| 12/26/99 | 99-52 | The Dr. Demento Show #99-52 - December 26, 1999
Topic: The Funny 25 | |
| 12/19/99 | 99-51 | The Dr. Demento Show #99-51 - December 19, 1999
Topic: Christmas part 3/3 | |
| 12/12/99 | 99-50 | The Dr. Demento Show #99-50 - December 12, 1999
Topic: Christmas part 2/3 | |
| 12/05/99 | 99-49 | The Dr. Demento Show #99-49 - December 5, 1999
Topic: Christmas part 1/3 | |
| 11/28/99 | 99-48 | The Dr. Demento Show #99-48 - November 28, 1999
Topic: wintertime | |
| 11/21/99 | 99-47 | The Dr. Demento Show #99-47 - November 21, 1999
Topic: Thanksgiving/worst records ever made | |
| 11/14/99 | 99-46 | The Dr. Demento Show #99-46 - November 14, 1999
Topic: hunting | |
| 11/07/99 | 99-45 | The Dr. Demento Show #99-45 - November 7, 1999
Topic: hippies and psychedelia | |
| 10/31/99 | 99-44 | The Dr. Demento Show #99-44 - October 31, 1999
Topic: Halloween part 2/2 | |
| 10/24/99 | 99-43 | The Dr. Demento Show #99-43 - October 24, 1999
Topic: Halloween part 1/2 | |
| 10/17/99 | 99-42 | The Dr. Demento Show #99-42 - October 17, 1999
Topic: men | |
| 10/10/99 | 99-41 | The Dr. Demento Show #99-41 - October 10, 1999
Topic: women | |
| 10/03/99 | 99-40 | The Dr. Demento Show #99-40 - October 3, 1999
Topic: Stan Freberg interview; sports | |
| 09/26/99 | 99-39 | The Dr. Demento Show #99-39 - September 26, 1999
Topic: Stan Freberg interview | |
| 09/19/99 | 99-38 | The Dr. Demento Show #99-38 - September 19, 1999
Topic: alcohol | |
| 09/12/99 | 99-37 | The Dr. Demento Show #99-37 - September 12, 1999
Topic: serious contemporary singers and groups doing some definitely non-serious songs | |
| 09/05/99 | 99-36 | The Dr. Demento Show #99-36 - September 5, 1999
Topic: working | |
| 08/29/99 | 99-35 | The Dr. Demento Show #99-35 - August 29, 1999
Topic: big songs; college songs | |
| 08/22/99 | 99-34 | The Dr. Demento Show #99-34 - August 22, 1999
Topic: cats | |
| 08/15/99 | 99-33 | The Dr. Demento Show #99-33 - August 15, 1999
Topic: dogs | |
| 08/08/99 | 99-32 | The Dr. Demento Show #99-32 - August 8, 1999
Topic: the shortest funny songs ever sung | |
| 08/01/99 | 99-31 | The Dr. Demento Show #99-31 - August 1, 1999
Topic: Dr. Demento's zoo | |
| 07/25/99 | 99-30 | The Dr. Demento Show #99-30 - July 25, 1999
Topic: Dr. Demento's farm | |
| 07/18/99 | 99-29 | The Dr. Demento Show #99-29 - July 18, 1999
Topic: "Weird Al" Yankovic - The Running With Scissors Interview | |
| 07/11/99 | 99-28 | The Dr. Demento Show #99-28 - July 11, 1999
Topic: 25th anniversary of the Dr. Demento Show going national; fishing | |
| 07/04/99 | 99-27 | The Dr. Demento Show #99-27 - July 4, 1999
Topic: All-American show f/ brand new "Weird Al" Yankovic album | |
| 06/27/99 | 99-26 | The Dr. Demento Show #99-26 - June 27, 1999
Topic: 1988 (rerun of show #98-39 from September 27, 1998) | |
| 06/20/99 | 99-25 | The Dr. Demento Show #99-25 - June 20, 1999
Topic: alternate lifestyles | |
| 06/13/99 | 99-24 | The Dr. Demento Show #99-24 - June 13, 1999
Topic: babies | |
| 06/06/99 | 99-23 | The Dr. Demento Show #99-23 - June 6, 1999
Topic: marriage | |
| 05/30/99 | 99-22 | The Dr. Demento Show #99-22 - May 30, 1999
Topic: two wheels (bicycles & motorcycles); salute to Shel Silverstein | |
| 05/23/99 | 99-21 | The Dr. Demento Show #99-21 - May 23, 1999
Topic: salute to Star Wars Episode I: The Phantom Menace | |
| 05/16/99 | 99-20 | The Dr. Demento Show #99-20 - May 16, 1999
Topic: unreleased classics | |
| 05/09/99 | 99-19 | The Dr. Demento Show #99-19 - May 9, 1999
Topic: science and technology | |
| 05/02/99 | 99-18 | The Dr. Demento Show #99-18 - May 2, 1999
Topic: 25th anniversary of streaking | |
| 04/25/99 | 99-17 | The Dr. Demento Show #99-17 - April 25, 1999
Topic: that bump on your head with holes in it (your nose) | |
| 04/18/99 | 99-16 | The Dr. Demento Show #99-16 - April 18, 1999
Topic: the police department | |
| 04/11/99 | 99-15 | The Dr. Demento Show #99-15 - April 11, 1999
Topic: pro wrestling | |
| 04/04/99 | 99-14 | The Dr. Demento Show #99-14 - April 4, 1999
Topic: baseball | |
| 03/28/99 | 99-13 | The Dr. Demento Show #99-13 - March 28, 1999
Topic: Henry Phillips interview; music so demented it doesn't need words | |
| 03/21/99 | 99-12 | The Dr. Demento Show #99-12 - March 21, 1999
Topic: The Great Luke Ski interview | |
| 03/14/99 | 99-11 | The Dr. Demento Show #99-11 - March 14, 1999
Topic: hair | |
| 03/07/99 | 99-10 | The Dr. Demento Show #99-10 - March 7, 1999
Topic: computers | |
| 02/28/99 | 99-09 | The Dr. Demento Show #99-09 - February 28, 1999
Topic: more cartoon tunes | |
| 02/21/99 | 99-08 | The Dr. Demento Show #99-08 - February 21, 1999
Topic: cartoon tunes | |
| 02/14/99 | 99-07 | The Dr. Demento Show #99-07 - February 14, 1999
Topic: birds & bees/Valentine's Day | |
| 02/07/99 | 99-06 | The Dr. Demento Show #99-06 - February 7, 1999
Topic: 35th anniversary of the invasion of America by The Beatles | |
| 01/31/99 | 99-05 | The Dr. Demento Show #99-05 - January 31, 1999
Topic: cows & cowboys | |
| 01/24/99 | 99-04 | The Dr. Demento Show #99-04 - January 24, 1999
Topic: bears | |
| 01/17/99 | 99-03 | The Dr. Demento Show #99-03 - January 17, 1999
Topic: aliens and extraterrestrials | |
| 01/10/99 | 99-02 | The Dr. Demento Show #99-02 - January 10, 1999
Topic: Star Trek | |
| 01/03/99 | 99-01 | The Dr. Demento Show #99-01 - January 3, 1999
Topic: trains | |