From This Might Be A Wiki
- For the song, see "1999 - Cowtown Medley".
- The TMBG music video compilation Direct From Brooklyn is released on VHS on April 27.
- Long Tall Weekend's July 19 release makes history as the first ever digital-only album release from a major artist.
- They Might Be Giants creates six songs with corresponding videos for ABC's mini-series Brave New World, which was broadcast from July to September.
- John Linnell's solo album State Songs is released near the end of October, followed by the accompanying single "Montana" in November.
- TMBG becomes the year's the most downloaded artist on eMusic. As eMusic was the largest digital music marketplace at the time, this likely made them 1999's most legally downloaded band in general.
- A leaked studio tape of numerous unreleased demos, Dial-A-Song recordings, and commercials allegedly originates from this year.