Winstanley says Complicated Man stood out from the 12 tracks on their O'Brien-produced album How Red Is the Blood as the obvious song to enter for the Silver Scroll from the in the Scrolls.
"It's got the strongest narrative of all of our songs. That's a big thing for me in songwriting - writing a song, which has a strong narrative structure and one which points in one direction. For me, it's the best one on our album."
It's not surprising then that Winstanley counts songs from storytellers like Randy Newman as some of the best ever written. "Texas Girl At The Funeral Of Her Father has the perfect pairing of lyric and harmony and melody," he says.
He's also a big fan of the Glen Campbell classic By The Time I Get To Phoenix.
"So much said with so few, perfectly placed lyrics. Beautiful chords, too."
Kiwi legend, and two-time Silver Scroll winner, Don McGlashan gets a mention as well. "I love Anchor Me. It's such a beautiful song - that's another song that has a perfect pairing of lyrics and melody."
And so Winstanley knows Tattletale Saints have got their work cut out, following not only in the footsteps of the likes of McGlashan, but also up against tough competition this year, especially with teen powerhouse Lorde in the mix.
"It's like I'm a small shoe manufacturer and I'm going up against Nike or something, this huge power that I really don't have much control over," he laughs.
Ultimately, he's just thrilled Complicated Man is receiving the dues it's worth.
"The good thing about the Silver Scroll is that it's based on the song itself. So I think if all is fair, then we should be in good steps. I'm just stoked to be there."
The Silver Scroll will be awarded at Vector Arena, Auckland, on October 15.