Thadeus A. Thomas was a real Yellow Pages salesman who wandered onto the set one day and tried to sell the cast and crew ad space. Gus Van Sant was so intrigued by him he asked him to appear in the film.
The "long dolly shot" in which the camera slowly pulls away from the window while Blake plays inside took seven takes to successfully complete. As the crew only had three pieces of dolly track, crew members had to take track from the front and run it around to the back while the dolly moved backward.
Gus Van Sant had originally intended to make a direct biopic of Kurt Cobain in the mid-1990's but Cobain's widow, Courtney Love, objected. Undeterred, Van Sant met with Love to discuss some ideas for the film, as well as her possible involvement. Though the two became friends and discussed the film for years, Van Sant eventually realized that Love was too devastated by Cobain's death to ever collaborate on the film or allow a biopic. He adapted his ideas into this fictionalized story.
This film, Gerry (2002), Elephant (2003), and Paranoid Park (2007) form Gus Van Sant's "Death Tetralogy", which he edited himself. This film centers on death by suicide.