The Ben Stiller Show - 1992 With Bobcat Goldthwait - 1.2 was released on:
USA: 4 October 1992
This is the asker. I found a table that listed the exact release dates of every episode, minus the omakes and Wedding Peach DX. I added them to Wedding Peach's Wikipedia article.
The third one comes out September in 2011.
OJ Simpson The Trial - 1995 was released on: USA: 1995
Superman - 1996 Mxyzpixilated - 2.8 was released on: USA: 20 September 1997
Cartoon Cartoon Fridays - 2000 was released on: USA: 8 June 2000
The Daily Show - 1996 Bobcat Goldthwait 1-55 was released on: USA: 3 December 1996
The Daily Show - 1996 Bobcat Goldthwait 1-147 was released on: USA: 18 June 1997
The Daily Show - 1996 Bobcat Goldthwait 2-139 was released on: USA: 1 June 1998
Kevin Pollak's Chat Show - 2009 Bobcat Goldthwait 5-23 was released on: USA: 8 December 2013
Ben Stiller Uncensored - 2001 TV was released on: USA: 20 September 2001
The Stiller and Meara Show - 1986 TV was released on: USA: 9 June 1986
Spoilers with Kevin Smith - 2012 'Cause This Is Stiller Stiller Night 2-9 was released on: USA: 14 February 2014
The Ben Stiller Show - 1990 1-2 was released on: USA: 28 January 1990
Stiller and Meara - 2010 MariHuana 1-7 was released on: USA: 2 November 2010
Stiller and Meara - 2010 The Homeless 1-16 was released on: USA: 18 January 2011
The Ben Stiller Show - 1990 1-4 was released on: USA: 12 February 1990
The Ben Stiller Show - 1990 1-5 was released on: USA: 19 February 1990