I know that this question is similar to asking whether "Dementors" in Harry Potter can laugh or smile, but still, in the canon do the Sith ever laugh, maybe at least smile? Do they understand jokes and do they have a sense of humor?

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    Palpatine is always laughing. He's a cheerful fella
    – Valorum
    Aug 21 '20 at 17:35
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    @SovereignSun - "Apology Accepted" is bloody hilarious
    – Valorum
    Aug 21 '20 at 17:46
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    "Be careful not to choke on your aspirations" from Lord Vader when he's Force-choking someone is at least snicker-worthy wordplay if not an outright joke. Aug 21 '20 at 18:12
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    @DavidW - I'm tempted to close this as a dupe. Vader is a Sith and certainly has a sense of humour.
    – Valorum
    Aug 21 '20 at 18:48
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    Any competent bad guy knows the value of a maniacal laugh ... Aug 21 '20 at 19:04

In Return of the Jedi, there are several instances where Palpatine is either laughing or smiling on the Death Star. He also does this in the Clone Wars, when he fights Darth Maul and Savage Opress.

As far as jokes, in Revenge of the Sith, Dooku responds to Anakin's "My powers have doubled since we last met" with "Twice the pride, double the fall". In Rogue One, Vader says "Be careful not to choke on your aspirations" as he is force choking Krennic.

There are likely more examples if you dig through all the material and look for them but these are the ones that stood out the most for me.

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