From This Might Be A Wiki
- For the song, see 1999 - Cowtown Medley.
- Long Tall Weekend's July 19 release makes history as the first ever MP3-only album from an established band.
- The TMBG music video compilation Direct From Brooklyn is released on VHS.
- John Linnell's solo album State Songs is released near the end of October, followed by the accompanying single Montana in November.
- They Might Be Giants creates six songs with corresponding videos for ABC's summer/fall mini-series Brave New World.
- TMBG sells the most legal MP3s on eMusic out of all of the artists in their catalog, for all of 1999.