645 voters

Arguably the Worst Emmy Winners of All Time, Ranked

Updated June 19, 2019 1.8k votes 645 voters 13.5k views14 items

For each astounding, inspiring Emmy-winning actor that makes us laugh, cry, and feel real, human emotions watching their performances, there are an equal number of Emmy-winners who definitely don't deserve the honor. Some of these Emmy-winning actors were given bad roles, while others were just not as great as other nominees. Whatever the case, we've put together a list of the worst Emmy winners that really don't deserve the award they received for their work.

Louis C.K. probably wasn't happy after losing to Jon Cryer in 2012, but that kind of choice reveals a lot about Emmy voters. When an out-of-the-blue nominee wins an Emmy, certain questions tend to arise, such as: Do Emmy voters have cable? Are they giving their ballots to non-humans? Why William Shatner, and why now? The worst Emmy winners betray viewers' trust, and let down die-hard fans of other performances.

Some of these Emmy wins feel completely out of place. Kiefer Sutherland over Martin Sheen? Behind the Candlelabra over Top of the Lake? Are these worst Emmy winners a result of industry insiders thinking that they know best?

Not agreeing with an Emmy nomination or win doesn’t make the actor or show in question automatically bad. Many times, the worst Emmy wins are simply tone deaf in the context of the year and competition. Or they seem out of step in retrospect.

Vote up the worst Emmy Award winnings below.

  • The Win: Mad About You, Outstanding Lead Actress in a Comedy Series 1996 - 1999
    Who Didn’t Win: 1996 - Ellen DeGeneres (Ellen), Fran Drescher (The Nanny), Patricia Richardson (Home Improvement), Cybill Shepherd (Cybill)
    1997 - Ellen DeGeneres (Ellen), Fran Drescher (The Nanny), Patricia Richardson (Home Improvement), Cybill Shepherd (Cybill)
    1998 - Kirstie Alley (Veronica’s Closet), Jenna Elfman (Dharma & Greg), Ellen DeGeneres (Ellen), Calista Flockhart (Ally McBeal), and Patricia Richardson (Home Improvement)
    1999 - Jenna Elfman (Dharma & Greg), Calista Flockhart (Ally McBeal), Patricia Heaton (Everybody Loves Raymond), and Sarah Jessica Parker (Sex and the City)

    In a rather bizarre shut-out streak, Helen Hunt managed to thwart Ellen DeGeneres for three years in a row. Mad About You was an entertaining show, but the material, and Hunt, were not enough to grab four Emmys in a row. Ellen was groundbreaking and many thought DeGeneres deserved a nod at least two of those years.
    Questionable winner?

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  • The Win: Two and a Half Men, Outstanding Lead Actor in a Comedy Series, 2012 .
    Who Didn’t Win: Don Cheadle (House of Lies), Louis C.K. (Louie), Larry David (Curb Your Enthusiasm), and Jim Parsons (Big Bang Theory)

    Jon Cryer is probably best known and beloved for playing the role of Duckie in Pretty in Pink. But when his win shut out Louis C.K., Larry David, and Alex Baldwin, it was a total crying shame. Many felt that the award was given to Cryer out of sympathy for having to work with Charlie Sheen all those years.
    Questionable winner?

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  • The Win: 24, Outstanding Lead Actor in a Drama Series, 2006
    Who Didn’t Win: Peter Krause (Six Feet Under), Denis Leary (Rescue Me), Christopher Meloni (Law & Order: Special Victims Unit), and Martin Sheen (The West Wing)

    24 is great, but we're still not over the fact that Christopher Meloni won Best Butt in Primetime instead of an Emmy for his portrayal of Detective Elliot Stabler on Law & Order: SVU. Kiefer Sutherland's role on that show was simply not up to par with any of the above listed characters and actors.
    Questionable winner?

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  • The Win: Grey's Anatomy, Outstanding Supporting Actress in a Drama Series, 2007.
    Who Didn’t Win: Lorraine Bracco (The Sopranos), Rachel Griffiths (Brothers & Sisters), Sandra Oh (Grey’s Anatomy), Aida Turturro (The Sopranos), and Chandra Wilson (Grey’s Anatomy

    If Shonda Rhimes had a time machine, you can bet your britches that Katherine Heigl would not have an Emmy on her mantel for this particular role. Heigl power-tripped herself out of a career after bad mouthing Grey’s Anatomy and acting like a total diva on set. Although she made Denny's death on the show feel real to all who watched it, her later attitude towards her co-stars in general made us wish the award had been given to someone else.
    Questionable winner?