Dando was born in Essex, Massachusetts, to Susan, a former fashion model, and Jeffrey, who worked as a real estate attorney. At the age of ten, his family moved to the North Shore of Boston; his parents divorced two years later. In his teens Dando attended Commonwealth School in Boston. In the fall of 1986 he enrolled at Skidmore College but dropped out after getting "four Fs and a D."\n', '

While at Commonwealth, Dando met Ben Deily and Jesse Peretz, and in 1986 they formed the Whelps before changing their name to Lemonheads, like that of the candy manufactured by Ferrara Pan. The Lemonheads debuted at the Meltdown House in Cambridge on July 18, 1986, followed by a show at The Rat on August 19. The band recorded an EP, Laughing All the Way to the Cleaners, which got the attention of Taang! Records, a local label. The Lemonheads\' first three albums, Hate Your Friends, Creator, and Lick, were all released on Taang!\n', '

Following the third album, Dando left the group briefly after some tension with Deily, and joined Juliana Hatfield\'s band Blake Babies. However, he returned as a drummer when The Lemonheads\' cover of Suzanne Vega\'s song "Luka" became successful, and the group had an opportunity to tour Europe. Deily, however, quit the band shortly before the tour, which placed Dando as the guitarist and lead vocalist. Dando brought in David Ryan on drums, and the group signed with major label Atlantic/Warner, where it released the album Lovey in 1990.[citation needed] The album straddled punk, rock, country, and metal,[need quotation to verify] and sold about 9,000-11,000 copies.[citation needed]\n', '

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