Drummer and guitarist Adam Dutkiewicz recalled the song's genesis to Metal Hammer: "We all used to just jam in a basement, and I was in there on my own and came up with some drum patterns, then I added some riffs to it." "By the time the rest of the guys turned up for practice I felt like I had something new to show them, so we just toyed with it! Joel [Stroetzel, guitar] came up with the riff that comes in at the end, but we collectively flushed it out together pretty quickly."
Vocalist Jesse Leach explained the song's lyrical content: "'My Last Serenade' has a lot of meanings for me. It's really about burning bridges. There comes a time when you have to leave people behind and just let them know that you care and there's only so much love you can give somebody until they drag you down with them."
This became Killswitch Engage's breakthrough song after its video gained heavy rotation on MTV's Headbanger's Ball.
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