This is tricky. I've found another user through google that has the same issue but I couldn't seem to find any resolution. Specifically, on my machine, EMMS will play tracks fine when Emacs in running in a terminal, but will not play tracks when running in a GUI environment.
When I enable debugging on error, the backtrace log shows the following:
Debugger entered--Lisp error: (error "Don't know how to play track: (*track* (type . file) (name . \"/Volumes/Users/Public/Music/iTunes/iTunes Music/Music/311/Don't Tread On Me/01 Don't Tread On Me.mp3\") (metadata) (info-artist . \"311\") (info-title . \"Don't Tread On Me\") (info-album . \"Don't Tread On Me\") (info-tracknumber . \"1\") (info-year . \"2005\") (info-genre . \"Rock\") (info-playing-time . 188) (info-mtime 19534 7550))")
signal(error ("Don't know how to play track: (*track* (type . file) (name . \"/Volumes/Users/Public/Music/iTunes/iTunes Music/Music/311/Don't Tread On Me/01 Don't Tread On Me.mp3\") (metadata) (info-artist . \"311\") (info-title . \"Don't Tread On Me\") (info-album . \"Don't Tread On Me\") (info-tracknumber . \"1\") (info-year . \"2005\") (info-genre . \"Rock\") (info-playing-time . 188) (info-mtime 19534 7550))"))
error("Don't know how to play track: %S" (*track* (type . file) (name . "/Volumes/Users/Public/Music/iTunes/iTunes Music/Music/311/Don't Tread On Me/01 Don't Tread On Me.mp3") (metadata) (info-artist . "311") (info-title . "Don't Tread On Me") (info-album . "Don't Tread On Me") (info-tracknumber . "1") (info-year . "2005") (info-genre . "Rock") (info-playing-time . 188) (info-mtime 19534 7550)))
emms-player-start((*track* (type . file) (name . "/Volumes/Users/Public/Music/iTunes/iTunes Music/Music/311/Don't Tread On Me/01 Don't Tread On Me.mp3") (metadata) (info-artist . "311") (info-title . "Don't Tread On Me") (info-album . "Don't Tread On Me") (info-tracknumber . "1") (info-year . "2005") (info-genre . "Rock") (info-playing-time . 188) (info-mtime 19534 7550)))
emms-start()
emms-playlist-mode-play-current-track()
emms-playlist-mode-play-smart()
call-interactively(emms-playlist-mode-play-smart nil nil)
I'm using Emacs 23.2.1 in Terminal.app on Mac OS X 10.6.4 when it works. When it doesn't, I'm using Emacs 23.2 from Emacs for OS X.