Osander co-founded seminal New York City based jam band God Street Wine.

[2] In 1999 Osander moved to Killarney, Ireland, to briefly join the alternative, Killarney-based rock band Poor Uncle Harry.

[9] 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 Street in Dublin and the 2010 Thomastown Community Kindergarten Benefit featuring Paul Noonan and Gavin Glass at the Bridgebrook Arms in Kilkenny, Ireland.

With Damien Rice With Lisa Hannigan With God Street Wine With Herbie Hancock With Lo Faber With Hanna Leess With Sonny Casey With Eilon Freeman With Port Noo With Peter Doran With Crossmoke With Kieran McMahon With Margaret Healy