Dolan and Weinstein were friends for many years and in 2014 Weinsten was hired to work on Radio City Music Hall "Spring Spectacular” featuring the Rockettes -- an October 2017 article in the New York Daily News said the famous dancers were “relieved” to be rid of the “creepy" former Miramax executive. Dolan was part of the Weinstein Company board from mid-2015 to June 2016 and was named as a co-defendent with Weinstein in a lawsuit filed in December by six women who said they were assaulted and/or harassed by Weinstein. As a board member, Dolan allegedly knew of Weinstein’s “pattern and practice of predatory sexual conduct toward women” according to the lawsuit.
A source close to Dolan tells us the song is Dolan’s way of dealing with guilt over Weinstein with lyrics like "I should’ve thrown myself across the his tracks, stopped him from these vile attacks,” the song’s hook says. "We believed and didn’t see, through the lies he told us all, that led him to his endless fall, I should’ve known."
The song “I Should’ve Known” features layers of harmonies with Dolan and guitarist Marc Copely singing in tandem, and violinist Erin Slaver and guitarist Carolyn Dawn Johnson singing together on backing vocals. The self-reflective folk song was influenced by Simon & Garfunkel’s iconic folk-rock hit “The Boxer” and Dolan has said in the past that he is inspired by Fleetwood Mac, Crosby, Stills, Nash & Young, The Civil Wars, Jefferson Airplane and others.
The song drops as the Americana band prepares for the release of The Great Divide, due out in October. The album is being recorded at Sound Stage Studios in Nashville with producer Marc Copely, who produced the band’s 2017 album, Good Night, And Good Luck.