Inspired by the AV club @TheOnion - there may be a fine line between acting and singing from the soul but I thought this'd be a fun list
  1. Sylvia's Mother - Dr Hook
    Perfect story song. Shel Silverstein will be all over this list
  2. A Front Row Seat To Hear Old Johnny Sing - Shel Silverstein
  3. Buenas Tardes Amigo - Ween
    Read about it on avclub.com The inspiration for my list
  4. That's Me Trying - William Shatner
    Amazing stuff. This whole record is brilliantly acted, especially little moments like before the last song : "can you do one more take?" "always could do one more"
  5. My Life Is Good / I Just Want You To Hurt Like I Do - Randy Newman
    So many Randy Newman songs can fit on this list
  6. The Piano Has Been Drinking - Tom Waits
  7. Drunk In Love - Beyoncé
    If she's supposed to sounds drunk as shit rambling through this song then mission accomplished
  8. Warren Zevon - (all songs)
  9. Bonnie and Clyde - Brigitte Bordot and Serge Gainsbourg
  10. The Sing - Bill Callahan
    Maybe it's just the lyrics
  11. Bang Bang - Nancy Sinatra