This time around it's a much bigger sound from a much bigger band, which Holland says led to a major breakthrough that enabled her to make the record she always wanted to make.
"I realised I'd been trying to do something like this for a long time. This was how I intended a lot of the material to sound, but I just couldn't get the musicians to do what I wanted them to do. Even Indigo Street -- she's a very prominent guitarist on the record and we'd been playing together for a long time -- didn't understand what I wanted her to do -- until I got a giant band.
"There are two drummers on every single song, and that kind of put everyone on edge, to stand and deliver what I needed."
Holland spent a good deal of time trawling New York's experimental scene for the perfect band, adding to the mix a raft of esteemed musicians, including Doug Wieselman, who has worked with Lou Reed, and Antony and the Johnsons.
"He's kind of a magic player. He's just a super beautiful musician," Holland says.
The end result is a self-produced rough and raw, sometimes uncomfortably discordant, other times groggy, even eerily quiet, mash of music that only a gutsy artist such as Holland could pull off.
It's unconventional to say the least, but Holland insists it's never been about sticking a finger up at the mainstream. It's just about doing what feels right.
"The thing is I'm not really saying 'f*** you all'. What I'm doing is making art. I'm really not trying to be combative, I just want to make music, that's really all."
Jolie Holland's album Wine Dark Sea is out now.