What? On her heart-wrenching 2006 record, Over the Mountain, Across the Valley and Back to the Stars, Jennifer O'Connor treads lightly in Elliott Smith territory, mourning the deaths of her two sisters (one from brain cancer, another in a car accident) with acoustic guitar in hand, letting melody soar above sadness.

Nearly every weekend, as SPIN.com traverses the U.S. to cover the many festivals this summer, we cross paths with a number of the most politically-minded names in music, giving each a chance to smile for the camera and sound off on the 2008 presidential election.

What? The occasionally off-kilter underground project the Music Tapes is the brainchild of Julian Koster, most notably of seminal indie rockers Neutral Milk Hotel. Koster's third Tapes LP, Music Tapes For Clouds and Tornadoes, out now on Merge, guides listeners on a magical mystery tour of sorts.

Who? Hopeful Monster head Jason Ball began his studio experimentations in rural Nova Scotia, Canada before settling comfortably amidst the Toronto indie scene where he crafts '60s piano-pop throwbacks, building staccato, Zombies-style ditties and updating each with electronic flourishes.

What? It was all Discmans, FM radio, and the tail-end of the flannel era when Toadies frontman Vaden Todd Lewis offered to take us "behind the boathouse" to show his "dark secret" on the band's 1994 crossover hit "Possum Kingdom."