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1.
A marijuana joint.

Most notably used in lyrics by the Beastie Boys and NWA.
I rolled me a wooler as I decided whether to crack open the Brass Monkey or the eight ball.
by Andrew S April 08, 2004
 
2.
The term of frequently not attending a Lesson or event due to having commitments elsewhere.

Can also mean frequent trips to a seaside town for the sake of it.
John: Where is our teacher today?
Steve: I dont know?
John: I hope he hasn't done a Wooler on us
Steve: i bet he has a meeting :p
by BACTUER March 29, 2011