As docs say it's impossible to add two menu items to NSPopUpButton if they both have the same title. I was trying to add menu items to [popupButton menu], but with no luck. I was also trying to create a new menu, add items to it and then use [popupButton setMenu:newMenu], but no. Menu always display only one item per name.
But I know it should be possible, if you try to create a smart playlist in iTunes, you could select "Playlist" from the left popup button, "=" from the middle, and the right one will hold menu items for every playlist in iTunes EVEN if they have the same title. So how do they do it?