Guitarist Greg McKenna actually started Letters to Cleo as another group; when he began searching for a background singer to complete his lineup, he found Kay Hanley. A powerhouse vocalist who had previously performed in a local new wave group, Hanley remained with McKenna after the original band fell apart several months later. The band adopted a peppy power pop sound as well as a new name, Letters to Cleo, which made reference to a pen pal with whom Hanley had corresponded during her childhood. Guitarist Michael Eisenstein (whom Hanley would later marry), drummer Stacy Jones, and bassist Scott Riebling soon completed the lineup, and the quintet spent several years touring the Boston circuit.

Now a seasoned band, Letters to Cleo saw their first full-length recording, Aurora Gory Alice, hit the market in 1993. The debut album was released under the local CherryDisc Records and fared much better than expected, which brought the band to the attention of major-label Giant Records. Giant issued a re-release of Aurora Gory Alice in 1994, followed by the sophomore recording Wholesale Meats and Fish one year later. Letters to Cleo also issued a pair of notable singles in 1995, "Awake" and "Here & Now," the latter of which received positive exposure on MTV and became a Top Ten hit on the Modern Rock Tracks chart. "Here & Now" was also used on the popular show Melrose Place, where it soundtracked the closing credits and eventually found its way onto the show's hit soundtrack. Even so, Wholesale Meats and Fish didn't do as well as its predecessor, and it would be two years before the next album, Go!, appeared. By this time, drummer Stacy Jones had parted ways with Letters to Cleo to join the group Veruca Salt (he would later launch his own band, American Hi-Fi), and Tom Polce had taken the vacant spot. The group returned in 1998 with Sister, which collected B-sides and material from early demo recordings.

Sister proved to be the band's final recording. Letters to Cleo played their last gig on May 4, 2000, and The Boston Globe officially announced the breakup one month later. However, having already inked a contract to complete work on Molly-O, an animated series for television, the bandmates partnered together for a brief period before going their own ways. Hanley piloted her strong vocals into a solo career. The singer also involved herself with various other projects, providing vocals for the Josie and the Pussycats movie (as well as appearing on its surprisingly endearing soundtrack) and singing backup vocals for Miley Cyrus' tour in 2008. Stacy Jones formed American Hi-Fi and also worked as a session drummer as well as Miley Cyrus' musical director and drummer; Riebling and Polce became producers and engineers, while McKenna founded another group, City Rivals. Letters to Cleo reunited in 2007 for a benefit for one of their most devoted fans, and embarked on a brief tour the following year, with Joe Klompus stepping in on bass for Riebling. After concentrating on their own projects for a few years, they reunited again for an appearance on the finale of the NBC comedy Parks and Recreation in 2014. Early in 2016, the band announced new music was on the horizon, and Letters to Cleo released the Back to Nebraska EP in October of that year. ~ Charlotte Dillon & Andrew Leahey