"40 Kinds of Sadness" is the third and last single Ryan Cabrera released from his 2004 multi-platinum selling debut album Take It All Away. The song was co-written by hit makers Curt Frasca and Sabelle Breer, the same team responsible for Ryan's biggest hit to date "On the Way Down". The song reached #32 on Billboard's Top 40 airplay chart. The music video for 40 Kinds Of Sadness reached #1 on the TRL countdown on May 9, 2005.