Dando was born in Essex, Massachusetts, on Boston's North Shore, to Susan, a former fashion model, and Jeffrey, who worked as a real estate attorney.

In the fall of 1986 he enrolled at Skidmore College[2] but dropped out after getting "four Fs and a D."[1] While at Commonwealth, Dando met Ben Deily and Jesse Peretz, and in 1986 they formed the Whelps[1] before changing their name to Lemonheads, like that of the candy manufactured by Ferrara Pan.

[1] Following the third album, Dando left the group briefly after some tension with Deily, and joined Juliana Hatfield's band Blake Babies.

[1] However, he returned as a drummer when The Lemonheads' cover of Suzanne Vega's song "Luka" became successful,[4] and the group had an opportunity to tour Europe.

[5] Dando spent some time in Australia to write songs with friends Nic Dalton and Tom Morgan, who later started the band Sneeze.

In 1992, The Lemonheads recorded a punk-inflected cover of Simon and Garfunkel's hit "Mrs. Robinson" to help promote the VHS release of The Graduate for the film's 25th anniversary.

[10] In late 1993, the group released the album Come on Feel the Lemonheads, which featured singles "It's About Time", "Big Gay Heart", and "Into Your Arms".

[17] Dando also had a lineup which included bassist Vess Ruhtenberg and drummer Devon Ashley of the Pieces where they toured the UK, Europe and the United States.

[18] In 2009 the Lemonheads released Varshons, a collection of 11 covers, including tracks originally recorded by Gram Parsons, Wire, GG Allin, Christina Aguilera; the album featured vocal performances by actress Liv Tyler and model Kate Moss.

[citation needed] Dando has worked regularly with Juliana Hatfield where he appeared on several Blake Babies songs and she in turn played with The Lemonheads.

[citation needed] In 1995, he had a small role in James Mangold's indie film Heavy, and contributed two cover songs to the soundtrack.

[citation needed] At the All Tomorrow's Parties' Don't Look Back festival, Dando played several live dates, including a full performance of the It's A Shame About Ray album.

[29] While taking a break from making music with/as the Lemonheads, Dando met English model and musician Elizabeth Moses in 1998; they married two years later.