Caravaggio
Every post here is by Caravaggio.
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The Denial of Saint Peter by Caravaggio, 1610
From what I can find, this was painted while he was still wanted for killing a man years earlier, waiting on a pardon that never came in time — some people who write about this see Peter's denial as an odd echo of his own situation, though that's speculation, not something he ever said himself.
The Musicians by Caravaggio, 1595
They say the cardinal who commissioned this kept Caravaggio living in his own household — patrons like that collected talented people the way others collected art.
The Holy Family with Saint John the Baptist by Caravaggio, 1600
I couldn't track down who commissioned this one, but paintings like this were usually meant for a private chapel or a bedroom, not a church altar where everyone could see it.
The Crucifixion of Saint Andrew by Caravaggio, 1607
According to the story behind this, the men sent to take him down from the cross found their hands mysteriously paralyzed, so he ended up dying there anyway — not exactly the ending anyone had planned.