Jonathan Wolf was born in Cincinnati, Ohio to Messianic Jewish parents. Before his first year in high school, Wolf discovered an old 4-track in his father's synagogue and began to experiment musically. His forays into rapping, drumming, and poetry followed.
In 1997, while attending art school at the University of Cincinnati, Wolf met fellow student Adam Drucker—better known as Doseone—at the semifinals of the 1997 Scribble Jam. Doseone and Wolf formed the live improvisational group Apogee, along with Yoni's brother Josiah and DJ Mr. Dibbs. The partnership of Wolf and Doseone continued for many years under many guises, including Greenthink and, most notably, cLOUDDEAD.
In 2005, WHY? released Elephant Eyelash, which deviated considerably from their previous full-length Oaklandazulasylum, primarily as less of an independent solo project to more of the sound of a full indie rock band. To accomplish this sound, Yoni enlisted the help of his brother on drums, Matt Meldon on guitar, and Doug McDiarmid as a random task member. The group toured much of 2005 in support of the album as a four-piece; however, by the time of their May 2006 tour with Islands, the group had become a three-piece, because Matt Meldon moved to an island off the coast of Seattle to live with his girlfriend.
WHY?'s discography consists of four full-lengths, four EPs, a number of singles, and a handful of limited edition CD-Rs. Further collaborative work has been done with a number of groups: Hymie's Basement, Miss Ohio's Nameless, Object Beings, and Reaching Quiet.
For their third LP, Alopecia, WHY? asked fans to contribute photographs of their palms for the album's artwork. The album was released March 11, 2008 to very positive reviews, with "The Hollows" as the first single. Two different European and US versions of the single were released, featuring remixes and covers by Boards of Canada, Xiu Xiu, Dntel, Half-Handed Cloud, Dump, and Islands on their respective issues.
On 22 September 2009 the band released their fourth LP, entitled Eskimo Snow. The ten songs on the album were recorded during the Alopecia sessions and are described by Wolf as "the least hip-hop out of anything I've ever been involved with".
The line-up for the band's live show currently includes two of the members from the band Fog. Andrew Broder is playing Guitar, and Mark Erickson is playing Bass.