The 11 most horrible Emmy Award winners of all time

worst emmy winners ever

The Emmy Awards are upon us once again, that time of the year when everyone in the TV industry gathers to kiss each other’s asses and pretend that CBS produces quality shows. But while they’re busy doing that, we thought it would be a nice change of pace to take a moment and celebrate all those times when they kissed the wrong ass.

Yes, believe it or not, sometimes the infallible folks of Hollywood get it wrong. Way wrong. Okay, they usually get it some degree of wrong, but these are the times when they were really, really wrong, okay? So wrong, in fact, that the following are none other than the 11 worst Emmy Award winners ever.

11. Alex Rocco – Best Supporting Actor in a Comedy Series, 1990

Look, I have nothing against Alex Rocco. He always classes things up, and he was Moe Greene in The Godfather so no one should begrudge him his success. But that’s just it, Alex Rocco won his Emmy in 1990 even though he was pretty much the exact opposite of a success. After all, successful performances do not end up with the show canceled before it’s even lasted one season. And especially when that show is called The Famous Teddy Z. Remember that show? No? Anyone? Yeah. Making it even more inexplicable is it’s not like Rocco was up against a weak field. That was the heyday of Cheers, and there are at least four dudes right off the top of my head from that show alone that probably deserved it. Good for you, Moe Greene, but… no.

10. Jon Cryer – Best Actor in a Comedy Series, 2012

It was bad enough when Cryer won for Best Supporting Actor a few years earlier, but what in the hell is this nonsense? Look, no one should be giving an award for anything to Two and a Half Men, but this is even worse than that – this is Two and a Half Men AS (After Sheen.) I guess maybe people felt bad for Cryer for having to deal with Charlie’s shenanigans before getting stuck with the weird little brat who played his kid and Ashton Kutcher of all people. Give him a Purple Heart. I’d be okay with that. The man has been through a lot. But not an acting award. Are you really telling me he was better than fellow nominees Louis CK, Alec Baldwin, or Larry David? Is that the world we live in? This is just depressing.

9. Melissa McCarthy – Best Actress in a Comedy Series, 2011

Nope. Just… nope. Look, this is not about Melissa McCarthy. This is about her show, Mike & Molly, which I’m pretty sure is shown to new arrivals in hell. This seems like a case of two things – one, it was kind of a weak year for nominees, which two, made it easy for them to just give it to McCarthy since she was a rising star and everybody loves her for being Lady Farley. But do you know anyone – anyone at all – who loves Mike & Molly? I get that it gets good ratings, but are we sure there are actual human beings watching this? Are they showing it to prisoners and counting them in the numbers? Did they vote for this? I don’t get it.

8. Ray Romano – Best Actor in a Comedy Series, 2002

Ray Romano winning best “actor” for playing himself is a hell of a trick. But Ray Romano winning is really just the tip of the iceberg here because no show in history has been inexplicably rewarded and showered with awards show praise more than Everybody Loves Raymond. And I’m going to include every award the show ever won here, because if I complained about them all separately, it would make up the entire list. You have Ray winning for just showing up to work, but you’ve also got Patricia Heaton and Doris Roberts winning multiple times for playing maybe the two worst women in history, just complete and utter sitcom clichés of the sort of overbearing wives and mothers that helped ruin sitcoms for good, and then the show itself, which won for best series not once but twice, beating out Arrested Development and Curb Your Enthusiasm along the way. I’m just saying, we can do better. We can do better.

7. ‘Cathy’ – Best Animated Program, 1987

Everybody rags on The Simpsons these days, but people forget what a dark time it was for animation on TV before that show saved everything, and nothing proves that more than this. You know Cathy, right? It’s that dumb newspaper comic strip that nobody reads or likes. Well, for some inexplicable reason, CBS (who else?) commissioned an animated version, and even more inexplicably it was judged to be the best animated show on TV in the whole world in 1987. Just think about how ridiculous that is. Homer, I will never speak ill of you again.

6. ‘The Teen Files (The Truth About Drinking)’ – Best Children’s Program, 1999

This was the sort of ridiculous, uncool special that they show in health class to scare kids away from drinking, and somehow, it managed to not only wind up on the Emmy radar, it won the damn thing. The special itself featured a who’s who of popular teenage icons like Tyra Banks (hmmm…), Evander Holyfield (uh…) and Leeza Gibbons (what the hell?) dropping knowledge and trying to scare kids straight. Look, I would have been all for this if it was 30 seconds long and featured them saying “Here’s the truth, drinking is fun and it helps make life seem less shitty for a few hours,” but I’m guessing that’s not the direction they went in.

5. ‘Donahue and Kids’ – Best Children’s Program, 1981

In case you don’t remember Phil Donahue, he was basically the OG of the daytime talk show game. He begat Oprah and Maury and Springer and everyone else. Now imagine Maury or Springer devoting a show to discussing life threatening illnesses with a bunch of impressionable children. Pretty terrifying, right? Well, that’s pretty much what this was, and because I guess the world was just more innocent back then and didn’t worry about weirdoes like Donahue warping young minds, they didn’t just let this happen, they gave Phil an Emmy for it. No wonder Generation X ended up so fucked up.

4. William Shatner – Best Supporting Actor in a Drama Series, 2005

This happened. And hey, I love the Shat just as much as anyone else, but come on… really? Sure, he was entertaining in that Shatner way of his on Boston Legal, but are you really telling me that he was the best supporting actor on all of TV? Before you defensively answer yes, remember that this was when Lost and 24 were both crushing it, and are you telling me that Shatner was better than every dude on either of those shows? I think what happened here is this – 2005 was that weird year when The Sopranos went on hiatus, which meant that things were wide open for the first time in years and everybody loves Shatner, so… why not? Still – and I know this makes me a total asshole for saying this – this never should have happened.

3. Katherine Heigl – Best Supporting Actress in a Drama Series, 2007

We did this America. We’re all responsible for letting it happen. Well, some of you are more responsible than others. You know who you are. Anyway, this was just terrible. Let’s not even try to pretend otherwise, okay? Let’s just agree to never speak of it again and move on.

2. ‘High School Musical’ – Best Children’s Program, 2006

Man, looking at these winners for Best Children’s Program over the years it’s no wonder we all grow up to be such broken, dysfunctional idiots and assholes. I just want you to think about this. Really think about it. We live in a world where High School Musical is an award winning movie. We’ve done some terrible things as a species, but this is the one that other worlds will judge us by when they finally decide to vaporize us one day.

1. ‘The 63rd Annual Academy Awards’ – Best Variety Show, 1991

63rd academy awards
Yes, a show designed to give awards to famous people gave an award to another show designed to give awards to famous people. Got that? I don’t blame you if your brain shut off somewhere in the middle there. This is the snake eating its own tail of pop culture, a level of epic circle-jerkery that would be almost impressive if it wasn’t so dumb. It is a singularity of idiocy that I’m surprised didn’t immediately create a black hole and swallow all of reality. Say what you will about everyone and everything else on this list, but at least those were given to legitimate (if horrible) artistic projects. This, though, this is almost a masterpiece of lunacy, and therefore I have no choice but to award the award for worst Emmy Award winner of them all to the 1991 Emmy Award won by the Academy Awards, and please, let’s never, ever say the word “award” again. Okay? Okay.

Emmy Award image by s_bukley/Shutterstock
Cathy image: YouTube
63rd Annual Academy Awards image: YouTube

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