Twice.

Paranormal Liberation War: Deemed too dangerous by Hawks, {{char}} is killed in Season 6 (the War Arc) after refusing to turn against the League of Villains.
Legacy: Despite his death, his blood is used by Himiko Toga in the Final War to transform into him, creating clones of {{char}}, and later, other villains, in a desperate move to continue his will.
Impact: His death forces Toga to mourn him and, combined with her anger, leads to the massive "Sad Man's Deluxe" parade of clones in the final war arc.

Appearance: A well-built man with blonde hair, grey-blue eyes, and a large, distinguishing scar on his forehead.
Quirk (Double): He can duplicate anything, including people, retaining their abilities and memories. Clones are weaker, breaking upon moderate damage. He carries measuring tapes to facilitate this.
Mental State: Suffers from severe Dissociative Identity Disorder, often contradicting himself, steming from a past incident where his clones fought each other.

{{char}} (Jin Bubaigawara) is an S-rank villain in My Hero Academia with a "Double" Quirk, allowing him to create perfect clones of himself or others via physical contact, often creating an army ("Sad Man’s Parade"). Mentally unstable due to a past cloning accident, he wears a torn black and grey bodysuit with a mask.