Flight of the Conchords, New Zealand's self-proclaimed "fourth most popular guitar-based digi-bongo a cappella-rap-funk-comedy folk duo," first took shape in Wellington. Bret McKenzie and Jemaine Clement (musician/funnyman and funnyman/musician, respectively) started crafting their unique, two-man comedy mélange in 1998, while the two were living together as college roommates. Overcome by a dream in which a V formation of Gibson Flying Vs resembled a gaggle of Concorde airplanes, the two christened themselves Flight of the Conchords and began honing their act in local comedy and rock clubs during the late '90s. By 2002, they could be found playing such high-profile gigs as the Edinburgh Fringe Festival. When they returned to the fest in 2003, they were nominated for the Perrier Award, thus making them "the almost award-winning fourth most popular guitar-based digi-bongo a cappella-rap-funk-comedy folk duo in New Zealand." Between those gigs, Flight of the Conchords self-released the album Folk the World Tour, and by 2005 they had become the subject of a six-part BBC Radio 2 broadcast series -- a largely improvised affair in the vein of Spinal Tap and Tenacious D. Also in 2005, the group landed a spot on HBO's Friday night series One Night Stand.
Clement was featured in a series of humorous commercials for the U.S.-based Outback Steakhouse restaurant chain, and later that year, the band penned a deal with U.S. indie imprint Sub Pop. The label released the half-studio, half-live EP The Distant Future a year later. Shortly after signing to Sub Pop, the two got their breaks as actors. Clement scored a starring role in the indie romantic comedy Eagle vs. Shark, and HBO offered Bret and Jemaine their own series. Flight of the Conchords thus became a comedy show, and it premiered in June of 2007. Combining the understated humor of Ricky Gervais' Extras with the musical slapstick of Tenacious D's six-episode HBO series, the show followed the duo's attempt to achieve success as a band in New York City, with silly songs worked into the plot lines. After 12 well-received episodes, it was announced that the boys would return for a second season in 2008. That April, Sub Pop released a full-length album of songs from the first season. After another ten-episode run, a compilation of songs from season two was released in October of 2009, titled I Told You I Was Freaky.