2019 Emmy Predictions for Comedy: Matt Roush Gives His Series & Acting Picks

CATEGORY: Outstanding Comedy Series

Barry, HBO
Fleabag, Amazon Prime Video
The Good Place, NBC
The Marvelous Mrs. Maisel, Amazon Prime Video
Russian Doll, Netflix
Schitt's Creek, Pop
Veep, HBO

Typically, Veep would be a slam dunk, having won the last three times it was eligible. And while it was in top form for its last viciously funny season, the political comedy faces tougher-than-usual competition, including last year's delightful champ, The Marvelous Mrs. Maisel. And HBO upstart Barry has nearly twice as many nominations as Veep. Another potential spoiler: the very buzzy and hilariously heartfelt Fleabag, which swept this summer's Television Critics Association Awards. Its star/creator, Phoebe Waller-Bridge, couldn't be hotter. There's really no bad choice in this bunch, including the trippy Russian Doll and, finding Emmy love after five seasons (and an audience once it landed on Netflix), the cult comedy Schitt's Creek.

Most Likely to Win (keeping Emmy history in mind)

Veep will be hard to beat.

Should Win

Much as I love Mrs. Maisel and Barry, and will miss Veep, I'd give my blessing to Fleabag and its "hot priest."

CATEGORY: Outstanding Lead Actress in a Comedy Series

Christina Applegate, Dead to Me
Rachel Brosnahan, The Marvelous Mrs. Maisel
Julia Louis-Dreyfus, Veep
Natasha Lyonne, Russian Doll
Catherine O'Hara, Schitt's Creek
Phoebe Waller-Bridge, Fleabag

As Selina Meyer, Veep's Julia Louis-Dreyfus has never lost for this role of a lifetime, and it's nearly impossible to imagine her being denied a victory lap in her seventh and final bid. But there's stiff, and sensational, competition from Mrs. Maisel herself (Rachel Brosnahan, who won in 2018) and Fleabag's brilliant auteur, Phoebe Waller-Bridge. And don't count out Natasha Lyonne, who took a break from Orange Is the New Black to co-create and star in Russian Doll. As her seemingly immortal character of Nadia might quip: How many times does someone have to die to win an award around here?

Most Likely to Win

Julia Louis-Dreyfus (but don't be shocked if there's a Phoebe Waller-Bridge upset)

Should Win

Phoebe Waller-Bridge (though I'd settle for her winning a writing Emmy)

CATEGORY: Outstanding Lead Actor in a Comedy Series

Anthony Anderson, black-ish
Don Cheadle, Black Monday
Ted Danson, The Good Place
Michael Douglas, The Kominsky Method
Bill Hader, Barry
Eugene Levy, Schitt's Creek

Emmy voters have a habit of making former winners repeat winners, which means the smart money is on last year's champ, Bill Hader, to triumph again for his very successful second season of the dark hitman comedy. (Plus, he writes and directs!) But I'll go out on a limb to predict Michael Douglas will add a second Emmy (his first was as Liberace in Behind the Candelabra) to join his Oscar, for his wry performance as an acting coach past his prime in the wonderful The Kominsky Method — which deserved a Comedy Series nomination, by the way. Ted Danson is undeniably a legend, and a blast as the otherworldly Michael on The Good Place, so could be a sentimental favorite as well.

Most Likely to Win

Michael Douglas (unless a Barry sweep puts Bill Hader back on top)

Should Win

Michael Douglas

CATEGORY: Outstanding Supporting Actress in a Comedy Series

Alex Borstein, The Marvelous Mrs. Maisel
Anna Chlumsky, Veep
Sian Clifford, Fleabag
Olivia Colman, Fleabag
Betty Gilpin, GLOW
Sarah Goldberg, Barry
Marin Hinkle, The Marvelous Mrs. Maisel
Kate McKinnon, Saturday Night Live

This is tough. These are some funny and seriously talented ladies, and it's hard to bet against two-time winner Kate McKinnon for her rogue's gallery of SNL scene-stealers, although Mrs. Maisel's lovably gruff Alex Borstein won last year and could easily repeat for playing Midge's most loyal champion. Olivia Colman is on a roll after winning an Oscar — and we can't wait to see her as Queen Elizabeth in The Crown — but her venomous Godmother on Fleabag this year didn't make as big an impact as in the first season. Anna Chlumsky has long deserved a win (this is her sixth try) as Veep's put-upon flunky, and Betty Gilpin glows as a lady wrestler on GLOW. So no shortage of good choices.

Most Likely to Win

Alex Borstein (although a surge for Fleabag could propel Olivia Colman to her first Emmy win)

Should Win

Alex Borstein or Anna Chlumsky (for keeping a straight face all these years)

CATEGORY: Outstanding Supporting Actor in a Comedy Series

Alan Arkin, The Kominsky Method
Anthony Carrigan, Barry
Tony Hale, Veep
Stephen Root, Barry
Tony Shalhoub, The Marvelous Mrs. Maisel
Henry Winkler, Barry

Some Emmy favorites are vying for the prize in this tight category — Tony Hale won twice for playing Veep's obsequious Gary, and Tony Shalhoub took home three as Monk. And while the beloved Henry Winkler more than deserved his first-ever win last year as Barry's acting coach, and could ride a Barry tide, no one can beat Oscar winner Alan Arkin for comedic pathos as the newly widowed curmudgeonly super-agent on The Kominsky Method.

Most Likely to Win

Alan Arkin (with Henry Winkler a definite possibility to repeat)

Should Win

Alan Arkin, for making us cry as well as laugh