I'm listening to 1/21/2003 and Howard and Gary are talking about the "special tape", a VHS tape of two girls going at it that they say is the greatest porn ever created. I did a Google search and couldn't find much about it.
I did find this 2005 article at howardstern.com:
In a stunning revelation, resident perv Richard Christy confessed to braking his “no pleasuring himself during the work week” rule last night. Christy described a “perfect storm” scenario of having to make copies of one of Gary’s special porn tapes, looking at the new issue of Penthouse for an upcoming guest, and the fact that yesterday was Valentine’s Day as the “extenuating circumstances” for the break down. Christy said that the “special tape” – a lesbian porn tape a fan sent in years ago of two, probably amateur, girls going at it – was the straw that broke this camel’s back though. He said he couldn’t get through five minutes of it without taking his right hand out on a date.
And thanks to MarksFriggin, when I get to 1/27/2003, this will be discussed:
Howard told the guys that Beth wanted to know what he was pleasuring himself to while she was away. He said he showed her the ''Special Tape'' that he watched and they ended up having sex during that. Howard said that Beth thought the women in the tape were pretty good looking and she understood why it turned him on.
My question is, well, quite obvious.