Halloween: The Curse Of Michael Myers revealed the identity and motives of the sinister Man in Black, but did he survive the events of the sequel? The Man in Black has his origins in Halloween 5: The Revenge Of Michael Myers. This 1989 sequel was rushed into production following the success of the previous entry, 1988's Halloween 4. The fifth entry was later lambasted for its bizarre story and odd stylistic choices - though its since attracted a cult for that very reason too. During production, the filmmakers added the Man in Black character both to tie some loose plot threads together and set up a sequel hook.
The mysterious Man in Black has a few scenes in Halloween 5 and bears the same tattoo mark as Michael. In the ending, he shoots up a police station to free the captured Michael. The filmmakers didn't know for sure who this figure was supposed to be, with some believing it was Michael's twin brother. The sequel received largely bad reviews and underperformed, so it was six years before fans received any kind of answer.
1995's Halloween: The Curse Of Michael Myers revealed the Man in Black was actually Dr. Terence Wynn (Mitch Ryan), the administrator of Smith's Grove in the original film. The sixth movie revealed he's part of the Cult of Thorn, who placed a curse on young Michael Myers with the Mark of Thorn. This Cult of Thorn curse drove Michael to kill his bloodline and gave him inhuman strength. In the theatrical cut of Halloween 6, Michael decides to break free of the cult's influence and massacres most of its members, with a horrified Dr. Wynn seen amongst the bloody chaos.
While some followers of the series debate whether he lived or died, it's worth noting Dr. Wynn isn't actually shown dying on screen in Halloween 6. It's entirely possible Michael did kill him along with the rest of the cult, but his death isn't depicted either. This likely means producers were keeping their options open for a potential seventh movie with the Man in Black returning. A sequel exploring the character and his origins was also considered for Halloween 9 before the franchise was rebooted with Rob Zombie's 2007 Halloween remake.
The Man in Black DOES die in the alternate Halloween 6 "Producer's Cut," however. This was the original version of the sequel before Dimension demanded sweeping reshoots to the third act to add more gore. The final scene of this version sees Dr. Loomis re-enter the clinic to look at Michael's body - only to discover it's Wynn in the mask and Michael has escaped dressed as the Man in Black. Wynn then passes the Thorn mark to Loomis, dying as he makes Loomis Michael's new guardian. This could have been an intriguing new angle for the series, but sadly, Donald Pleasance passed after filming his scenes and this ending was later scrapped.