Suggestions by @tajimaru

Laurence Fishburne

as John Africa in MOVE

Ving Rhames

as John Africa in MOVE

Danai Gurira

as Martine Moïse in Assassination

Geena Davis

as Helen La Lime in Assassination

Lance Reddick

as Jovenel Moïse in Assassination

Antonio Banderas

as Whiskey in Assassination

Benicio del Toro

as Whiskey in Assassination

Jimmy Jean-Louis

as Léon Charles in Assassination

Austin Butler

as Frank Harris in Cool World

Kevin Clash

as Puppeteer in Happytime

James Gunn

as Director in Happytime

Brian Henson

as Producer in Happytime

Kevin Clash

as Choreographer in Happytime

Issa Rae

as Mac in Earth Girls are Easy (gender swapped)

Lizzo

as Zephyr in Valiant Cinematic Universe

Lizzo

as Faith Herbert in Faith

Samuel L. Jackson

as Raspberry in Darktown Strutters

Rob Riggle

as Cross in Darktown Strutters

Regé-Jean Page

as John Prince in Scarlet Street

Alexandra Shipp

as Kitty March in Scarlet Street