I've had this same symptom pretty much since upgrading to 9.04. Wasn't an issue 
in 8.10.
2.6.28-16-generic #55-Ubuntu SMP Tue Oct 20 19:48:32 UTC 2009 x86_64 GNU/Linux

rhythmbox debug output shows this right when the dialog box pops up:

(10:53:49) [0x358a1c0] [rb_shell_player_error] rb-shell-player.c:3423: playback 
error while playing: Failed to open output device
(10:53:49) [0x358a1c0] [rhythmdb_entry_set] rhythmdb.c:3266: queuing 
RHYTHMDB_ACTION_ENTRY_SET
(10:53:49) [0x358a1c0] [rb_shell_player_stop] rb-shell-player.c:3186: stopping


** Attachment added: "debug log when failing"
   http://launchpadlibrarian.net/35111354/rhythmbox-debug.txt

-- 
Listen Internet radio leads to "failed to open output device" sometimes
https://bugs.launchpad.net/bugs/397425
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