I listen to pre-Sirius shows regularly and this is one of the biggest differences in the HSS back then.
Almost every day they had some kind of contest which was sponsored by a major company. For example "stuck on you" with Jeff and that little Hispanic woman provided a week of unbelievably funny and compelling radio. Then right after that they had Hollyweird Squares with Gilbert, Danial Carver, the woman from that crazy church that boycotts funerals (before they were even very well-known), etc. It was probably some of the best radio in the history of the format. Also a Stump the Booey or Win Fred's Money pretty much weekly.
Contrast that to the Sirius era of Tradio calls, Joan Rivers and AGT talk and it is pretty jarring.
Obviously the show declined mostly due to the replacement of Jackie, Billy, KC, John and Artie with Beth O, Shuli, Benji, John Hien and I'm Lisa Geeeeeee, but I also think the move to Sirius had a lot more to do with it than just losing out on A-list guests. The big name sponsors back then combined with the multitude of weirdos who would do anything to get on the air or win some money was a huge part of what made the show so good. And the constant barrage of gutteral, lisping f-bombs Howard can drop now that he's "uncensored" doesn't quite make up for it.
Sirius era is just filler.
The show is self going and uses the same script each day.
Howard News, Wrap up show clips, you tube clips, impersonate Kennedy/Mother and father, hate rant against all non jews and republicans, rant about how all non-jews should be aborted, fake Richard and Sal phone calls, fake fights, fake bits, fake callers.