The Emmys are television’s most important award show, the small-screen equivalent to the Oscars. Thus, many are deeply invested in the races, especially for the lead categories. When an actor wins an Emmy, and others don’t believe they should have won, think someone else deserved it more, or the win came unexpectedly, it’s typically called an upset. These divisive victories have happened many times throughout the Emmys’ 75-year run, and they’re among the award shows’ most prevalent situations.
Every few years, certainly at least once every decade, someone wins, and viewers at home don’t necessarily agree with the decision. It’s not to say that they failed to deliver a good performance or that they were entirely unworthy, but rather that someone else might have been ignored. Throughout the last eight decades, many Lead Actor wins across the comedy, drama, and miniseries categories have sparked uproar or at least conversation. From back-to-back wins for Ted Lasso to a puzzling victory for Hatfields & McCoys, these are the worst Lead Actor Emmy wins of each decade.
8 1950s: Sid Caesar – Lead Actor in a Comedy Series
‘Caesar’s Hour’ (1954-1957)
This may just be a sign of the times themselves, but Sid Caesar’s win for Caesar’s Hour seemed out of place. While it was in the comedy category, Caesar’s Hour was a live sketch comedy show. Perhaps because, in recent years, there’s a specific category for sketch comedy, the fact that an actor who focused entirely on skits won has people of this generation finding it odd. It’s not unheard of; some SNL performers actually make it all the way to the nominations, but none actually win.
Chalk this one up to the times, and the win could probably also be attributed to just how strong
Caesar’s Hour
was overall.
Caesar won in 1957 for the NBC series for playing various characters in the admittedly hilarious show, but he was up against heavyweights like Jack Benny for The Jack Benny Program. Caesar’s Hour was one of the top-winning shows overall for the ninth annual festivities, nominated in all four major categories, and swept all four. That record was broken in 2004 by Angels in America and more recently in 2020 by the cast of Schitt’s Creek. Chalk this one up to the times, and the win could probably also be attributed to just how strong Caesar’s Hour was overall. It’s still less than ideal and a victory that stands like a sore thumb during the decade.
7 1960s: Carl Betz – Lead Actor in a Drama Series
‘Judd, for the Defense’ (1967-1969)
Winning in 1969 for his lead role in the legal drama Judd, for the Defense, fans were surprised that Carl Betz took home the award when he faced competition from actors like Raymond Burr in Ironside and Peter Graves and Martin Landau from Mission: Impossible. Judd, for the Defense was the equivalent of a typical legal procedural today, following the flamboyant attorney as he handled controversial cases for the time.
The series only lasted two seasons, and today lacks the same staying power as other series from the time, further putting Getz’s win into question. It’s not necessarily a bad performance or an unworthy win, but it is a forgettable and uninspired one, especially in hindsight. Betz continued to act through to his death in 1978 but mostly had small roles in single episodes of shows, making his win against those heavyweights all the more puzzling.
Judd, for the Defense is not available to stream or buy in the US and Canada.
6 1970s: Ron Leibman – Lead Actor in a Drama Series
‘Kaz’ (1978-1979)
Rob Leibman, best known today as the voice of Ron Cadillac on Archer, took home the statue in 1979 for his role in the courtroom dramaKaz, one of the lesser-known crime series from that decade. That’s because the show only lasted a single season of 23 episodes before getting canceled. Yet, despite not ever attracting a big audience, the series about a former convict who becomes a criminal defense attorney after being released from prison earned Leibman the prestigious award.
Ron Liebman took home the statue in 1979 for his role in the courtroom drama
Kaz
, one of the lesser-known crime series from that decade.
What fans find most baffling is that Leibman won for his role in this short-lived series over Edward Asner in Lou Grant, James Garner in The Rockford Files, and Jack Lugman in Quincy, M.E., all shows that are arguably much more memorable than Kaz. Like the show itself, Leibman is good, but nothing out of the ordinary, and pretty much every other actor in his category delivered a far worthier performance.
Kaz is not available to stream or buy in the US and Canada.
5 1980s: Richard Kiley – Lead Actor in a Drama Series
‘A Year in the Life’ (1987-1988)
Towards the end of the decade in 1988, Richard Kiley won for his role in A Year in the Life. The otherwise unremarkable show was a three-part miniseries created by the creator of St. Elsewhere, one of the best medical dramas of all time, which gave it instant attention. This notoriety helped the show turn into a one-hour drama that lasted for 22 more episodes and followed the Gardner family through their lives as they dealt with the unexpected death of matriarch Ruth (Eva Marie Saint).
Kiley, who played the father and grieving husband, delivered a great performance in an underwritten show. Still, actors like Corbin Bernsen from L.A. Law, Ron Perlman in Beauty and the Beast, and Edward Woodward in The Equalizer were outstanding and would’ve been far more inspired wins in this painfully conventional category. What’s more, A Year in the Life didn’t bring in the ratings expected and was not renewed, making Kiley’s win one of, if not the most wasted of the 1980s.
A Year in the Life is not available to stream or buy in the US and Canada.
4 1990s: Christopher Lloyd – Lead Actor in a Drama Series
‘Road to Avonlea’ (1990-1998)
Road to Avonlea was a sweet Canadian series that was fairly popular, running for seven seasons. But Christopher Lloyd wasn’t even among the main cast and won this award in 1992 for a singular appearance in the episode “Another Point of View” — other actors in the category were nominated for specific episodes as well, but they had much meatier roles.
Lloyd’s victory was part of a rule change that year that allowed both regular and guest actors to compete in the same category; logically, it only lasted one year. Still, it allowed Lloyd to take home the award for a role in a single episode when others like Scott Bakula in Quantum Leap, Michael Moriarty in Law & Order, and Rob Morrow in Northern Exposure didn’t really get a fair shake. Lloyd’s victory stands out as one of the Emmy’s most misguided choices as a result of a nonsensical rule change.
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3 2000s: Ray Romano
‘Everybody Loves Raymond’ (1996-2005)
There’s no denying that Everybody Loves Raymond is an iconic sitcom, arguably one of the best comedies of the 2000s. But Ray Romano was part of a larger ensemble cast, many of which often overshadowed him. His character was particularly one note, delivering one-liners and goofy laughs and smiles to lighten the mood (and frustrate his wife). Romano was great in the series, of course, but looking at the other nominees, his win in 2002 had some people scratching their heads.
Consider that he was up against Kelsey Grammer for Frasier, Matt LeBlanc and Matthew Perry for the best season of Friends, and Bernie Mac from The Bernie Mac Show. Looking back, any of those four actors were probably more deserving of the win that year. In fact, Roman would’ve been a worthier winner any other year he was nominated; ain’t that the way? It’s also worth noting that his co-stars Brad Garrett and Doris Roberts won that year as well, while Patricia Heaton lost out to Jennifer Aniston from Friends.
2 2010s: Kevin Costner
‘Hatfields & McCoys’ (2012)
Oscar-winner Kevin Costner is one of the most accomplished actors around and a major small screen force of late, thanks to Yellowstone. That said, his role in the 2012 miniseries Hatfields & McCoys really didn’t warrant a nomination, much less a win. In fact, the show seemingly came out of nowhere to compete with some major hits in its category.
The History Channel miniseries about the Hatfield-McCoy feud during the Civil War was the network’s first scripted drama and would likely never have been considered had it not been for Costner’s presence. Yet the show received a total of 16 Emmy nominations in 2012 and took everyone by surprise when Costner’s name was called. Who did he beat? Benedict Cumberbatch from Sherlock: A Scandal in Belgravia, Idris Elba from Luther, Woody Harrelson in Game Change, Clive Owen in Hemingway & Gellhorn, and his co-star, the late Bill Paxton. It’s safe to say that year was slim pickings on the miniseries front, and even then, Costner was the weaker choice.
1 2020s: Jason Sudeikis
Ted Lasso (2020-2023)
This might be a controversial choice, but it pertains specifically to Jason Sudeikis’ second win for the title character in this comedy-drama about an American football coach who travels to England to coach a struggling English football team. Ted Lasso started on a high, and no one expected anyone else to win but Sudeikis in 2021. It was well-earned recognition for him and many of his other co-stars who also won or were nominated that year.
However, it was odd to see Sudeikis win again at the 2022 ceremony, which was broadcast almost a year after the second season premiered; in fact, Sudeikis’ first win happened while the show was airing its second season. Considering his competition, including Donald Glover in Atlanta, Bill Hader in Barry, Nicholas Hoult in The Great, and Steve Martin and Martin Short in Only Murders in the Building, many believe the award should have gone to one of those latter two comedy icons.
