Least favorite - if it counts - goes to the users from the left who cosplayed as Trumpists in 2015-2016 because they found it hilarious, and did so pretty much until Election Day. It wasn't funny then, and with the exception of their apparent horror at Trump's surprise victory (which I may be misremembering), it also wasn't funny in retrospect.
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Lief was a big time ironic Trump supporter in 2016.
Aye, Lief is the one I had in mind the most. If memory serves right, he had the most elaborate of the performances as well, including the aggressive Trumpian tone.