"The Last Worthless Evening" is a song written by John Corey, Don Henley, and Stan Lynch. It was a single recorded by Henley in 1989 that reached #21 on the US chart. The song was included on Henley's third album The End of the Innocence that same year.
The song is rumored to be about actress Michelle Pfeiffer. Henley himself tells the story to concertgoers that he was at a Hollywood party in the late 1980s when, from across the room, he spied the beautiful blond "It girl" of Hollywood. She had just broken up with her husband and was sitting on a couch smoking a cigarette next to her recent co-star, Jack Nicholson. Henley says that he, like every man in the room, wanted to meet her. As he tells it, he walked up to the woman and asked if he could bum a cigarette. Without ever looking up at him she thrust a cigarette in his direction. As he slinked away, he says Nicholson chortled, "Well played, Henley." (Vegas, 2012). Pfieffer separated from her first husband, Peter Horton, in 1988 and co-starred with Nicholson in The Witches of Eastwick in 1987. The female protagonist in the music video is played by Clare Michelle Hoak, the daughter of Jill Corey and Don Hoak.