Predicting The 2021 Emmy Award Winners: Outstanding Drama/Comedy Guest Actor & Actress

By Amanda Spears ​

The Creative Arts Emmys are being held this weekend and as I've been doing Outstanding Comedy, Drama, Limited Series/TV Movie Writing, and Directing & Casting, I'm going to take you television fans through how to make your Emmy predictions and win your pool. Next up is Outstanding Drama/Comedy Guest Actor and Actress. If you remember from last year in my Golden Globe, SAG Awards, and Oscars predictions, I try (my best) to leave emotion out of making my predictions. Six years ago, the Emmys moved to a plurality vote replacing the more-level playing field of 80-100 person panel's ranking the nominees. Since we spend more time watching television than a film, it's easier to let our personal preferences affect our predictions as we try to manifest a win for our favorites.

The acting categories are where stats can only take you so far – instinct and buzz also matter. If there are categories on the Drama and Comedy side where anything can happen this year, it's the Outstanding Drama/Comedy Guest Actor and Actress races. Hollywood A-listers and working actors make these difficult to predict. Let's take a look at how to predict the winners for Outstanding Drama/Comedy Guest Actor and Actress based on recent trends starting with the Drama categories.

Outstanding Guest Actor in a Drama Series Nominees
Don Cheadle - "The Falcon and the Winter Soldier"
Charles Dance - "The Crown"
Timothy Olyphant - "The Mandalorian"
Courtney B. Vance - "Lovecraft Country"
Carl Weathers - "The Mandalorian"

Outstanding Guest Actress in a Drama Series Nominees
Alexis Bledel - "The Handmaid's Tale"
Claire Foy - "The Crown"
Mckenna Grace - "The Handmaid's Tale"
Sophie Okonedo - "Ratched"
Phylicia Rashad - "This Is Us"

Since 2017 on the Drama side and 2018 on the Comedy side, we have seen a dominance of the performers from nominated series winning the acting Emmys except for "Saturday Night Live" on the Comedy side and "The Handmaid's Tale's" hanging episodes in 2019. Then last year, on the Drama side, three of their six acting winners were from non-nominated series. But if you look at the 42 acting awards handed out (in the time frame above), that gives a performer from a nominated series still a 92% chance of winning. This leaves us with…

Outstanding Guest Actor in a Drama Series Nominees
Charles Dance - "The Crown"
Timothy Olyphant - "The Mandalorian"
Courtney B. Vance - "Lovecraft Country"
Carl Weathers - "The Mandalorian"

Outstanding Guest Actress in a Drama Series Nominees
Alexis Bledel - "The Handmaid's Tale"
Claire Foy - "The Crown"
Mckenna Grace - "The Handmaid's Tale"
Phylicia Rashad - "This Is Us"

Next to be eliminated are those who've made headlines for the wrong reason, leaving…

Outstanding Guest Actress in a Drama Series Nominees
Alexis Bledel - "The Handmaid's Tale"
Claire Foy - "The Crown"
Mckenna Grace - "The Handmaid's Tale"

It's a shame for Rashad, who's still looking for her first Emmy—without the controversy, she would've been formidable to challenge for the trophy.

Next, let's eliminate those that do not have the momentum or episode to challenge the top prize. Leaving…

Outstanding Guest Actor in a Drama Series Nominees
Charles Dance - "The Crown"
Timothy Olyphant - "The Mandalorian"

Outstanding Guest Actress in a Drama Series Nominees
Claire Foy - "The Crown"
Mckenna Grace - "The Handmaid's Tale"

Of those eliminated, Bledel, a past winner in this category (2017), has the best chance to do so and could follow Patricia Clarkson's awards trajectory winning for "Six Feet Under" (2002 and 2006). Weathers has very little to do in his episode and, unfortunately, will likely leave empty-handed.

Final Outstanding Guest Actor in a Drama Series Predictions
1. Timothy Olyphant - "The Mandalorian"
2. Charles Dance - "The Crown"
3. Carl Weathers - "The Mandalorian"
4. Courtney B. Vance - "Lovecraft Country"
5. Don Cheadle - "The Falcon and the Winter Soldier"

Final Outstanding Guest Actress in a Drama Series Predictions
1. Mckenna Grace - "The Handmaid's Tale"
2. Claire Foy - "The Crown"
3. Alexis Bledel - "The Handmaid's Tale"
4. Sophie Okonedo - "Ratched"
5. Phylicia Rashad - "This Is Us"

And then there were two. Can Foy rule once again, or will Grace walk away victorious? "The Handmaid's Tale" has had a stranglehold on this category, winning three of the past four years: Bledel (2017), Samira Wiley (2018), and Cherry Jones (2019). Since the category was Outstanding Guest Actress in a Drama Series, who was the youngest winner? If your answer was Bledel at age 35, you would be correct. Grace would smash this record at just 15 years of age, but the Emmys have a nasty habit of not awarding child and teen performers. However, Grace gives the most buzzed-about performance in the category. In her submission for the series opener "Pigs," she shows skills beyond her years as she balances being a victim of Gilead and a mini-Serena Joy. Helping Grace's case is her work in films "Gifted," "I, Tonya," and television "Young Sheldon," not to mention she appears to have more to do in "The Handmaid's Tale" upcoming fifth season. Foy is a past winner in Outstanding Lead Actress in a Drama Series (2018). In her submission "48:1," she reprises her role as the then Princess Elizabeth II giving her famous Commonwealth Speech and setting up the conflict between present-day Queen Elizabeth II (Olivia Colman) and Prime Minister Margaret Thatcher (Gillian Anderson). But that is all Colman does—recites a speech that doesn't give her the chance to emote, which could provide Grace her opportunity at a record that may never be broken.

On the gentleman's side, we have Olyphant and Dance. Dance, a "Game of Thrones" alum, received his fourth nomination for his performance as Lord Mountbatten in the series opener "The Gold Stick." While his character's (real-life) untimely death does get the action going in season four, his main contribution is two-fold: a narration of a letter and his death. Like Foy, he doesn't really have a lot to do. But if this was not enough of a problem, this category tends to favor home-grown actors as Patrick McGoohan ("Columbo") 31-years ago was the last British-American to win. And while the Emmys have definitely become more international, it is worth noting that there have been several international nominees in the past 31-years unable to win this category. This leaves the door open for Olyphant on his third nomination for "The Mandalorian's" series opener "Chapter 9: The Marshall." Unlike Dance, Olyphant is front and center throughout his episode as "The Marshall," using a Mandalorian suit to protect a small galactic town. Considering Olyphant's past work in cult-favorites "Justified" and "Deadwood," this could be a good time for his fellow actors to award him for what he does best.​

And now we move over to the Outstanding Comedy Guest Actor and Actress races...

Outstanding Guest Actor in a Comedy Series Nominees
Alec Baldwin - "Saturday Night Live"
Dave Chappelle - "Saturday Night Live"
Morgan Freeman - "The Kominsky Method"
Daniel Kaluuya - "Saturday Night Live"
Daniel Levy - "Saturday Night Live"

Outstanding Guest Actress in a Comedy Series Nominees
Jane Adams - "Hacks"
Yvette Nicole Brown - "A Black Lady Sketch Show"
Bernadette Peters - "Zoey's Extraordinary Playlist"
Issa Rae - "A Black Lady Sketch Show"
Maya Rudolph - "Saturday Night Live"
Kristen Wiig - "Saturday Night Live"

Since 2018, on the Comedy side, the series has to be nominated if the actors are going to win anything, with the exception of "Saturday Night Live." This narrows the field down to...

Outstanding Guest Actress in a Comedy Series Nominees
Jane Adams - "Hacks"
Yvette Nicole Brown - "A Black Lady Sketch Show"
Issa Rae - "A Black Lady Sketch Show"
Maya Rudolph - "Saturday Night Live"
Kristen Wiig - "Saturday Night Live"

I'm not comfortable eliminating one sketch show's nominees and leaving another's, so for now, this saves the ladies of "A Black Lady Sketch Show." Sorry, Bernadette, it's not "Rose's Turn" this time—but thanks for playing. Next, let's eliminate the nominees who got in on sheer extraneous momentum but lack the episode to be formidable. Let's also eliminate any surprise nominees. Leaving the state of the race as…

Outstanding Guest Actor in a Comedy Series Nominees
​Dave Chappelle - "Saturday Night Live"
Morgan Freeman - "The Kominsky Method"

Outstanding Guest Actress in a Comedy Series Nominees
Jane Adams - "Hacks"
Issa Rae - "A Black Lady Sketch Show"
Maya Rudolph - "Saturday Night Live"

Sorry Baldwin, your Trump may have won Supporting Actor four years ago (2017), but it's hard to see another win in his future. Kaluuya and his recent Oscar win ("Judas and the Black Messiah") helped him crack into this race, but if Brad Pitt similarly couldn't win here last year—Kaluuya's probably not either. Like Phoebe Waller-Bridge the previous year, Levy probably rode a wave of residual goodwill to crack the lineup. Meanwhile, Wiig is a perennial nominee and doesn't have the buzz to win—here's hoping her time's coming maybe on one of her fellow SNL Alums shows. And it was just great to see Brown amongst the lineup but here's hoping she'll get another chance at victory.

​Final Outstanding Guest Actor in a Comedy Series Predictions
1. Chappelle - "Saturday Night Live"
2. Morgan Freeman - "The Kominsky Method"
3. Daniel Levy - "Saturday Night Live"
4. Daniel Kaluuya - "Saturday Night Live"
5. Alec Baldwin - "Saturday Night Live"

Final Outstanding Guest Actress in a Comedy Series Predictions
1. Jane Adams - "Hacks"
2. Maya Rudolph - "Saturday Night Live"
3. Issa Rae - "A Black Lady Sketch Show"
4. Kristen Wiig - "Saturday Night Live"
5. Yvette Nicole Brown - "A Black Lady Sketch Show"
6. Bernadette Peters - "Zoey's Extraordinary Playlist"

How much of a hurdle is Levy to Chapelle? Chapelle won this race in 2017 but also faced multiple SNL hosts like the always-popular Tom Hanks and Lin Manuel-Miranda right off of "Hamilton." But including Chapelle, there were only three out of six nominees. Can Chapelle win when "SNL" makes up four of the five nominees? Enter living legend Morgan Freeman—believe it or not, this is his first-ever acting Emmy nomination, and while he doesn't have a lot to do in his episode on "The Kominsky Method," that's never stopped the television academy in the past (i.e., Margo Martindale, "The Americans").

Can Rudolph make history as only the second woman to win this category in consecutive years? Only Jean Smart has been able to do so for "Frasier" in 2000-2001. Helping Rudolph is her much loved and buzzed-about performance as Vice President Kamala Harris. Who wins, if not Rudolph? Enter Adams, a character actress that has been working on television for years in everything from "Hung," "Twin Peaks," and "Sneaky Pete," just to mention a few. In one of the front-runners to win Comedy Series, Adams gives a frazzled sympathetic performance in the series finale. Should Adams, Rae, or Brown win, they would make history as the first to do so for an HBO Series. I'm going with the character actress—where Adams will make HBO history.

Do you agree or disagree with my logic? What are you predicting to win the Emmys for the Outstanding Drama/Comedy Guest Actor and Actress categories? Let us know your thoughts in the comments section below or on our Twitter account. Stay tuned for more articles on the Emmys as I finalize my predictions for the 2021 Emmy Awards taking place on September 19th.

You can follow Amanda and hear more of her thoughts on the Emmys and TV on Twitter at @msamandaspears