The 1999 Demo Tape refers to a demo tape that was first discovered on 2007-07-01 when it was put up for auction on eBay. An archive of that auction indicates the tape was sold a week later on 2007-07-08 for $565. The description of the item was: "This is a demo cassette that Regina Spektor sent me back in 1999. The track list, written by Regina herself, is 1. Chicken Song, 2. Braille, 3. Love Affair, 4. Cinderella, 5. School is Out and 6. Sunshine. If memory serves, all of the tracks are just her and her piano. The tape is great shape and was hardly played. She a great talent but not my cup of tea. I hope that this finds its way into the hands of one of her fans."

The cassette case itself featured the track listing and the text "for Fred" as well as "All songs written + performed by me (Regina Spektor) © 1999 Regina Spektor Producted by Joe Perry". It is currently unknown how the demo ended up online.

The 1999 Demo Tape is notable for a number of reasons. This tape represents the earliest known non-live recordings of Regina Spektor's music. Furthermore, the tape has ties to 11:11 via demos of the songs "Love Affair", "Braille", and "Sunshine" which would later appear on the LP two years later. Finally, the tape also features three songs which are unique to this demo and have not been publically seen again nor acknowledged by Regina in any way: "Chicken Song", "Cinderella", and "School Is Out".

Stylistically, the songs on the 1999 Demo Tape are reminiscent f Regina Spektor's other early work, notably Public Domain, Papa's Bootlegs, and 11:11.