Thanks heidar-rafn for reporting this issue and sorry for the long time without response. Have you checked if this is still a feature of recent versions of Rhythmbox? You can try the last one with a life CD or USB of Ubuntu 14.04.
** Changed in: rhythmbox (Ubuntu) Status: New => Incomplete -- You received this bug notification because you are a member of Ubuntu Desktop Bugs, which is subscribed to rhythmbox in Ubuntu. https://bugs.launchpad.net/bugs/1170926 Title: Unable to have same song played more than once in a playlist To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/rhythmbox/+bug/1170926/+subscriptions -- desktop-bugs mailing list desktop-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/desktop-bugs