Songfacts®:

• Stone Temple Pilots lead singer Scott Weiland knew he was hooked the first time he tried heroin, and by the time the band was recording their second album, Purple, he was becoming a junkie but doing everything he could to hide his addiction. Many of the songs on the album express this lonely, helpless feeling, including this one.
  
  "Pretty Penny" tells the story of a mother and daughter who are both addicts. He made up the story, but based it on his own struggles. Weiland said it was his last try to convince himself and others around him that he was not an addict.
• The band's guitarist, Dean DeLeo, wrote the music to this song (Weiland wrote the lyric). It's an acoustic track they recorded in the living room of one of a friend of their producer, Brendan O'Brien. According to their drummer, Eric Kretz, Dean and his brother Robert DeLeo played acoustic guitars while Weiland sang it from a microphone in the hallway. People hanging around the house shook their keys to help create the rhythm, and some percussion parts were overdubbed later. They later tried recording it with electric instruments, but couldn't come close to the intimate feel of the live living room recording.