What are some memorable roleplay exercises you've done before?

[Evergreen01]

Now, the title may sound a bit strange- But I have a couple minutes on here before I go to sleep and this came to mind.

Assuming you've held long careers in various forms of roleplay, you've likely experimented a little with different ideas; or even tested yourself with particularly challenging roles! This topic aims to look at the latter of those two. I refer to these things as "exercises," as they help you to work out and broaden your skill as a roleplayer, regardless of the specific roleplaying field.

For my example: I once played for a oneshot of highly-homebrewed D&D 5e as a four-headed gnoll, multiclassing into four classes (paladin, cleric, fighter, and barbarian; tied to each head). The character called himself R.Y.A.N., which was formed from the first initials of all four heads' names. The challenging part about playing this character was differentiating each head's personality and voice from one another, without slipping on character accents (it was a voice call) and with keeping in mind which head was tied to which class.

Reginald was the boastful, arrogant and posh Paladin, who viewed all the other adventurers as bumbling idiots and amateurs.

Yusef was a quiet, psychopathic Fighter. He wanted to see his enemies beg for mercy as their bones would crunch under his foot. Also he had a Swedish accent.

Andrew was the level-headed, calm Cleric, much more passive than the others and with a bit of a more moral side.

Nicolai was an honor-bound, thrill-seeking Barbarian with a thick russian accent, who lived for combat and pain.

Overall, it was probably the most difficult, yet engaging experience I've had roleplaying in D&D. Now, enough about me- I'd like to know what challenges you all have set for yourselves in the past-!

[Gangsta Moll Deactivated]

I have almost always so far played versions of my real self: but I very much enjoyed, recently, playing someone much more ready to take charge of a sexual situation and both exploit and to some extent control the man. It was challenging because very different from myself, but incredibly erotic and sexually arousing.

[bumpnrun]

Nothing like stepping out and trying something new...awesome!