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Anytime a comedian takes on a dramatic role and nails it.
Off the top of my head….
Robin Williams: Dead Poets Society (and many more, I think that was his first) Bill Hader: Barry. Jim Carrey: Eternal Sunshine of the Spotless Mind
Don’t forget about Bryan Cranston either! He was that weird but hilarious dentist from Seinfeld and the dad in Malcolm in the Middle way before he ever was Walter White.
Man, Robin Williams can get to me like no one else. There were moments in Good Morning Vietnam, a couple years before Dead poets, but GMV was def more focused on his big comedic personality. Then his performance in The Fisher King...I don't generally get emotional about celebrities but that dude was different. There's been a few musicians that have been much better than expected. Dolly Paton in 9 to 5, Madonna on A League of their Own, Prince's acting in Purple rain. Ice Cube in Boyz in da hood.
Awakenings was another one, right after Dead Poets Society.
You often hear comedians are the best actors because they learn to act through humour which is is probably the most abrupt emotions to react to
I've heard it more that both comedy and drama is like a dance, but comedy has a faster tempo.
I figure it's also because they're on stage so much and trying to convey so much to an audience so often. There's gotta be a lot of transferrable skills.
I really loved Melissa McCarthy in Can You Ever Forgive Me? She nailed that one