Duration: 1:24:06

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Not all main bosses are listed here. I just listed the bosses I felt I would even classify as difficult. Most of these fights were done in NG. The Nameless Puppet and the Walker of Illusions bonus cheese fight were done on NG+. I would say that bosses became about twice as hard in NG+. I struggled with just about all bosses without bringing in the NPC Specter backup. I would say this list may change a bit more if I didn't have the backup.
00:00:00 - Start
00:00:07 - 14. Parade Master/Corrupted Parade Master
00:01:57 - 13. Black Rabbit Brotherhood Part 1
00:06:35 - 12. Champion Victor
00:11:44 - 11. Robber Weasel
00:14:09 - 10. Simon Manus
00:24:47 - 9. Scrapped Watchman
00:26:43 - 8. Black Rabbit Brotherhood Part 2
00:31:21 - 7. Laxasia
00:44:26 - 6. Fallen Archbishop
00:49:29 - 5. Fuoco
00:52:10 - 4. King of Puppets
00:58:39 - 3. Walker of Illusions
01:01:01 - 2. Green Monster of the Swamp
01:12:29 - 1. Namless Puppet
01:22:13 - Bonus: Walker of Illusions Cheese Method