1. Daniel Johnston
American singer, songwriter, musician, artist, and the subject of 2006's documentary "The Devil and Daniel Johnston." He's bipolar and despite being 47 years old, his songs come off very child-like. Here's an interesting story:
During a tour with Sonic Youth, Daniel was arrested for scrawling the Jesus Fish across the inside of The Statue of Liberty. As he finished painting the inside, Daniel was seen wandering the streets of New York City. Eventually, after spending hours driving around the city, he was located by the members of Sonic Youth. On a bus ride home from that same trip, he observed cow skulls littering the desert of Texas and came under the impression that the state was under the control of Satan. After getting off at the wrong stop, Daniel wandered around a foreign city all night. After entering the home of an elderly woman he believed was possessed by demons, the woman jumped from her second-story window in fright and broke both of her ankles. Other manic behavior Johnston displayed includes hitting his manager in the head with a lead pipe, and forcing his brother, Dick, under a shower, under the impression that the water would rid his 'demons'
At any rate, my favorite song of his is "True Love Will Find You In The End" from his "1990" album.
http://www.youtube.com/v/5ucN4DActxA
2. Yael Naim
French-Israeli singer/songwriter who became famous after her 2008 single "New Soul" was used in a commercial for the MacBook Air. This success made her the first Israeli solo artist to have a top ten hit in the US. She covered Britney Spears "Toxic" in 2007, and though I haven't listened to it, I'm sure she made it better. Here is "New Soul" off her self-titled album.
http://www.youtube.com/v/2gtbzS0PcEg
3. Kerli
Kerli is an Estonian pop musician that won a televised singing competition there. She has a contract with Island Def Jam and her debut album "Love Is Dead" is set to release on July 29. Her recent single is called "Walking on Air" (the video quality isn't that great, but it was the only one that allowed embedding.)
http://www.youtube.com/v/ErgicH5zL00
4. Sparklehorse
An American Rock group who I'd never heard of until about a year ago, despite their 1995 album "Vivadixiesubmarinetransmissionplot" which was a bit of a college radio hit and then their tour with Radiohead the following year. The band has collaborated with a lot of musicians like Tom Waits, PJ Harvey, and DJ Danger Mouse in their more recent albums "It's A Wonderful Life" (2001) and "Dreamt for Lightyears In The Belly of a Mountain" (2006) Off "It's A Wonderful Life" this is "Pianofire" (This is not the actual video, but it's the best sound quality I could find.)
http://www.youtube.com/v/vlksiuUJV1k
5. Skip James
I'm not just into up-and-coming and obscure indie groups. I've been having a real fascination with blues lately. I highly recommend the "Ghost World" soundtrack if you're interested. One of the songs featured is "Devil Got My Woman" by Skip James. It's a different version than the one in this video, but the fact that this kind of intimate footage of Skip James was even on Youtube was surprising in and of itself. Here's "Devil Got My Woman"
http://www.youtube.com/v/nYk4MTSq6uA