Granted, there have been so many. But I think you'll agree, this one takes the cake.
DC still has Oliver in his "pick a job, any job" phase. This week, he's opened a public relations firm!!
(3 boxes of paper clips? Jeez, Ollie, what the heck are you doing?!?!)
And, like in every single career he's ever had...he's flat broke.
So when he stops to pay the rent?
Don't ever change, Ollie...
From Detective Comics #555 (1985)