I don't know where the term freak folk comes from but I really like it. It describes the kind of eclectic and experimental music that I find very fascinating.
Danielson (a.k.a. Danielson Famile)
Daniel Smith's quirky take on song writing and even quirkier voice is an acquired taste, but if it wasn't then it wouldn't be freak folk would it? While this large sibling band is not well known, its influence is strong. Among others, Danielson had a strong influence on a young, ambitious musician named Sufjan Stevens, who often played with the family before pursuing his own musical career. Ships is Danielson's weird masterpiece.
"Before our time, upon a noun there stood still a ship standing proud."
Neutral Milk Hotel
Neutral Milk Hotel released In an Aeroplane Over the Sea in 1998. It has since become a cult classic among indie and folk fans. Fusing raw acoustic passion, punk rock energy and abstract storytelling, Jeff Mangum crafts songs that are at once honest, catchy and lurid. It's quite an experience.
"I can't believe how strange it is to be anything at all."
mewithoutYou
In 2009 mewithoutYou wrote a collection of bizarre campfire songs/parables, many from the perspective of surprisingly pious and philosophical animals and vegetables. The album, named It's All Crazy! It's All False! It's All a Dream! It's Alright, is creative, humorous and profound, and would make Saint Francis of Assisi very proud. The influence of producer (and aforementioned) Daniel Smith is present, adding a playfulness not present in previous records. Three years later and it's still my favourite album of all time.
"The strawberry said to the tangerine
my face is red but our hats our green."
On a side note, if you look hard on youtube there are a few videos of Aaron Weiss (mewithoutYou) covering some Neutral Milk Hotel Songs. Talk about worlds colliding.