror has declined tremendously in terms of quality, so if he wins it is on his name alone. James Cromwell is grumpy and great in Succession, and could be swept up in the show's popularity. But I am going out on a limb for Giancarlo Esposito. He is a double nominee this year, and the only acting nominee from The Mandalorian, which got a shocking Drama Series nomination. We know it is going to win some Emmys, and with that much popularity, and his personal popularity among actors, I think he can pull off an upset. 

Best Guest Actress in a Drama Series

Will Win - Cherry Jones "Succession"

Could Win - Cicely Tyson "How to Get Away with Murder" 

Should Win - Tyson or Rashad

Commentary - I would love to see Tyson finally win for her excellent role in HTGAWM, and I would also like to remind Emmy voters that they have never rewarded Phylicia Rashad. But after winning last year for The Handmaid's Tale, and having a standout roll in Succession, which is this year's biggest Drama Series, will earn Cherry Jones another Emmy. 

Best Guest Actor in a Comedy Series

Will Win - Eddie Murphy "Saturday Night Live"

Could Win - Luke Kirby "The Marvelous Mrs. Maisel" or Fred Willard "Modern Family"

Should Win - Murphy

Commentary - Eddie Murphy's triumphant return to SNL should easily win this category. But there are three SNL guys, last year's winner Luke Kirby, and the late great Fred Willard for his great role in Modern Family. So it is not a slam dunk.

Best Guest Actress in a Comedy Series

Will Win - Wanda Sykes "The Marvelous Mrs. Maisel"

Could Win - Maya Ruldolph for either SNL or The Good Place or Phoebe Waller-Bridge "Fleabag"

Should Win - Angela Bassett "A Black Lady Sketch Show"

Commentary - Phoebe Waller-Bridge could have lingering love, and Maya Rudolph has two excellent chances to win. But I think that her votes will split, and I think Wanda Sykes, who has been nominated a lot recently, playing the great Moms Mabley will be a lot like Luke Kirby playing Lenny Bruce, and earn her an Emmy.