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Born in Princeton, NJ Osander was a member of the New York City jamband God Street Wine from 1988–1998, recording six albums and performing more than 1,000 shows across America and beyond with bands like The Allman Brothers, Bruce Hornsby and the Black Crowes.
In 1999 Osander moved to Killarney, Ireland, to join the alternative, Killarney-based rock band Poor Uncle Harry in the late '90s. After the popular though short-lived band folded, he began playing with Damien Rice in 2000 and over the next several years recorded both the albums "O" and "9". In the summer of 2007 he left Rice to concentrate on Lisa Hannigan's solo career. He recorded her solo album "Sea Sew" in 2008 and did several tours over the next two years in support of that release before taking a year off from the road in 2010.
Osander, with his partner Tanja Raab, have produced several benefit shows over the years under the name Double Donkey Productions. These include the 2004 Concert for Bam (in aid of the victims of the Stephens Day Earthquake in Iran) at Vicar St. in Dublin and the 2010 Thomastown Community Kindergarten Benefit featuring Paul Noonan and Gavin Glass at the Bridgebrook Arms in Kilkenny, Ireland.
- Budnick, Dean (1998). Jam Bands: North America's Hottest Live Groups Plus How to Tape and Trade. ECW Press. pp. 107–109. ISBN 9781550223538.
- The Killarney Kingdom, May 1999