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When IDLE is run with an OS X Aqua Tk (Carbon 8.4 or Cocoa 8.5), using the File -> Recent Files menu item to open a previously used file causes that file to show up a second time in the updated menu item and with the same keyboard shortcut. With X11-based Tk on OS X, no duplicate is seen. The problem stems from a difference in the way the Tk versions generate sub menus. With the X11 Tk the sub menu appears to start with a separator in menu index 0 and the first file is added in index 1. With Aqua Tk, there is no separator and the first file is in index 0. The code in IDLE to update the menu deletes from 1 to END so, with Aqua Tk, the file name inserted into index 0 is not removed. The attached patch fixes the problem with Aqua Tk and appears to cause no problems with a current X11 Tk 8.5 on OS X. Before committing it, though, it should be tested on Windows, which I'm not currently set up to do.