Who Will Win — And Should Win — The 2020 Emmys

Sunday, September 20th marks the 72nd Annual Primetime Emmy Awards, one of the first prestige awards shows, including the VMAs, to move forward after the onset of the COVID-19 pandemic. Naturally, there will be some noticeable differences — no red carpet, no live audience, and acceptance speeches will be broadcast live from winners’ homes. But with Jimmy Kimmel playing host for the third time this decade, we can at least count on a few familiar elements — even if the famous late-night personality is already planning for the night to be a “beautiful disaster.”

But in the end, it’s about the art anyway, right? Luckily, despite the pandemic’s lasting impact on the television industry as a whole, there are a sea of worthy contenders in competition this year. HBO’s phenomenal Watchmen has the most nominations of any series with 26 total, while Disney Plus is conquering its first Emmy season in a big way thanks to The Television Academy’s clear adoration of Star Wars spinoff The Mandalorian. There were some pleasant surprises, as well, such as Zendaya’s well-deserved nomination for Euphoria, some much-overdue love for Insecure, and an acting sweep from the cast of Succession.

Nevertheless, a nomination is not a win. Which is why we have put together a handy list for Emmy night, including our predictions for who will win in each of the major 16 categories as well as our picks for who should. Sometimes, those match up. Other times, they don’t. Read on to find out.

Outstanding Comedy Series

Who Will Win: Schitt’s Creek

Who Should Win: What We Do In the Shadows

For a while I had The Marvelous Mrs. Maisel in this spot. A huge-budget, hour-long Old Hollywood technicolor musical-cum-TV show that has already won in this category before seemed like a natural choice, especially considering The Television Academy’s affinity for repeat wins. But the more time passed, the more I realized that Schitt’s Creek is perfectly poised for an upset. The plucky Pop TV mainstay, which aired its heartwarming series finale earlier this year, took a while to gain traction with Emmy voters, but after its Thursday night win for Outstanding Casting, it’s clear that they finally have found something to adore about this hilarious gem. Nevertheless, I’m rooting for What We Do In the Shadows, a high-concept hangout sitcom about thousand-year-old vampires trying to blend in with their Staten Island surroundings. Already one of television’s funniest series during its first season, the show was even better in its sophomore year, a detail clearly seen through its three writing nominations.

Outstanding Lead Actor in a Comedy Series

Who Will Win: Ramy Youssef, Ramy

Who Should Win: Ramy Youssef, Ramy

Earlier this year, 29-year-old Ramy Youssef won a Golden Globe for his performance as the titular character in the first season of the Hulu dramedy about his life, leading to an acceptance speech that was both heartfelt (he began by thanking his god, Allah) and funny (“I know you guys haven’t seen my show,” he joked at one point). Not to imply that The Television Academy wants to copy the Hollywood Foreign Press Association, but after failing to nominate him for the show’s first season, it only seems right that they’d make up for it by actually letting him win this year. And with Youssef plunging even deeper into the fractured psyche of his protagonist this season, the win would be well-deserved. While he’s certainly competing against some tough competition (Ted Danson was a reliable scene-stealer in The Good Place and Schitt’s Creek would not function without the level-headedness Eugene Levy brings to an otherwise erratic cast of characters), Youssef is still the contender with the best shot.

Outstanding Lead Actress in a Comedy Series

Who Will Win: Rachel Brosnahan, The Marvelous Mrs. Maisel

Who Should Win: Catherine O’Hara, Schitt’s Creek

Like the show that turned her into a star, Rachel Brosnahan has always been an Emmy favorite who, it can be assumed, only lost last year because Fleabag proved such an unexpected breakout hit. Without that Amazon juggernaut standing in her way this year, though, I can see Brosnahan walking to an easy third win. Not that she should. With Schitt’s Creek officially off-air, this is The Television Academy’s last time to award Catherine O’Hara for her delightfully broad characterization of the wig-loving, weird-word-pronouncing, former soap star Moira Rose. The Emmys notoriously like to award comedies in the traditional sense and no nominee is more laugh-out-loud hilarious than Catherine O’Hara, who turned in a class-act bravura performance.

Outstanding Supporting Actor in a Comedy Series

Who Will Win: Mahershala Ali, Ramy

Who Should Win: William Jackson Harper, The Good Place

I love Mahershala Ali — like, love him — and I think he played a large role in the improvement Ramy made between its two seasons. As a funny, down-to-earth, rather unorthodox sheikh, Ali is impossibly charismatic. Throw in the fact that the actor won two Oscars over the course of three years and it’s hard to bet against him taking home his first Emmy come Sunday night. I certainly wouldn’t mind this outcome, but I’d personally prefer the award be bestowed upon William Jackson Harper, who has breathed necessary life into The Good Place’s most complex character, the ethics-obsessed Chidi Anagonye, ever since he stepped into the role in 2016. In its final season, Chidi was given more to do than ever before, and Harper always seemed ready to step up to the plate. While my feelings about the final season are complicated, there’s one thing I never doubted: William Jackson Harper is a bona fide star.

Outstanding Supporting Actress in a Comedy Series

Who Will Win: Alex Borstein, The Marvelous Mrs. Maisel

Who Should Win: D’Arcy Carden, The Good Place

While William Jackson Harper’s Chidi may have been The Good Place’s most complex character, it was D’Arcy Carden’s Janet that was always my favorite. Playing a robot (“not a girl”) that still feels human is decidedly tricky territory to traverse, and yet Carden never broke a sweat. (The fact that she was snubbed last year despite the incredible work she delivered in “Janet(s)" is one of the greatest travesties in television history.) But this is a scarily-stacked category: GLOW’s Betty Gilpin does consistently great work, Yvonne Orji has never been better than she is in Insecure’s fourth season, and Annie Murphy could nab the award just for her line delivery of “David” alone. But in the end, my money’s on Alex Borstein, who has won in this category twice before and whose performance is still key to Mrs. Maisel’s lasting appeal.

Outstanding Drama Series

Who Will Win: Succession

Who Should Win: Succession

Let me start off by addressing the elephant in the room: I’ve never seen Better Call Saul, a show I know many people (whose opinions I trust) adore and ostensibly would be rooting for. But that doesn’t stop me from asserting, in no uncertain terms, that this award belongs to Succession. A drama that often veers into the realm of straight-faced satire, Succession has been one of HBO’s largest recent success stories, a show many didn’t know what to do with in the beginning and now can’t get over. Judging by its bevy of acting nominations, it’s clear that The Television Academy counts themselves among this group. And with many of the other nominees — The Handmaid’s Tale, The Crown, and Stranger Things, particularly — maintaining their foot in the race solely on a technicality, I’d be willing to bet big bucks on Succession’s chances.

Outstanding Lead Actor in a Drama Series

Who Will Win: Billy Porter, Pose

Who Should Win: Jeremy Strong, Succession

The downside of having so many acting nominations is that, oftentimes, votes for your show can be split, ultimately canceling each other out. The probability for that is high in this category, as Brian Cox and Jeremy Strong’s respective performances as the egomaniacal oligarch of the Roy clan and his desperate-to-please son are the driving forces of the show. A vote split between the two would clear an easy path for Billy Porter, who’s already adored by The Television Academy judging by their decision to award him in this same category last year, when he was up against some of this competition (Jason Bateman and Sterling K. Brown). But as much of a soft spot as I have for Porter’s Pose performance, it’s Strong’s Succession story that has stuck with me most. Watching as Kendall grew from weathered, drug-addict failson to dad-stabbing power-player was fascinating, and Jeremy Strong sold every single second.

Outstanding Lead Actress in a Drama Series

Who Will Win: Jennifer Aniston, The Morning Show

Who Should Win: Zendaya, Euphoria

This award belongs to a person with one name: Zendaya. Of course, there’s a huge possibility that Zendaya’s young age (24) — and the fact that she’s playing someone even younger on screen (17) — will play to her disadvantage. The Television Academy doesn’t commonly award teen fare (hence the lack of Euphoria nominations in other categories, despite it operating on an HBO budget second only to Game of Thrones). But Zendaya’s sensational performance as Rue, a recovering drug-addict who slowly falls in love with the new trans girl that moves to her small town, is incomparable. Sure, Sandra Oh and Jodie Comer are just as good as ever in Killing Eve’s third season — but the show itself has overstayed its welcome. I’ve heard good things about Laura Linney, too, but, well, it’s Ozark... That leaves The Morning Show’s Jennifer Aniston. Next to Billy Crudup, Aniston, playing an established morning show host who slowly realizes how much power she doesn’t have when her male co-host is ousted following claims of sexual harassment, is the primary reason to watch this accidentally campy Apple TV+ show.

Outstanding Supporting Actor in a Drama Series

Who Will Win: Giancarlo Esposito, Better Call Saul

Who Should Win: Billy Crudup, The Morning Show

With three very different Succession actors going head-to-head, I find it hard to imagine that any single player comes out on top (though my money would be on Matthew Macfadyen if so). Similarly, I can’t imagine this award going to Jeffrey Wright, given the waning interest in Westworld, nor to The Handmaid’s Tale’s Bradley Whitford. This mostly leaves Giancarlo Esposito, whose performance I can’t vouch for given my lack of familiarity with Better Call Saul, but who I can trust given my affinity for Breaking Bad, The Mandalorian, and the currently-airing The Boys. If I had my druthers, however, the award would go to Billy Crudup, the main reason I tuned into The Morning Show every week last year. As the network’s new “big wig,” Crudup clearly delighted in his role as a pompous media executive with big ideas. Never has villainy looked so good.

Outstanding Supporting Actress in a Drama Series

Who Will Win: Sarah Snook, Succession

Who Should Win: Sarah Snook, Succession

Unlike the men in her show, Sarah Snook is at an advantage as the only Succession player in her category. Even if she is surrounded by some legitimate heavyweights, it’s rather easy to cross some names off — I don’t foresee Killing Eve’s Fiona Shaw, The Handmaid’s Tale’s Samira Wiley, or The Crown’s Helena Bonham Carter taking home the gold, no matter how good their performances are (Bonham Carter’s as Princess Margaret, in particular). I’d argue the same for Meryl Streep and Laura Dern, two industry legends that, unfortunately, are both up for Big Little Lies — a show that feels like a distant memory. That leaves Westworld’s Thandie Newton and Ozark’s Julia Garner, who have both won in this category before, in 2018 and 2019 respectively. While that would normally push me to believe that it’ll ultimately come down to a battle between them, I believe in Sarah Snook’s chances. As the sole female heir to the Roy dynasty, Shiv spent season two trying to prove herself worthy in a club largely deemed exclusive to men. It was a role doused in complicated, white feminist politics, and was incredibly acted, at that. Let’s get at least one acting award for Succession, please!

Outstanding Limited Series

Who Will Win: Watchmen

Who Should Win: Watchmen

In terms of sheer nominations, Watchmen washed its competition by a landslide. That’s reason enough to believe that the HBO sci-fi series has the support of the Television Academy. (Nevermind that it was one of 2019’s most critically-acclaimed shows.) Still, Watchmen stands against some tough competition — including the star-studded Phyllis Schlafly origin story Mrs. America and Netflix’s touching Hasidic narrative Unorthodox. Unbelievable, an incredibly powerful story about two women’s efforts to catch a rapist, is fantastic, too, though I imagine its September 2019 premiere is distant enough that voters won’t feel nearly as passionate about it. And with Reese Witherspoon missing out on an acting nomination for Little Fires Everywhere, it’s hard to believe that the series resonated with anyone in any lasting way. This is Watchmen’s to lose.

Outstanding Television Movie

Who Will Win: Bad Education

Who Should Win: Bad Education

Look at it this way. If HBO weren’t the ones to swoop in and buy Bad Education at last year’s Toronto International Film Festival, instantly relegating it to “Made-For-TV-Movie” purgatory, it probably would have been surefire Oscar bait. None of the other movies in this category can say that.

Outstanding Lead Actor in a Limited Series or Movie

Who Will Win: Hugh Jackman, Bad Education

Who Should Win: Hugh Jackman, Bad Education and Jeremy Pope, Hollywood

It is my humble opinion that this award should be two separate categories. Acting in a movie is much different than acting in a series. It’s why we have both the Oscars and the Emmys, goddamnit! That being said, Hugh Jackman is phenomenal in Bad Education — I agree with everyone that has praised his performance as a closeted school principal that lets his greed overtake his interest in actually helping his students. But I’m equally enamored by Jeremy Pope’s limber performance in Hollywood as a sex worker-cum-Oscar-winning screenwriter, which can only be described as a “breakout.” And before you all call me out, I did squeeze in a few episodes of Normal People as research, despite my earlier refusal to do so. The rumors are true — Paul Mescal is great in it! But my earlier arguments still stand.

Outstanding Lead Actress in a Limited Series or Movie

Who Will Win: Regina King, Watchmen

Who Should Win: Regina King, Watchmen

There was a time — just a few months ago, in fact — where I would have predicted Cate Blanchett walking to an easy win in this category. Playing real-life political figure Phyllis Schlafly in Mrs. America, Blanchett is uncannily effective as an uncaring, conservative homemaker that slowly realizes her power as the future leader of the STOP ERA movement. But in light of recent civil unrest, I think this category has become another Moonlight vs. La La Land, with Watchmen’s Regina King occupying the Moonlight spot. Though both performances are powerful, King plays a Black cop who comes to understand how intrinsically evil the system she works for is at its core while Blanchett plays a literal right-wing activist whose claim-to-fame is actively campaigning against the feminist movement. Shira Haas is astonishing in Unorthodox, while both Kerry Washington and Octavia Spencer do serviceable work in their respective streaming service vehicles. But in the end, it can only be Regina King. It has to be.

Outstanding Supporting Actor in a Limited Series or Movie

Who Will Win: Jim Parsons, Hollywood

Who Should Win: Jim Parsons, Hollywood

It took me a while to come to a conclusion about who I thought would win in this category. Of the six nominees, five have the unfortunate fate of being nominated against other people from the same show, with three Watchmen actors and two from Ryan Murphy’s Hollywood. But since I don’t see Unbreakable Kimmy Schmidt’s Tituss Burgess edging the others out, I went against my usual vote-split theory to put my support behind Jim Parsons, an actor Emmy voters clearly revere for his long-running stint with The Big Bang Theory but one I largely ignored until I met him as Hollywood’s real-life talent agent Henry Willson, a lascivious closeted gay man who routinely took advantage of the predominantly hunky men he counted as his clientele. It’s often hard to make characters as despicable as Henry feel likeable, and yet, whenever Parsons wasn’t on camera, I was dying for him to come back. That’s power.

Outstanding Supporting Actress in a Limited Series or Movie

Who Will Win: Jean Smart, Watchmen

Who Should Win: Toni Collette, Unbelievable

Yet another category that is completely swamped by one show. Here, it’s Mrs. America, which nabbed nominations for stars Uzo Aduba, Margo Martindale, and Tracey Ullman, all playing real people. (How, exactly, previous Emmy winner Sarah Paulson failed to make the cut is beyond me.) Naturally, I don’t imagine any of these players edging the other out, and as great as Holland Taylor is, I don’t think her contributions to Hollywood were grand enough to secure her a win. That leaves us only two other contenders — industry legend Jean Smart, whose whip-smart take on Watchmen’s Laurie Blake was hard to ignore, and fellow industry legend Toni Collette, who imbued her Detective Grace Rasmussen with a much needed dose of palpable sensitivity. With the widespread support for Watchmen, I anticipate Jean Smart taking it home. But if I had a choice, I’d give it to Toni Collette, whose performance was a large reason this inherently dark story often felt light, uplifting, and most of all, inspiring.