Jumprope was formed in Boston in late 1995 by singer/songwriter Ad Boc (formerly of Miranda Warning and Beginners Only), Cindy Goh on bass and vocals, Tom Evans on drums and vocals, and Ad's sister Noelle on guitar and vocals. The band focused on melodic, concise pop songs with often an extra twist of rich jazz chords borrowed from bossa nova. A demo tape heard by Twee Kitten Records of California led to their release of the band's first 4-song vinyl EP, "No Happy Songs" in 1996. Their 1997 release, "The Pensive EP" came out on Japan's lauded indie-pop label, Motorway.

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