Ok... So below is what I came up with. The issue currently is that NodObjC doesn't allow me to specify protocols (or the implemented methods) for the NSWindowDelegate. In ObjC I would normally define this in < SomeProtocol > as follows:

@interface AppDelegate : NSObject <NSApplicationDelegate, NSWindowDelegate> {

There is a line in the example below: statusMenu('button')('window')('setDelegate', self); this would normally make the NSWindow "ask" the AppDelegate what to do for certain method calls..

This doesn't seem possible, or at least I couldn't find a way to achieve this.

var $ = require('NodObjC')
$.import('Cocoa')
$.import('Foundation');
$.import('AppKit');
$.import('QuartzCore');

var pool = $.NSAutoreleasePool('alloc')('init'),
    app  = $.NSApplication('sharedApplication'),
    statusMenu;

var AppDelegate = $.NSObject.extend('AppDelegate')

AppDelegate.addMethod('applicationDidFinishLaunching:', 'v@:@', function (self, _cmd, notif) {

  var systemStatusBar = $.NSStatusBar('systemStatusBar');
  statusMenu = systemStatusBar('statusItemWithLength', -1);
  statusMenu('retain');

  var title = $.NSString('stringWithUTF8String', "DragDrop");
  statusMenu('setTitle', title);
  statusMenu('setHighlightMode', true);

  var arrayDraggedTypes = $.NSMutableArray('alloc')('init')
  arrayDraggedTypes('addObject', $.NSFilenamesPboardType);

  statusMenu('button')('window')('registerForDraggedTypes', arrayDraggedTypes);
  statusMenu('button')('window')('setDelegate', self);
  console.log(self);
})

AppDelegate.addMethod('draggingEntered:', 'v@:@', function (self, _cmd, sender) {
  return $.NSDragOperationCopy;
})

AppDelegate.addMethod('performDragOperation:', 'v@:@', function (self, _cmd, sender) {
  console.log("WOWZA");
})

AppDelegate.register()

var delegate = AppDelegate('alloc')('init')
app('setDelegate', delegate)

app('activateIgnoringOtherApps', true)
app('run')

pool('release');

@niftylettuce; remember we where getting undefined on the statusMenu.button.window? I managed to get a reference to it by using statusMenu('button')('window') - just FYI

API for ability to drag/drop item to menubar event? #1549

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