16 Most Shocking Emmy Wins of the Last 16 Years, From the ‘Schitt’s Creek’ Sweep to Katherine Heigl’s ‘Grey’s Anatomy’ Upset

Kerry Washington has delivered two supporting actor drama shockers in her lifetime. The most recent was calling Tobias Menzies (“The Crown”) over the late Michael K. Williams (“Lovecraft Country”). The other was in 2013, when many expected Jonathan Banks to finally get his due as Mike Ehrmantraut on “Breaking Bad” after submitting the episode “Say My Name,” which marks his final appearance on the show. Instead, after being a somewhat establishment nominee (and one-time winner) for guest actor comedy, Bobby Cannavale picked up his first main acting category win for playing Gyp Rosetti in the third season of “Boardwalk Empire.”

Michael Emerson’s work in ABC’s “Lost” is beloved, and his inclusion in this category is in no way saying he’s a “bad winner.” Instead, he won at the wrong time in the series. After losing to his co-star Terry O’Quinn in 2007 and shockingly losing to Željko Ivanek (“Damages”) in 2008, the ship seemed to have sailed for Ben Linus’ golden moment. Well, the Emmy voters didn’t think so when they checked his name off over Aaron Paul’s Jesse Pinkman for the second season of “Breaking Bad” and John Slattery’s Roger Sterling for the second season of “Mad Men.”

HBO’s “The Newsroom” had divided many critics and audiences, but the industry’s respect for its star Jeff Daniels was palpable. Many were excited the veteran actor had finally received his first career Emmy nomination for playing Will McAvoy. Still, many wrote it off as a career recognition, especially when going up against Bryan Cranston’s “Say My Name” episode of “Breaking Bad” and Damien Lewis’ “Q&A” episode of “Homeland.” Even Kevin Spacey’s role as Frank Underwood was considered a spoiler for the first episode of “House of Cards.”

The Emmys did not waste the opportunity, giving him his first career win, which had Daniels mentioning the last time he received an award was from the AARP Awards.

The final season of “The Sopranos” was an event for the ages. The HBO crime drama’s sixth season was a slam-dunk choice for outstanding drama series in 2007, with pundits expecting many of its actors to receive repeated love or first-time coronations. Instead, despite winning drama series, none of the actors won for their final seasons, most notably James Gandolfini as the iconic Tony Soprano. Instead, Gandolfini lost out to James Spader’s Alan Shore, who picked up his third win for NBC’s “Boston Legal.”

A recent shocker, along with “The Crown” sweeping the drama categories for Netflix, came within the show’s own ranks on Emmy night. It was presumed that Emma Corrin’s lauded portrayal of Princess Diana would prevail in lead actress drama after wins from Critics Choice and Golden Globes. In the end, her co-star Olivia Colman as Queen Elizabeth I, who had lost the year prior to Zendaya (“Euphoria”), beat her out.

When Tatiana Maslany received her second consecutive Emmy nom for the BBC America series “Orphan Black,” fans of the show were delighted she was being named next to former winner Claire Danes (“Homeland”). The 2016 race for lead actress drama had shaped up to be another showdown between the category’s previous year’s winner Viola Davis (“How to Get Away with Murder”) and Queen Bee Cookie Lyon, played by Taraji P. Henson (“Empire”).

Maslany split the difference, becoming the first lead actress drama recipient to win the sole nomination for her television show since Patricia Arquette for “Medium” in 2005.

Watching Steve Carell walk away from “The Office” was sad, especially since the show would continue without him. However, after years of watching Carell lose multiple times to Tony Shalhoub (“Monk”), Alec Baldwin (“30 Rock”), Jim Parsons (“The Big Bang Theory”) and most egregious, Ricky Gervais (“Extras”), no one thought the Emmys would let one of the most iconic characters in TV comedy history leave us without proper recognition.

Well, he did. Carell’s episode submission of “Goodbye, Michael” did not affect voters, who instead gave a second consecutive statue to Sheldon Cooper (Parsons) for the fourth season of “The Big Bang Theory.”

It’s a travesty.

Sandra Oh was on fire in 2009. After hosting the Golden Globes with Andy Samberg, she was nominated for lead actress drama for the second time for the BBC America series “Killing Eve,” along with drama series as an executive producer. With high-profile wins from Globes, Critics Choice and SAG, she nearly swept the TV awards season.

And without warning, presenter Gwyneth Paltrow said her co-star Jodie Comer’s name as the winner of the category, sending shockwaves throughout the industry. It’s gone down as one of the most jaw-dropping switcharoos ever.

In 2006, “My Name is Earl,” starring Jason Lee, was a critical and ratings hit for NBC. However, like many high-concept comedies, the TV Academy didn’t seem to “get it” for its first season. As a result, the show was only nominated for five Emmys — directing (Marc Buckland), writing (Greg Garcia), editing, casting and supporting actress comedy (Jamie Pressly), missing the big categories like lead actor comedy (Lee) and outstanding comedy series.

TV Academy voters must have felt bad about it because it took home four statuettes, except Pressly (who lost to Megan Mullally for the final season of “Will & Grace”). The “Pilot” episode joined a select group of episodes to win both writing and directing for the same episode. It also became the first show to win both categories without being nominated for a comedy series.

ABC’s “Modern Family” became an Emmy darling, winning four consecutive prizes for outstanding comedy series (all of which were warranted). At the time, it was tied with “All in the Family” and “Cheers” as the second most-winning show.

When it came to the show’s fifth season, it was going up against the first seasons of Netflix’s “Orange Is the New Black” and HBO’s “Silicon Valley” along with the third season of HBO’s “Veep” and the fourth season of “Louie.” Even CBS’ “The Big Bang Theory,” which had wrapped its seventh season, was bringing the narrative that it was time to reward the most-watched show on television (at the time).

But many critics also felt that the quality of “Modern” was trending downward. On Emmy night, Ty Burrell upset Tony Hale (“Veep”) and the show was able to squeak out a win for directing (Gail Mancuso) against Jodie Foster’s “Lesbian Request Denied” episode of “Orange.” With it losing all of its other categories, including Creative Arts, it looked like its run was ending. But the TV Academy decided to tack one more on for its troubles, giving it a fifth win and tying with “Frasier” as the most-awarded comedy series of all time.

Charlie Sheen went on a tirade when he declared himself “winning” before being fired from “Two and a Half Men.” When he left, it was up to the once Emmy-awarded (in supporting actor comedy) Jon Cryer to take up the mantle as the show’s new leading man. With Jim Parsons (“The Big Bang Theory”) and Alec Baldwin (“30 Rock”) on a roll, everyone assumed one of those two would be walking away with the statuette once again. Ultimately, the TV Academy opted to go with Cryer’s newly appreciated role as Alan Harper.

The 59th Primetime Emmy Awards produced some of the biggest surprises in Emmy history. From winners such as Sally Field (“Brothers & Sisters”) and Jaime Pressly (“My Name is Earl”), the ceremony had it all. However, one year after “The Office” won for outstanding comedy series but failed to award Steve Carell’s turn as Michael Scott; it seemed pre-ordained that he would walk away with his first acting statuette for the show’s third season that included classic episodes such as “A Benihana Christmas,” “Branch Closing” and the eventual writing winner “Gay Witch Hunt.”

Unfortunately, it wasn’t enough as the TV Academy opted for Ricky Gervais’ “Extras,” which he wasn’t there to accept. However, the sad moment offered a funny bit where Carell took Gervais’ Emmy and returned it to him at the next Emmy ceremony.

It’s not often that the Emmys reward a performer multiple seasons into a show’s run. Merritt Wever stans had rejoiced at the talented actress finally receiving her first Emmy nomination for playing Zoey Barkow in Showtime’s “Nurse Jackie.” With Julie Bowen winning for two consecutive years and her co-star Sofia Vergara yet to win, Wever seemed to be one of those “just happy to be here” noms. That is until the comedic duo of Tina Fey and Amy Poehler presented her first statuette in 2013. Nearly speechless, a tearful Wever could only say “thank you so much” twice before telling the room, “I gotta go, bye.”

It was 2011 when “Mad Men” won the outstanding drama series category for a fourth time, with pundits and audiences anxiously waiting to see the overdue moment of Jon Hamm’s Don Draper standing on the stage with a statuette in hand. After submitting the episode “The Suitcase,” considered one of the greatest episodes of the series ever, it seemed like a foregone conclusion. That’s until Kyle Chandler submitted the series finale episode “Always” of the high school football drama “Friday Night Lights.” In a jaw-dropping moment announced by the cast of the short-lived “Charlie’s Angels” reboot, the women screamed “Kyle Chandler!” Many of us did at home as well.

Considering Hamm finally got his due for his final season — no harm, no foul.

The first Emmys during COVID-19 may not have lit up the television ratings, but it remains one of the most significant ceremonies. This is primarily due to Pop TV’s “Schitt’s Creek” winning all seven comedy categories, including comedy series, becoming the first series to sweep every category. Pundits knew this outcome was possible, but were unsure that first-time nominee Annie Murphy had what it takes to win her category over former winners Alex Borstein (“The Marvelous Mrs. Maisel”) and Kate McKinnon (“Saturday Night Live”). But she did just that.

The Shonda Rhimes-created medical drama has had an undeniable legacy at ABC since premiering in March 2005. With 18 seasons and over 400 episodes, various favorite characters and actors have graced the screens, including Sandra Oh as Cristina Yang and Chandra Wilson as Miranda Bailey. However, one of the most shocking facts is Katherine Heigl remains the only main cast member ever to have won an Emmy for acting when she triumphed in 2007. The “it girl” of the time with the movie “Knocked Up,” she bested her two co-stars, Oh and Wilson, along with Lorraine Bracco and Aida Turturro in the final season of HBO’s “The Sopranos.”